Inside monday.com’s transformation: radical transparency, impact over output, and their path to $1B ARR | Daniel Lereya (Chief Product and Technology Officer) - podcast episode cover

Inside monday.com’s transformation: radical transparency, impact over output, and their path to $1B ARR | Daniel Lereya (Chief Product and Technology Officer)

Apr 27, 20252 hr 32 min
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Summary

Daniel Lereya shares monday.com's journey to $1B ARR, focusing on a transformation spurred by competitors shipping faster. He discusses setting ambitious goals, prioritizing impact over output, and radical transparency, revealing how these strategies redefined monday.com's market position and culture. Lereya also touches on personal leadership challenges and the role of AI, providing insights for recognizing and driving change within growing companies.

Episode description

Daniel Lereya, the Chief Product and Technology Officer at monday.com, shares how he and his team realized they were being outpaced by competitors and how that realization completely transformed how they operate and allowed them to build a global powerhouse, doing over $1 billion in ARR, with 245,000 customers worldwide.

What you’ll learn:

1. How they used seemingly impossible goals, like building 25 new features in one month, to unlock bigger thinking on their team

2. How sharing real-time metrics with the entire company—even during interviews—created a culture of accountability and alignment

3. How focusing on impact, rather than just shipping features, has transformed the company’s culture

4. The story behind monday.com’s decision to launch five new products simultaneously and how it redefined their market positioning

5. How they use “traps” (timeboxed deadlines) to drive focus, avoid scope creep, and deliver faster

6. Daniel’s personal journey of navigating impostor syndrome and scaling challenges, and the mental models he uses to stay grounded and effective

Brought to you by:

Enterpret—Transform customer feedback into product growth

Airtable ProductCentral—Launch to new heights with a unified system for product development

Vanta—Automate compliance. Simplify security

Where to find Daniel Lereya:

• LinkedIn: https://www.linkedin.com/in/daniel-lereya-aa487646/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Introduction to Daniel and monday.com

(04:20) The pivotal moment: competitors shipping faster

(08:50) Setting ambitious goals

(17:44) Focusing on impact rather than features

(27:07) Transforming your product quarterly

(32:07) Scaling monday.com: challenges and strategies

(39:14) How monday.com maintains transparency as a public company

(45:40) The importance of taking risks

(51:02) Counterintuitive lessons in product development

(54:33) The value of timeboxing and deadlines

(57:28) Embracing user feedback

(59:54) Adapting leadership styles

(01:04:43) Personal reflections on leadership

(01:10:41) Handling crises and strategic planning

(01:17:28) The role of AI in work and personal life

(01:22:13) Final thoughts and lightning round

Referenced:

Monday.com: https://monday.com/

• The basics of a monday.com board: https://support.monday.com/hc/en-us/articles/115005317249-The-basics-of-a-board

• Eran Zinman on LinkedIn: https://www.linkedin.com/in/eranzinman/

• Roy Mann on LinkedIn: https://www.linkedin.com/in/manroy/

• Tal Harari on LinkedIn: https://www.linkedin.com/in/tal-harari-a2515215/

• Four-minute mile: https://en.wikipedia.org/wiki/Four-minute_mile

• A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals): https://www.lennysnewsletter.com/p/shape-up-ryan-singer

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• AI blocks: https://support.monday.com/hc/en-us/articles/18433811274386-AI-Automation-blocks

• Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of

• Behind the founder: Drew Houston (Dropbox): https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox

• SpaceX: https://www.spacex.com/

• Why and how to lead with transparency: https://monday.com/blog/monday-insights/may-30th/

• How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can’t copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra

• This Week #5: Overcoming impostor syndrome, introducing growth to an org, and how to partner with your data scientist: https://www.lennysnewsletter.com/p/this-week-overcoming-impostor-syndrome

• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/

• Bryan Johnson on LinkedIn: https://www.linkedin.com/in/bryanrjohnson/

• ChatGPT: https://chatgpt.com/

• Cursor: https://www.cursor.com/

• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

FIFA 22: https://store.playstation.com/en-us/concept/10002538/

Formula 1: Drive to Survive on Netflix: https://www.netflix.com/title/80204890

• Google Photos: https://photos.google.com/

Recommended books:

Shape Up: Stop Running in Circles and Ship Work that Matters: https://basecamp.com/shapeup

• Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595

No Rules Rules: Netflix and the Culture of Reinvention: https://www.amazon.com/No-Rules-Netflix-Culture-Reinvention/dp/1984877860

Nonviolent Communication: A Language of Life: Life-Changing Tools for Healthy Relationships: https://www.amazon.com/Nonviolent-Communication-Language-Life-Changing-Relationships/dp/189200528X/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

Lenny may be an investor in the companies discussed.



Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Transcript

A great PM basically for me is someone that is relentless until he gets this impact, until he validates that this impact. is in place in some cases doing the biggest impact is not developing another feature it's about making the current value more accessible you've been at this for eight years

You said there's 250,000 customers at this point. What would you say is the most counterintuitive thing you've learned through this journey of Building Monday? We really have an approach of very radical transparency about everything. Before we went public, we actually shared every bit

of information with our employees. Instead of demoralizing people, I think that this is something that gives them a sense of deep partnership. We really want everyone's brains in the challenge and not just one centralized brain and a lot of working hands. You basically realized that your competitors were

shipping a lot faster than you were. That made you shift the way you think about product and the way you operate. Some of our competitors did something that we can only imagine. We said, okay, we need to treat it differently. We received a gift from our competitors. They showed us. that it's possible. Use your competition, know it and take it and set ambitious goals and believe in yourself and you can do amazing things.

Today, my guest is Daniel Larea. Daniel's currently chief product and technology officer at monday.com. He joined when they were just around 40 employees. And a few years in, Daniel and the exec team realized that their competitors were able to move a lot faster than they were and ship a lot more often than they were. And that spurred a transformation in how they build and operate their team.

Very few companies are able to transform like this, and even fewer recognize that something is wrong. In our conversation, Daniel shares a bunch of very specific insights and suggestions into how to go about making change or even recognizing that something is wrong. Daniel shares moments when it felt like everything was going to crumble.

Why it's important to know that the skills that got you to where you are today aren't the skills that are going to take you to the next level. Why it's so important to orient all your teams around impact and so much more. if you enjoyed this podcast don't forget to subscribe and follow it in your favorite podcasting app or youtube

Also, if you become an annual subscriber of my newsletter, you get a year free of paid accounts at Superhuman, Linear, Notion, Granola, and Perplexity Pro. Check it out at Lenny's Newsletter.com and click Bundle. With that, I bring you Daniel Arreia. This episode is brought to you by Interpret. Interpret unifies all your customer from gone calls to Zendesk tickets to Twitter threads to App Store reviews and makes it available for analysis.

It's trusted by leading product orgs like Canva, Notion, Loom, Linear, Monday.com, and Strava to bring the voice of the customer into the product development process, helping you build best in class products faster. What makes Interpret special is its ability to build and update customer-specific AI models that provide the most granular and accurate insights into your business.

Connect customer insights to revenue and operational data in your CRM or data warehouse to map the business impact of each customer need and prioritize confidently. and empower your entire team to easily take action on use cases like win-loss analysis, critical bug detection, and identifying drivers of churn with Interpret's AI assistant wisdom.

Looking to automate your feedback loops and prioritize your roadmap with confidence like Notion, Canva, and Linear? Visit enterpret.com to connect with the team and get two free months. when you sign up for an annual plan. This is a limited time offer. That's interpret.com slash Lenny. This episode is brought to you by Airtable Product Central, the unified system that brings your entire product org together in one place. No more scattered tools, no more misaligned teams.

if you're like most product leaders you're tired of constant context switching between tools that's why airtable built product central after decades of working with world-class product companies Think of it as mission control for your entire product organization. Unlike rigid point solutions, Product Central powers everything from resourcing to voice of customer to roadmapping to launch execution.

And because it's built on Airtable's no-code platform, you can customize every workflow to match exactly how your team works. No limitations, no compromises. Ready to see it in action? Head to Airtable.com slash Lenny to book a demo. That's Airtable.com slash Lenny. Daniel, thank you so much for being here and welcome to the podcast.

Thank you so much for having me. We're gonna get into the story of Monday. We're gonna talk about your journey over the last eight years, building and scaling this company and all things you've learned along the way. But I wanna start with a very specific moment that you shared with me. where you basically realized that your competitors were shipping a lot faster than you were, able to get stuff out a lot more quickly and more often than you guys.

And that made you shift the way you think about product and the way you operate. Can you talk about that moment and that lesson and what you took away from that? Yeah, wow. You take me a while back, you know, and... I think it was when we were relatively a small team. I think we were something around like 30 people. And, you know, including engineers and product and everyone. It's actually that back in the days... We did so many things and actually we had an amazing, amazing execution.

We had a weekly update where we would share everything that we did with the company. And it was always super long and super like with so many different things. And we really felt good about ourselves at that point, to be honest about the execution.

And then I remember one day, you know, coming to the office and just looking on one of our competitors. And with Monday, we have like one of the main things that we have in the product is our boards. It's like... the heart and soul of the product and it's you can think about it as a table and it has different column types data types that you can capture within the board and work with and

You know, back then we had five of these and I was actually coding the sixth one, to be honest. And each and every one of these like took us like four months to develop, you know, together with defining the product and everything. And at this morning, we actually saw that one of our main competitors back then has actually launched 30 new columns. 30. Yeah. And, you know, we said... At first, we didn't really know what to do, and we thought about it, and I remember that...

Even we said, okay, we're going to take... even some time out of the office. So back then, Rory and Eran, which are the founders, and also together with me and Tal, which was one of the main tech leads in Monday for a long time. and a few others. We went outside the office and we said, listen.

we need to do things differently something doesn't make sense and you know i remember back then that for me this realization of like understanding that we are doing so much but suddenly some of our competitors did something that we can only imagine and actually transform the product because it's a different type of platform if you think about it. It was really hard, personally. First of all, admitting that although you worked like crazy

You didn't do something that really transformed the product because I remember back then when we did a conversation, we said, okay, we're doing so much. What is the most meaningful thing that we did over the last three months? And you know, suddenly the answer was, you know, there's so many things, but it wasn't something specific. And...

After acknowledging that, and it's a very hard thing personally, especially when you work so hard and you put your entire heart in what you do, we said, okay. Now... we need to treat it differently. We receive the gift from our competitors. They showed us that it's possible. Now we need to think how. And in order to do that, we need to think differently. Because remember, like we said, okay, if we are going to add 25 more, multiply it by 4 months.

we're a small team we we lost okay we can't make it so We said, okay, we need to take upon ourselves an ambitious goal, like... 25 columns in one month. And this is the goal that we took upon ourselves. And, you know, I think that the fact that our competitors did it gave us like... didn't give us the excuse of saying it's not possible. So in a way, it was the biggest favor that we can ask for. And, you know, long story short...

We had 30 columns in Monday and we did it, you know, by thinking totally different. And by the way, afterwards, you know, we did it over and over again. So if you think about Monday, it's basically a platform for work and you have different building blocks. Columns is one of them, but we did the same deal exactly with dashboards and widgets and then with automations and so on. So I think this was so transformative because A, we understood that...

You need to constantly think, especially at these phases, how would you transform completely the product in the next three months? And if you can't answer that and you say, listen, I'm doing so much thing, but you can't point this exact thing. you have a focus problem in my eyes and second that is that you know

it will make you think differently. And, you know, we really love now to do it, even when we don't know it's possible. And it actually works for us time after time. And last thing about it, you know, the team that was there. suddenly became invincible. Because, you know, it's such an amazing, amazing experience that you have a goal that you don't know how you're going to do it, and you succeed.

And then it makes you feel that everything is possible. There's so much here. And I have so many threads I want to follow on. One is just there's the kind of there's this metaphor of the four minute mile where no one thought it was possible. And then someone did it. And then everyone started beating that record. So I like that this is highlighting there's just so much power in seeing somebody else accomplish something you thought was impossible and that unlocks the way you think.

And I love that you saw it as a gift. A lot of people, a lot of companies do this. They're in this place and they're like, no way. It's like when the iPhone launched, like, no, no one, no one needs that. That's not good. There's no keyboard. And a lot of people like are like deny that. a thing they should be paying attention to i love that you saw it as like okay we need to We need to move. Things have changed. We're not doing things. We're not going to be competitive long term.

I think it's also very much about focus. And I think that, you know, it's very hard to get to a very good execution, but it doesn't guarantee that you are working in the right way. And many times in my eyes, you know, simple questions can provide the most and the deepest insights about your work. And I think that for us, The fact that we managed to leverage it, as he said, and see it as a gift is one of the most important things.

Use your competition. Know it. Use it to your advantage. And, you know, take it and set ambitious goals and believe in yourself and you can do amazing things. Another, I think... A lot of people are probably resonating with here is starting a company that's small, growing, things are going great. And then all of a sudden things start to slow down.

And in some cases, you don't realize that they've slowed down. And that's what happened to your case sounds like. In a lot of cases, the founder is like, what the hell is going on? Why is it taking three or four weeks to ship one type of new column? And so is there anything, by the way, what was the scale of the company at this point? It's a good question. if i'm not mistaking it was around uh 2018 uh back then how

It's safe to assume like 150, 200 people in the company, but we were relatively small. I recently had Ryan Singer on the podcast who created the ShapeUp method from Basecamp, and that's kind of his.

uh piece of advice too is around like 50 to 100 people things start to really change and slow down and that's where a lot of companies start to go sideways so that resonates that's really interesting and by the way this these columns you're describing just to make it clear this is like a new type of like data like new format of column like it's a new data format that you're building it's not like just add another column to some database

Yeah, so actually, exactly. It's a new type of column, but it's a whole product around it. If you think about it, for instance, you have a column that captures dates, so it's pretty straightforward, but you can also have formula columns. which is like more complicated and has like more complex product around it i think one of the best benefits for us as platform is that suddenly when we will like When we set the goal of adding so many different columns.

We actually stopped for the first time and say, what is a column like? And we also like organized all the product architecture around it. And you know, these kind of things like sounds really trivial in retrospect. We really defined, okay, each column needs to have like specific capabilities. It should be able to export it to Excel. It should be able to be filtered and sorted and so many different other things. But basically we defined.

what is it, and then create an infrastructure for all these shared things, making the work of adding a new column just thinking about the specific product that you want to provide with each one of these columns. And the story about it is actually even more interesting. The way we actually achieved it is that we said, okay, in two weeks, we are going to have an hackathon in which each one of our developers is going to take one column and implement it in one day.

And you know, if you think about it, from four months to one day, It's like mind-blowing. And back then I remember people said, how can it be? But then... that i told you about build an infrastructure he sent it to me i did a column at night you know just to to see the how the how it works and On the day that we did the columns, like everyone knew what they are going to do, what they are trying to solve. And we just did it. And two weeks afterwards, it was in production, which was amazing.

What we want to do here is help people avoid these moments where they're almost like too late and realizing that things have slowed down. So I think a really another important lesson here is the power of ambition and thinking crazily big. A lot of people think that when you ask your team, we need to build 25 columns in a month or whatever it was.

People would be like, I burned out or feeling super depressed. But really, people get excited. There's all this opportunity to think really differently. It reminds me at Airbnb, Brian Chesky was very famous for you give him a goal. Here's our goal for the year. And he's like. What would it take to 10x this goal? Just like, what would it take to do that? And he's always. pushing you to think a lot bigger when you're like, because your first reaction is like, What? No, no.

Leave us alone. But then you realize if you really think big, it changes everything about how you approach the problem, as you described, where it's like instead of like in a day, what would it take to build this in a day? Yeah, and I think, by the way, this is something which is really important about setting ambitious goals. If you set a different goal, I want to reduce it from four months to three months. So many times this translates in people's heads to I want you to work harder.

I want you to work longer hours. And this is not a message here. It's about working smarter. And I think that many times when we talk about speed of execution... You know, there's fake speed, which means trying to do the same work by skipping stages or not doing the high quality that you want. But there's the real speed and speeding. like organizations and speed of execution, many times it's about doing things right. It's about understanding.

A, what is going to move the needle and work only on that, not working in a lot of things that you tend to invent when you're trying to solve a problem. And B, is like, you know, about like thinking, as you said, like thinking differently. And I think that for the goals, this is why we really wanted the goal that you really understand from.

the first minute, that if you work the same way, you cannot achieve it, even if you sleep in the office. So you need to change dramatically how you think. And you know, the advanced phase of it is that today... We are doing it on things that we didn't see others doing. And, you know, we have the confidence because we have the experience of like trusting ourselves that.

This is an exercise for us that will make us actually think about different solutions. I know another element of this that is really important to you that you have shifted the way you all operate is focusing on impact. There was a lot of focus on just building a lot of stuff. And you realize there's a lot of power in thinking from perspective. How do we have the most impact? Talk about that. This is the core and the main thing that we also measure like our teams.

And this is how I see a great PM. So a great PM basically for me is someone that is relentless until he gets this impact and until he validates. that this impact is in place. And for us, it really changed how we think about things. It really changed how we set goals for our teams. So in many ways, BM in my day, first and foremost is...

responsible for creating the shared understanding on what would be impactful for our customers. Okay? It's not about the solution and what we are going to build. It's about what's the problem? What's the opportunity? And second... how we will know that we move the nailer and without these two things you can build so many different things and you know it's like songs for the draw like i built so

You know, such huge part of what I build was never used by users the way I thought it was going to use. So I think that... For me, having the misunderstanding of what we want to change for our customers and also how we know we did it is a huge, huge part of the PM role. And for us, you know... It means that we pay a lot of time in setting goals. in making sure that we really understand both again the opportunity but not only that but how we'll see

And we know for sure that we move the needle. In many ways, you know, it changes the conversation. So PMs, you know, and their teams, many times like... spending a lot of time at the problem area before they think about the solution. The solution is not the case anymore. It's not like there are so many different solutions.

And once you do that and you have these goals, suddenly it reduces also a lot of the discussions that you have about the different solutions because everyone knows that everything is going to be tested. on real life so they make make it everyone treated differently and also in that way you know it makes you think much more holistically, which I also think is something that is very special at Monday, is that we give our teams real-life goals as much as we can.

And then, you know, in some cases doing the biggest impact is not developing another feature.

It's about making the current value more accessible. It's about connecting better to the go-to-market motion that you have. It's about understanding how your customers are going to learn what you built and use it and you know this realization is something that we try very hard to stay on it and it's hard because like people tend to build things like we all love to build things right and when you start to build things you get excited and suddenly

you lose track of why. Why are you doing it? And what do you need to change? And I think that in that sense, this is the most important part about like... this point of impact and you know this is also how we measure ourselves so we can work extremely hard It doesn't mean that we are successful. It doesn't mean that we are doing our work right. Okay? And it's not only for the PMs. It's for the entire team. So the entire team...

succeeds or fail together based on the value that we bring to our customers. And we have a lot of like. different ways in order to make sure that we stay honest to this principle. There's a lot of people listening to this that work at, say, modern tech companies, very high growth tech companies that are just like, duh, this is how you should work. A lot of people hearing this are like, I don't really understand what like how like what am I doing wrong? What am I missing? Maybe.

What's a sign that you're not oriented around impact? I think the most obvious sign for me is that... you are building something without the aim or without the initial aim of what it should change for your users and how you are going to measure it. So in my eyes, it's many times the fact that you don't have a goal or the goal is like...

Many times, you know, for me, a smell for that is that I hear people use the word, we're going to enhance, we're going to augment, we're going to extend value and this and this and that. No, it's not enough. what is it going to change for users and how you're going to see it, that it actually happened. And then you start asking yourself all the questions, right? Because once you have a goal that you're committed to,

suddenly you think about the target audience because you need enough, like big enough target audience, for instance, in order to get to your goals. You need to make sure that... what you build actually going to touch all of these people. And I can share just a recent example, you know, and, you know, these things sound trivial and maybe an example would, you know, like help resonate with that because I know many people are thinking like that.

And, you know, we have a very, like, interesting offering that we just introduced with AI. It's called AI Blocks, okay? And basically, it means that with no code, you can integrate... blocks which contain AI actions within your existing workflows. And you know, 70% of Monday's customers are non-tech.

And for them, this makes AI accessible for them and has a huge, huge value. And we started building these blocks and we released it to customers. And we measured, you know, discoverability and adoption and retention and so on. And something that we do in order to stay connected to the numbers. So each team at Monday has like what we call the daily numbers update.

So we have a, think about it like a message that the team is building with all the numbers that they care about, because we really want people to leave these numbers. So for AI, for instance, for the AI blocks, it was the AI actions. So we had the AI actions, how many accounts are we using these AI actions and so on and so on. And, you know, we got amazing responses from our customers. We see great success of them getting value from their action.

But one day, we use a Slack channel in which one of our internal systems, BigBrain, is sending us these messages every day. And then we have conversations about it, okay? And, you know, one day we saw, we noticed that the amount of accounts that are using AI is super, super low comparing to the entire population that we have. And you know, we have 250,000 paying companies that use Monday, and we saw only like few thousands there.

And, you know, until this point, everyone will, like, in a very good feeling that we're making an amazing product, we get really good feedback, we're building great value, we're adding value. we sat down and say okay why it's only like this and this then someone said yeah you know since ai is new

We need to do change of the terms of service for customers before we are opening it to them. And this is planned, you know, for like... in the next quarter or something like that and said what no we need to do it now you know we need to now open it for everyone because this is actually what would be the most impactful thing to do. And then, like, you know, the team...

went and sent with legal and sent with everyone. And with two weeks time, it was open to 98% of Monday customers, you know. And I think in that sense, you know, this is a very good example because we could have continued building value. and it's great, but the impact wouldn't be the impact that we were aiming for. And this is a very important point. And you know, we...

I think in that sense, staying really connected to your numbers, this is something that I really feel strongly about. I feel that you need to get... your numbers in push. You need to live by them. You know, for me, it's like so exciting to see a conversation that says, oh, wow, today... There were a lot of new accounts that are using what I'm building. Let's see why it happens. And, you know, these kind of things that I see the conversation about.

It's amazing. And also, you know, in this case, seeing the AI actions go, it's like you want to dive it and push it forward. And in many ways, they feel that... This is a very good example on where you can actually build a lot of value. You can work really fast, you can deliver a lot of features, but the problem lays in other places in order to get the impact that you want. Yeah, there's so much joy in watching her number go up. So just to close the loop here.

to help people see if they're impact driven. working from a perspective of how do we drive the most impact is one simple way of thinking about it is you're working backwards from a goal that is going to drive business growth and revenue basically in the end. If you're working backwards from a number and a metric and a goal, and then thinking through what are the levers that will most move this metric.

That's a sign you're thinking impact by impact versus let's just keep shipping features that the sales team wants. Yeah, and I think another thing for me, like it's an exercise that I really, you know, I really encourage everyone to do. For me, it was like... After the columns hackathon and everything that we talked about, I said, okay, each quarter, and this is when we were much smaller, but it can be each month, it can be each two weeks. How do I imagine the company and the product?

is going to be different and better for our customers. a quarter from now. And from that, you know, work it backwards. But if you are just saying, we'll have better security, we'll have better performance, we'll have less bugs, we'll have more like enhancements to the, I don't know, this and this feature.

you need to constantly build value, which is pivotal to your customers. And if you don't do it, and if it's hard for you to answer about this question, it's a very good sign that you are not input driven. And you know, I love to do it.

also with teams and individuals like what are the things that you are most proud of that he did in the last three months and if it's like takes you a lot of time to think you're not very focused and you're definitely not maximizing the impact that you want due to that, in my eyes.

Like versus waiting for your competitors to do something and then realizing shit would be way behind. It's forcing yourself every quarter to think about this. So do you do this as like you have a meeting or someone in your calendar? Or how do you how do you actually operationalize? So it's actually, you know, today we are like under the builders organization, which is the engineering, product management, product design was 700 people.

So we have a lot of different ways and methodologies to do it in different levels. But I'll give you an example from the company level and from the team level, maybe, because these are the most interesting ones. We just recently had an early kickoff. Each and every year, we do an early kickoff for our company. And one of the most exciting sessions, obviously, is what we're going to do with our product as a product company. And I really like to have a slide in which I write and I just share it.

when I'm going to stand here in an ear form now. what is going to be different for our customers. And, you know, this is on the company level and I have one slide and it talks about like our offering and it talks about the value that they are getting in a way that next year... I want to you know each year to start my presentation with the slide from last year and see where we are.

And, you know, in this level, it can be something like our CRM continues with a very strong momentum and becomes a product suite when we give much more robust value to our customers. This can be an example, okay, with an additional product of... CRM marketing, I would just say. But on a team level, what we did, and maybe I'll take an example from the early days, you know, we really did, we really loved to do each and every two weeks.

I told you we would write like an update for the entire company about what we did. And the way we did it is that each and every one of our team members actually wrote his highlight. Then we would share it with the company and this exercise really made us sit every two weeks and think on an individual level, but also on a team level. And you know, every one of our team members used to read these updates and say, Dan.

We had a good two weeks or we had a bad two weeks. We did a lot of impact or we did not enough impact. So I really encourage to create these points in time where you sit down and you force yourself to understand whether... what you did is what you thought you're going to achieve or not.

That's great. I really like the slide idea. It's basically there's all this power in just working backwards from something in the future, however you come up with it. So it's just like in a year we're going to have this just like working backwards from a goal, working backwards from a big vision.

I think those are such good exercises. Obviously, Amazon's famous for working backwards. There's a whole book called Working Backwards from their PR approach. Okay. I want to go in a slightly different direction. I want to zoom out a little bit. So you've been at this for eight years, building Monday.

You said there's 250,000 customers at this point. What's like the revenue scale? Give people a couple stats to give them a sense of just how large this company has gotten. We recently announced that we cost the $1 billion in ARR. And we are serving, as I said, 250,000 customers across the globe from virtually any industry that you can think about, like more than 200 different business verticals it could be. both tech and non-tech savvy customers. The vast majority of our customers are non-tech.

And, you know, from like a customer that is building airplanes and cruise ships all the way to real estate, construction, finance. tech, and everything you can basically think of. And if I, like, just for reference and seeing our growth pace, so when I joined Monday eight and a half years ago, where we... Back then we were called the Pulse. We had around 4 million in ARR and we, you know... scaled from there to 1 billion and from around 30-40 people at the company to 2,500 right now.

Awesome. When you talk about the product you're building, to a lot of people, it's like, oh, it's like project management software, all this. Call him like, what's the big deal? But I had Drew Houston on the podcast and he made this really interesting point when he talks to people working at SpaceX who are like launching rockets to Mars.

And he talked about people building ships. Like if you really boil down, what are they doing day to day? They're sitting in tools like Monday, putting together tasks and doing to do's and sharing documents. Like this is kind of what the world runs on. So it's important to have that perspective. With that, putting that aside for a second.

I think very few people have seen what you've seen. Seeing a company scale this way. Also, the transformation you just shared of just like almost shipping too much and being slow to like, okay, let's rework things to shipping. 25 columns in a month and all these things. Like very few people have seen this. So there's a lot to learn from this journey that you've been on. So I have a bunch of questions and a bunch of different ways of approaching some of your biggest lessons from this journey.

The first is, let me just ask you this question. What would you say is the most counterintuitive thing you've learned? about building product and leading teams through this journey of building Monday? Maybe first of all, is about like something that we really care about, which is transparency. I'm like, let me tell you a story. Like I sat down for dinner at my family and many, many different members of my family are like entrepreneurs or like working as an executive in tech companies and so on.

And, you know, back in the days with Monday, before we went public, we actually shared every bit of information with our employees. You would get into our office. and you would see a dashboard with how many paying accounts you have, how many people have chained today, how many signups do we have, and so many different things. Even if you... came for an interview you'd see these numbers and I remember sitting in this dinner and everyone would tell me listen

You are making a mistake. How can you do it? When things go south, you know, you'll demoralize the team and people, like, you know, will get upset about it. And I think this is, you know, for me, one of the most important things when you hire and you have such a talented team. We want to share them. We want to share with them everything. And the reason for that is that...

then you are working on every challenge together. And instead of demoralizing people, I think that for the right people and the people that like, you know, are working at Monday. This is something that gives them so like you know a sense of deep partnership. And as a leader, you know, there were many situations in my professional life that I knew some bit of information.

And I felt, you know, all the weight on my shoulders. And I love to call it the dark side of the moon. You're there alone, right? Like you're coming to the office. There's nothing, you know, like more demoralizing or like... depressing as a leader that you feel awful because something that you know. And you're coming to the office and everything is great and everyone is happy. And I think in Monday, we really wanted to do it differently.

really have an approach of like very radical transparency about everything. And this actually makes everyone part. of what we are doing and in a way we like to say we really want everyone's brains in the challenge and not just one centralized brain and a lot of working hands and i can share examples you know when for instance Suddenly, people would come up to the office. We have dashboards across.

everywhere in the office. Like each team has its own dashboards. We have our company dashboards for metrics and so on. And I remember cases in which someone said, listen, what happened to the conversion? And you know, think how powerful it is. When you have everyone at the company looking at these things and many of the things that we discovered, many of the things that we saw as challenges and problems is things that people saw due to this transparency.

Maybe the, you know, counterintuitive part is that... Don't be afraid to share the information. It's exactly the other way around. And I can probably share that, you know, even today as a public company. We really share everything that we can, you know, and also like if you are a product manager at Monday, you are signing like a 10b5 program for selling your stocks, meaning that...

We found a way to make everyone still see the data because we think this is the most important part. And I think this is one thing that I really believe in and really changed how we work and also how people are feeling about. being partners in Building Monday and not just working at a company. Is that thing they sign that's just like auto sell stock, so they're not selling based on information, based on announcements that's coming? Okay, got it. So every PM basically has to automatically...

I can't like decide I'm going to sell my stock tomorrow because this number is tanking. Yeah. So, you know, like we want to give people a choice, but like usually we really feel that in most cases, you really need to know this information in order to do your work. That's so interesting. And I think people even prefer just like dollar cost average sell, you know, it's like, it makes life easier not having to try to time all these things. I definitely think so. Yeah. That's really interesting.

And that's just product managers or how far does that all go? No. So basically when we became public, you know, I remember still like one of the conversations that we had with... like the bankers and the lawyers about like, listen, guys, things would need to change. You cannot have a dashboard with all your financials at the entrance of the building.

It doesn't make sense as a public company. And we understood it, but we didn't want to let go of what we cared about because we really believe this is one of the main drivers to the business, having this transparency and having this shared brain. you know, mode. So we tried to think about ways in order to do it.

Now, if I like fast forward, you know, we're almost four years public and we have an internal app called Monday Morning. And in Monday Morning, you have two parts, part A and part B. Part A is for the every...

a company employee, contains a lot about engagement and a lot of data that can be shared with everyone. And part B is confidential and it's by role. Okay, so it's the company management. But I think the important point is that... we see product management as something that got to have these numbers so we thought about it really hard and you know it's a it's a lot of logistics to do like so many plants Yeah, 10b5 plants, but I think it's worth it.

This is so interesting. Like a lot of companies talk about transparency and you guys are I think radical transparency is a good way to describe this because I've never heard of a company. doing this. They didn't hear about it as well, apparently. And yeah, it took time to, you know, to get to the solutions. That's so funny. So for people that are listening to this are like, hey, maybe we should explore this. What's like one thing you'd suggest they?

that they could do to start moving down this road. And the benefit, again, is you, I guess, maybe again, remind people of the benefits of doing this, because it sounds like a lot of work and risk. When we were very small, you know, back in the days, we had like the daily numbers concept that we now have for the teams. We had the daily numbers for the company. How much bank accounts, how many upgraded, downgraded and so on daily.

And you saw people reacting to it like on a daily basis. So this is something that you can do in virtually one hour. It like changes how people... See, you know, they're all within the company. It focuses everyone to the company's KPIs because everyone understands what you care about and so on. So this is one thing that you can do extremely fast. And I don't see any disadvantage.

Aside from the fact that people are afraid, many times you are afraid. And I can share, like, it's so much, like, it's even, like, a big relief that you don't need to think, can I share it? Can I don't share it? Can I, like... You just let it go and everything would be okay. And I can share from my experience that we shared everything. And the second thing, which is really practical, you know, it's the office dashboards. We really believe in it. So, you know. you buy a tv you put it on the wall

You start a conversation due to it. What do we want to show on this TV? And you know, when we was like a smaller startup and we sat all in one office space, we had our company goals. And it also had like, we programmed it to have sounds on meaningful events. So when you had like, for instance, new paying account, you had the Homer Simpson saying like the same with the $1 million, I'll become a millionaire or something like that. uh for you know a new sign up you had the tick and so on so

suddenly everyone are leaving it, you know, it becomes part of the cadence of the company. So these are just two ideas to make it super easy. And the change happens immediately. I love how that connects back to the whole point about impact. People all lining around here is what we're trying to drive. Like if the Simpsons sound is going off, that's a sign that this matters. And this is something we should be driving up.

And it creates such a partnership. You know, I remember like reaching to the first time where we had one million dollar collection in one month, breaking the record of like new paying accounts for one day. Everyone are living. What in many companies, you know, only the management or the founders are like feeling. And I think that in that sense.

you already feel that you have a great power because everyone around is the same things and it makes conversation is different because everyone understands what matters to you at that point. This is awesome. Really cool counterintuitive lesson. I feel like a whole podcast could be done on how to do this effectively.

I want to move on, but I guess if people want to start implementing this at the company, let's just say they should go talk to you and you could give them a bunch of advice. I would love to. This episode is brought to you by Vanta, and I am very excited to have Christina Cassioppo, CEO and co-founder of Vanta, joining me for this very short conversation. Great to be here. Big fan of the podcast.

Vanta is a longtime sponsor of the show, but for some of our newer listeners, what does Vanta do and who is it for? Sure. So we started Vanta in 2018, focused on founder helping them start to build out their security programs and get credit for all of that hard security work with compliance certifications. SOC 2 or ISO 2701. Today, we currently help over 9,000 companies, including some startup household names like Atlassian, Ramp, and Langchain.

start and scale their security programs and ultimately build trust by automating compliance, centralizing GRC and accelerating security. That is awesome. I know from experience that these things take a lot of time and a lot of resources, and nobody wants to spend time doing this. That is very much our experience, but before the company, to some extent, during it. But the idea is with automation, with AI.

We are helping customers build trust with prospects and customers in an efficient way. And, you know, our joke, we started this compliance company so you don't. We appreciate you for doing that. And you have a special discount for listeners. They can get $1,000 off Vanta at vanta.com slash Lenny. That's V-A-N-T-A dot com slash Lenny for $1,000 off Vanta. Thanks for that, Christina.

Thank you. Any other big counterintuitive lessons from the journey that you think would be fun to share? One thing I really love about what we do in Monday is that we really love... to take risks not for the sake of it but we are not afraid to do bold moves And many times when you want to do bold moves, you have a lot of concerns, especially when you start to be successful, because you're afraid that you are going to break everything that you built till now.

And for me, you know, one of the most pivotal moments in the company life is when we decided that, you know, back in the days, as you said, we were a platform, but we had to go to market of a project management tool. And we said, listen, people are doing so many different things on top of Monday. They are building a CRM with Monday and they are building a software for managing their dev cycles and they are building so many different things.

And we took a decision, strategic decision to become like a multi-product company, which is built on top of this platform. We actually did something which is really counterintuitive. You know, the first thought that comes to mind, at least for me, is why maybe not just launch a new product, do it?

relatively on the side, gradually understand if it's successful. And if it would be successful, double click on it. But we actually did it in a very different way. We actually announced five different new products.

Simultaneously on the same time and you know we had so many like I can't stress enough how to think about it because like i remember when we talked about and doing it people say what but we are going to confuse our current users and it's going to have conversion and how are we going to do the marketing now when we have so many different go-to markets And the sales, they don't know how to navigate people to different. And what about pricing? So many different concerns.

But we decided to do it because we really want to create a pivotal leap. And I think that in that sense, you know, fast forward to this day, like part of these products were really successful. For instance, Monday Cell CRM is like... like going faster than Monday back in the days, like, you know, and it's amazing to see it.

And some of them, we understood that they don't need to be separate products and we collapsed them back to the main product. But the point is, is that we managed to learn and to change. both internally at the company, the perception of everyone around what we are building, but also externally. Like this move changed.

dramatically, the competitive landscape that we live in. And, you know, I think there was a lot of friction. Many people at the company were like having a lot of friction with it. It was really, really hard. But looking back... It's such, I'm so happy with this move and the fact that we did it like that because just imagine what would happen if we would choose one of them and it wasn't the successful product.

And our conclusion can be that multiproduct won't work for us. We really managed to transform the company in a very short amount of time and also to create new reality. And I think that... People need to remember that, and I'm constantly reminding it to myself, and I think this is something that we are constantly working, you know, with each other in order to make sure that we remember that not taking bold risks. not making bold moves, it's a risk for itself.

Okay. And many times, like, you know, people want the inertia and people want just the incremental value. But if you want to do lip. Many times you need to let go of things that were successful for you in the past. And this is very counterintuitive. And we did a lot of, you know, a lot of mental models to help us. cope with it. So I remember that when we were small and we had, for instance, like 20,000 paying customers.

So he said, listen, but most of Monday's customers are not customers of Monday yet. So we need to think about them as well. You know, and this is something that really helps you because many times you need to do things that affect... like the current success that you have. But I think this is another very, very important thing that I'm constantly reminding to myself. There's kind of this other recurring theme that I'm noticing of just like thinking big.

and taking leaps and i love this point you made of not doing that is actually a big risk not taking risk is a big risk that's a really powerful point and it's innately scary to do something risky and so i love the push here of just like take more risks because it's so easy. And this comes back again to the beginning of the conversation where you were just like building things the way they've always been built and looking back and like, what have we even done?

What have we done over this year of hard work and tons of features? I think a lot of companies get in that place where they're just like, what are we like at Airbnb? I had this exact Brian's constant. Like, what are we even shipping all these billions of experiments that are moving the numbers? Like, what are we even doing?

like i don't know anything that we ship that's really exciting and so i think this is a really good reminder and push to just like think bigger and take and you need to take big leaps um so love that is there uh any other big counterintuitive lessons before we move in a different direction I really believe that many times, spending more time working on something will not yield to better results or to better products.

And, you know, I think that many times, like we, as people that are building products for others. get to a point where the feedback that we want to get in the bottom of our heart, you know, is like, wow, what an amazing product you have built. And I think this is a very bad feedback to get. for initial things that you are doing because it means that You know, I feel that in many ways, the point in which Real people use your product is really scary because you...

You suddenly, you know, put your work out there. And then in order to like actually, and you're afraid that you say, listen, it's a lousy product. It's not a good product. But actually, we really encourage people. to get really fast to production, to put traps for themselves that is caught by time and not by effort. And, you know, many times I saw that more time creates... More questions. It creates more complications. It creates more assumptions that we put for ourselves.

in thinking what our users need, and we invent things, you know. And we do it all from good reasons. We want people to like what we build. We want them to get value. But for me, like, this is a very important point that... many times, many times using like the setting traps mechanism of saying listen

We have three weeks. Let's think about it. And scope it by time. It makes you extremely focused. And, you know, this is very important because, you know... to get feedback from customers that say yeah listen this is on the direction I'm still missing this and this and this and also we really love the fact of this is not a good product.

And I can give you a recent example, you know, even when now we, you know, we work with big customers and of course, like there are different ways to implement what I said. then you are a small startup, but we are building like a new offering of enterprise work management. Think about it like a way of managing projects at a huge, huge scale, you know, thousands of projects, like tens of thousands of employees and so on.

I really love using the deadline prep and it makes you focused. It makes you sharper and thinking. And we just had a recent example with the offering I was telling you about of like enterprise work management, managing projects at scale. And you know, this is an enterprise product.

So you have all the reasons in the world to say, no, I can't release it yet. I need more time. I need to do more things. They won't use it. They need this and this and this. And I think that we actually released the first like alpha version to them. And we got a feedback of, listen, guys, this is premature. We need more like... more comprehensive value, but we got exactly the feedback of what.

And this is priceless. And my response to the teams is well done. Like I think you did an amazing job in like releasing it and making sure because, you know, many times. Being so afraid of releasing it and like thinking if I just have one, two, three more weeks, I will be the body product. I think it's not true.

This is such good advice. It resonates so much with recent other conversations I've had. So just to clarify what you're saying, basically you have a time box. When you say traps, it's basically a set amount of time. We're going to spend three weeks on this feature. And if it doesn't, if we don't hit the three weeks, we just cut scope, essentially. Is that the idea? I think it's like this is the basic version of it. But now for us, we really want and we really love.

doing it as an exercise for ourselves. For instance, let's say now as a public company, we say, listen, we're working on something, we want to announce it on the next earning. And put a trap for ourselves. Why? Because again, it makes you... It makes you super focused about things. And, you know, I think that in many ways. This results in a much better product because you are not building things that you invented. You are staying really true to what your users...

the real, you know, core of the value. And it's really funny to see the dynamics of teams, you know, when they are planning, you know, from the bottom up. It starts like, you know, with something that like, let's say you've done everything great. Okay. You have the opportunity, you understand, you have the KPIs, everything is in place, but now you're starting to plan it. And suddenly people are raising, you know, concerns and issues. And it becomes a sport to say what can go wrong.

and like being fear driven and then you tend to you know protect yourself and adding more content and more content and then when you see what happens it's actually like it's going to be shipped in two years Let me see. Okay, no. Okay. We have earnings in two months. What can we ship to these earnings? And let's put a tab. And then you suddenly see the conversation changes. First of all, it makes everyone really focused on what's the core of the value.

And it removes all the theoretical discussions that people have and things like that. And, you know, the result... are amazing and you need to remember when you do it you need to continue afterwards if you like according to feedbacks and and not let it go just but what you did in the first version but in many ways i really love the fact that you know the first version get a feedback which is not everything is perfect because if this is the the feedback it means that we build

too much and probably it's not focused product enough and when you build a lot of features this can be like you know the death by a thousand cuts because in each corner of the product you add more than you need Yeah, there's so much here that connects to the other conversation we just had. We had Gaurav Misra, he's CEO of Captions, and he made this point that if people aren't complaining about your...

You want to see people complaining because that means they care. Like there's something there that they care about. If you're not hearing any complaints, they could care less about what you're building. And that's a bad sign. I really loved it. Yeah. Their company actually goes to the extreme of what you're describing. Every engineer ships a feature, a marketable feature every week.

That's their pace. I really connected to it. And by the way, about user feedback, I think, you know, it's really nice because like... Many times, you know, people associate like... They only measure themselves by user feedback. the specific point. And I think this is also maybe, you know, something that is counterintuitive. Not every customer feedback is the feedback that will drive you to the, you know, to the end result of the best product out there.

There are many aspects to it. I can share just one example about us. We, as you know, in the beginning of the company, we, for instance, didn't want to have a free trial. And part of it... is that we really wanted to hear feedback about our product only from people that... The product means something to them. The best proxy for that is that they are paying because it means they get real value. And, you know, in that sense, it helps us. It helped us at the beginning to stay.

super focused about like, you know, separating the wheat from the shaft with the customer's feedback. So I think it's a super important point and we need to take customer feedback in context. The other really interesting point here that you're making is this idea of, we had, I think I mentioned this already, Ryan Singer, he's the creator of this method shape up.

which is very centered around appetites over deadlines. There's so much like so many, everyone listening to this has probably gone through an exercise where like, let's redo our landing page. And it's like, yeah, it'll probably have some impact. Let's spend some time on this. It ends up taking like six months.

And everyone's like, why did we spend six months redoing this freaking landing page? Like, look, I would have given it three weeks and then moved on. And the way to do that is you just commit up front. We will spend three weeks on this. We'll get as much done as we can in three weeks and then we'll move on. People talk about this very hard to actually do. So I love that's how you actually approach some of these bigger features you work on.

Do you guys practice shape-up by any chance, or is this just like a thing you do? No, actually, I wasn't that familiar with it, but I'm definitely going to check it out. Okay, cool. Yeah, it's a whole method. And we'll have I think the episode right before this is actually that episode. OK, let me go in a different direction and kind of keep extracting lessons from this journey because that was a really fruitful.

place to go. So let me ask you this question. What's one thing that you wish you'd known before stepping into the role you're in today? This is an interesting question. I think there are many aspects to it. Maybe if I'll take the personal aspect. So, you know, I've been in charge of like the product and technology from like since I joined the company, but. With that, my role has changed, I think, like dozens of times. Like I feel I'm very fortunate to work.

in one company but actually work in dozens of different companies think about the scale that we talked about like each point is a different it's actually a different company and a different role and different challenge and I think that, you know, something that maybe is counterintuitive personally for me was that.

In many of the phases that we undergoed with, I felt that what got me to this phase is not necessarily what's going to make me successful in the next phase. And if I want to be even more blunt, you know. There were, like, personally times when suddenly I saw how my biggest, you know, strength, for instance, like...

mastering all the details and having everything in my head, knowing exactly what's happening on every corner of what we do. This was probably something that gave a lot of value when we were small. But as we got bigger, I think like it suddenly created, you know, even the damage, you know, continue to do the same thing. In many ways, it takes time to do this realization. And I think that a good advice that I would love to have is that...

Don't be afraid again to let go of things that you think are superpowers. Many times your superpowers that brought you to this point and made you successful. Many times you think that if you let it go, you won't be successful. And it's frightening. You need to constantly evaluate what your current role

is actually what is the role and what is needed in order to be successful in it and not continue with the inertia. And this is something that... i wish someone has told me yeah it took me time in many cases you know many cases i did it too late Is there anything that helped you realize this or get good at this? Is it like coaching? Is it just doing it and surviving and failing and be like, oh, I see.

I think all of the above. I think that one sign for that for me was... that in many cases I felt I'm doing a very good job. But then people, like, it can be like, I'll give you an example, okay? Like, for instance, doing a company like leadership QBRs, okay, quarterly business reviews. When we just started with it very early, you know, I would...

actually tell about everything. And you know, I remember one meeting that I went out of the meeting and I say, wow, I really managed to, you know, convey... everything and explain everything in a very articulated way. And like one of my colleagues in the core leadership team said, I didn't understand anything. Like, what is the bottom line of all of this? And, you know, it was like...

You suddenly realize that what you thought is good is not necessarily what the other people need from you at this point. And, you know, like after understanding that, I went and asked, like, what would be beneficial for you? He said, listen, I want to keep in my head like the three most meaningful things that you are currently facing with. I don't want to heal everything.

Like it's hard, but this was the point for me that I realized that I need to change and I need to change something. And like the requirements are different. Like at the beginning, you know, I tried to say, but listen, it's important that you know, like you're sticking to it, right? But we need to let it go sometimes and think like from the beginning.

There's this phrase that someone shared on this podcast once where as you rise in your career, you often go from the person that is pitching leaders on something to the person being pitched. And that's a really weird place to move from, you know, having to learn how to be, give great feedback, delegate, let go of things. And I love that this is a good example of that.

Since we're getting a little vulnerable and open about stuff, I want to try this question. You've done a lot of podcasts. You've done a lot of interviews. You've been all over the place. Is there anything you haven't shared anywhere else that might be helpful to share here about the journey you've been on?

Yeah, so maybe continuing with the same point, you know, like it's a crazy journey and it's crazy personal journey. If you think about it, like... I remember Roy once said, if someone would have interviewed me to a public company worth, you know, like I would say $10 billion in market cap and managing 2,500 employees. I'm not sure that I would interview myself and get myself to the job. And I can, you know, for me, there were a lot of moments and it's constantly happening.

you know, are going sideways and things doesn't work. And you see so many things are breaking down and, you know, you can be on the same day, super happy and suddenly... on the lowest point there is. And I can show, you know, many times I've asked myself like whether I'm the right person to lead it, whether we need like someone that is coming with all the experience to this phase.

And I remember like a talk that I had with Ferran, he told me something, listen, first of all, as the one who built it, no one would be able to do it like you. And I think it's an important thing to remember when times are tough. I really believe that, you know... If you have the passion and if you have the will. And if you are willing to do the hard work in order to constantly adjust and evolve and...

you know, to be vulnerable and also, you know, to say about yourself, like, I didn't understand something. Now I need to learn it and I need to do things differently. You know, it's a very important point if you want to do this kind of journey. And it's hard. And something I can share, you know, I can reassure everyone that are listening to us, you know, if you're feeling good. You're not the only one. Everyone is feeling it for once in a while. Be confident about yourself.

be vulnerable in order to learn and to evolve. And I really love to do like a mental, you know, mental exercise of like saying, like we said about the product. So let's say... I'm the nail of like next six months.

on these six months and what do i want to say about myself that i learned that i evolved and this helped you get out from the state of like everything is okay i'm good and it makes you like want to learn and want to evolve and also like I don't believe in like I think the one thing that really characterized me is that I can be like very you know it can be very difficult and very challenging time. I'm already bouncing back with energy and in order to come and do things and win it.

And, you know, there are a lot of things that we as leaders need to do in order to help ourselves to keep like this mental, you know, state. So I like to run. I like to do things that are unrelated to work in order to get back to my... But then quickly bounce back and to really believe in myself, in the team around me. So this is something maybe very personal, but... I'm pretty sure I'm not the only one, you know, feeling it. I appreciate you sharing that.

There's a post that I did a long time ago with a coach and she it was about imposter syndrome. And she made this really powerful point that like you are actually an imposter in the role you're in. You've never done this before. Like most people are imposters in their role. They've never been a chief product officer in a lot of cases. They've never led teams this large. And first of all, just realize that you actually are. And second of all, that's okay. And most people are, like you said.

And then third of all, this advice you shared about how to work through that is really powerful. Just like know how many people feel this way. Work hard, I think is a really important part of this. Just like know there's another day and that you can bounce back. Remember that everyone are people. No one is born to be like in the world that is currently at.

And, you know, another thing that, you know, in Monday we are scaling so fast. So even people that are coming with experience and I had, you know, the chance to see it over and over again. Because we are going so fast, each one of us will get to a point which is the first time he is doing it.

So experience matters. And we have like a lot of people that are coming and bringing experience from the outside. But also remember that and remember that everyone are people and like no one was born in a position. Yeah, and a company like yours, people have described it as like every six months you have a new job. Exactly, exactly.

We had Sheryl Sandberg once did a talk that I was at where people are complaining. We're just like so much is changing. We're growing. The culture is not as strong as it was. And there's just like things not working. Our processes are not. Hiring is hard. This is the problems you want because you're growing very fast and that's very good versus if you were not growing, it'd be much more painful and hard. So be thankful. This is the problems you're facing. I couldn't agree more.

You talked about things breaking along the way and things you have to deal with. Is there an example of something? I love these stories of just like maybe a moment of crisis along the journey where you thought like, OK, things are going to fall apart. This is over. See you, everyone. Yeah, to be honest, we have so many. But again, this is the problems that you are lucky to have.

But yeah, maybe I'll give you an example. Like, you know, I remember this day that someone from our customer success team has approached me and say, we have a spike in performance issues in the board. And, you know, again, like our boards is this table of like, think about it, like of data.

On each time where we add new functionality and we make the platform more mature, people are taking it to the extreme. So if you look back eight years ago, so these kind of tables usually had like, let's say five columns and 100 rows. And if you look about it today, it's like hundreds of columns, you know, tens of thousands of rows. And like, so performance was always a challenge and struggle, like in making sure that everything works.

smoothly and this is also a value to us. We really believe that performance is the number one feature that makes people use your system. So, you know, he came to me, and I remember that, like, suddenly seeing the spike in the ticket. you know it's super hard right like you say wow it's something super hard you don't necessarily have a magic wand of like fixing it immediately and what we did we actually again connected everyone to it the first thing i did was like

taking this graph to everyone in the team and showing and thinking together what we can do. And we did a lot of things and we worked really hard and we managed to make this situation better. And, you know, and then... time passed by and you are like continuing and then it happened again and i can share that on the first time on the third time in a different way. Back in the days, this is where I think many of our core long-term projects have born.

The signature one would be MondayDB. It's a name we use for an underlying data infrastructure that we've been building in the last three years or so. So think about a very small team and a very small startup. I remember the day that we said, listen, we need a few of our most talented people. They are now not going to contribute features anymore. We are putting them on a separate place. And let's think and solve this problem.

while thinking about 100x. And you know, it really, like in many ways, so different from what we talked about in so many other of the examples, right? And I think... Now we said, listen, instead of being like fixing an issue, we want this to be our competitive edge. We have a very unique product architecture where everyone can build their own schemas of the table. And, you know, it's like...

a crazy thing in terms of technology behind it. We want to do something that will not only solve the problem, but also will serve us as a competitive edge. And we took a huge risk because, you know, we took a lot of people and put them aside for that or like not a lot of people, but very talented people. And I think...

In retrospect, by the way, we released Monday DB, I think, one and a half years ago, like the first version. It did a huge, huge change to our customers. And in many ways, this is what actually makes us today a platform which is enterprise-grade. So my lesson from that is that if you feel about something, it is strategic. You need to not only solve problems, but be super proactive. And also, again, like...

This contradicts the fact of like, what are the goals? What are we going to achieve? Because you need to lean on like something which is strategic. So with everything that we said at the beginning of the conversation, there is also things that you need to do because this is the company you want to build. This is the product that you want to build.

And you don't necessarily get the, you know, looks of getting conviction from things that happened in the past or from data. You need to just go with your intuition and take this risk. And I'm super happy that we did it. Yeah. But this is an example where things really broke, you know, and what we did with it. There's a couple other stories of crisis I've been thinking back to, and there all seem to be a database.

started reaching capacity and we were about to fall apart because their growth was too fast. So that's an interesting lesson for people to hear, just like try to anticipate this a little more. And it sounds like that's what you realize is like, let's think 100x from now, not just like a couple of years from now. It reminds me of Brian Johnson.

dude that's trying to live forever or as long as he can. And he makes this really interesting point that I promise connects to what you're talking about, which is he's like, okay, what is your goal? He asks everyone, what's your life goal? And so they're like, oh, I want to do this and this and that. Okay. To accomplish that, the base goal you're not even thinking about is you need to not die. And that's actually the number one goal everyone should have. Don't die.

And I feel like that's infrastructure in companies. It's like you have all these metrics and goals, but really the goal underneath that is your infrastructure needs to scale. So it makes sense why this is outside of like, okay, we have all these metrics and goals. Not necessarily treating it as a tax.

or as a risk, but rather like, you know, for our offering, like as a platform, this is like actually now one of our core advantages. So it's super important as well that value to customers comes in different ways, shapes and forms and you need to... to think about the experience and not only about like, you know. And many times the general experience starts with... things that are reliable, performant, that you can count on them. And suddenly you even use them differently because they are fast.

I think this is another important aspect to it. That's such a good point. When you have a problem, something that's slowing you down or might crumble the company, just not flipping it for a minute, we just... put the bandaid here. It's how do we turn this into a strategic advantage if we really invest the time? I like that a lot. Okay, to start to close out our conversation, I'm going to take us to AI Corner, which is a recurring segment I tried to get to more and more with this podcast.

And the question is, what's an example of you using AI tools in your day-to-day work to do better work, to do faster work that you think might be helpful to other folks? And maybe I start with a personal one, you know, like I'm, it's not, it's not about work, but I think it really shows that for me, it was like a moment of like. really saying this has so much potential in it. So I actually prepared myself for a marathon and unfortunately I got injured in my knee.

So, yeah. So I went to do an MRI scan and I finished the scan and they gave me this disc with the results. And then they said, listen, you need to schedule a doctor appointment five days from now. Okay, I said I took it, put it in ChatGPT and asked for the results, an explanation of line by line, what does it mean? And then I, of course, went to the doctor and said, these are the results. But I think, like, for me, you know, this is something that I was really happy about using it.

And it also opens my mind a lot because I think that if you think about it from the product perspective, and this is how we think about AI in Monday, the technology is amazing. You can do so much with it. you know, they're still the part of like productizing it because every person that I talked with him about this example, like with enthusiasm, he said, how did you think about putting your MRI there? And I said, I don't know, like I just did, but...

This is all like creating products that actually allow people to leverage this technology. And more on the work side, you know, I use it a lot. I think like... For me, one recent example, I would say, is we really worked hard towards determining the pricing for AI offering that I was mentioning earlier. Just in like two hours, I managed to get the full perspective on what everyone else are doing, you know, and...

We have analysts and we have product managers, but the fact that I was independent and managed to get the initial thoughts and all the information in just a bit, it was mind-blowing. So I use it a lot in order to understand. things that are like very extensive, like what the competitors are doing, what is the history of this and that. And I think it helped me a lot in that sense. These are awesome examples. And is this all ChatJPT? Is that the tool of choice? And...

You know, it's hard. I have like my own periods right now. It's changing from one week to another. These two actually were with ChatGPD. Very cool. The first example my wife does all the time, my mother-in-law was in the hospital, and we were waiting for the doctor to show up, and she just put the chart in Chachibutin. It's like, what?

with the problem and it's exactly what he told us and it feels like like it feels like we're in a world now where an engineer without say cursor or one of these tools is just not Like that's not that's not possible anymore. And it feels like now with going to doctors, it's like if you don't do this and see what it says, like you're missing out on a big gap. There's this New York Times story. I don't know if you've seen where they actually compared.

a doctor's analysis versus a doctor plus JAT-GPT plus And guess what was the best, most accurate diagnosis? Yeah, I want to say CHGPT, you know, but... That's exactly what it was. Not even a doctor with CHGPT. You know, I'll tell you a story about it. So in the MRI, you know, I did it because I wanted to go skiing and I didn't know if I can do it or not.

So I asked Chad GPT and he said like all the recommendations and what I need to do and so on. And then when I was at the doctor, I said, I asked him the same question. Can I do ski? He said, I don't know. I never ski.

So it's not only about getting the information straight away and getting accuracy. It's the fact that you can continue a deep dive with it. And this is something that also like... when i was in the pricing you know it's not only the bit of information but the fact that you can continue and continue and continue it's like

It's definitely super, super impressive. And it doesn't get annoyed. It doesn't get bored. And it's very supportive. Yeah, it's always with good intents. Or not, but yeah. So kind. Amazing. Okay. Well, Daniel, we've covered a lot of ground. This was extremely fun. Before we get to our very exciting lightning round, is there anything else that you wanted to share or any other nuggets of wisdom you want to leave listeners with?

I think that in many ways, like the things that we managed to achieve in Monday is due to the great people and culture that we have. And, you know, on early days...

We used to take it for granted in a way that not the people, but the culture, the fact that everyone understands it, the fact that everyone is practicing it. And then you say, okay, culture is like something that you can't put your... fingers on but now as we scale like i really see how this is what actually drives everything forward yeah so

Maybe just to say like on a personal note that a huge part of how I see my role is about like the people and also about how we work together and what kind of an environment we want to build to ourselves. And we talked a lot about it during the episode, but, you know, I really feel that I can't underestimate on how meaningful it is and how grateful I am that I'm working with such talented people and doing what I love.

That's awesome. I bet we could do a whole other episode on just culture and what you've learned building a culture with the culture is like at Monday. But we got to we got to get to our very exciting lightning round. Daniel, are you ready? I'm ready. All right, so I've got five questions for you. First question is, what are two or three books that you find yourself recommending most to other people? The first one I would say is like... is the No Rules Rules A book by Netflix.

Back in the days, we used even the slides, but I think we took a lot of inspiration out of it. And I think that although we have different cultures, many of the things around like, you know, execution. and like excellent people and so on things that like I can really resonate with and this is something that we really like to give people away after talking about our culture and so on to get inspiration also from other cultures. And another, maybe on a different way, you know, aspect.

It's a book that actually Roy, our core CEO, is giving to me. Its name is Nonviolent Communication. And it's about... effective ways of communication and understanding the people and their needs and how to communicate in a way that actually promotes, you know, an effective communication. And what I liked about this book is, you know, mainly we love to talk a lot and like...

After we both read the book, like our way of talking like changed. So it's very practical. So I also like to give it away to our leadership and people within the team because they think it has like real value in it. I'm trying to remember the framework of nonviolent communication is like, I observed you. that's speaking too much in this meeting and that made me feel

Like I wasn't listened to something like that. Right. I forget. You shouldn't be judgmental. You just need to say facts and talk about how you feel like in that. So, yeah. Yeah. And I know I'm kind of joking about it, but it's actually really powerful. We had a Carol Robin on the podcast who. created this program at Stanford called Tachifili, which is similar to this whole process, this whole approach to talking. And by the way, I love the combination of Israeli directness.

And non-violent communication, I want to see that in action. Yeah, definitely. Okay, next question. Do you have a favorite recent movie or TV show that you really enjoyed? So to be honest, I don't watch TV so much. I get bored really fast and going back to other things. But like when I do watch TV, so many times it's like in order to clear my head. So it's not that kind of exciting thing.

Maybe a different thing that I'm doing is like playing on the PlayStation with my son, you know, FIFA, just to vent out. Yeah, and in terms of serious, maybe like... One thing that pops up is like the formula. I really liked it. Formula One. Try to survive. Drive to survive, exactly. I really love seeing the dynamics and everything behind, you know, it looks like something simple of like driving cars, but you see that there's so much into it.

And so it's also something that like really interesting and like opens your mind. Yeah, I haven't started the new season yet. I wonder if it's great. Yeah, likewise, yeah. Okay, next question. Do you have a favorite product you've recently discovered that you're... So, you know, I don't want to fall into all the AI trap, you know, in terms of products. So maybe I'll say something which is not so recent, but a product that I love.

I really like to take pictures. And one product that I really love is Google Photos. I think that, you know... They managed to create something which takes the technology edge, but to a place where myself as a human really can connect to it and get a lot of value for it. So I'm a really heavy user of that.

Yeah, that is a magical product that I think people underappreciate. Yeah. Next question. Do you have a favorite life motto that you often come back to, find useful and work your own life? Stay positive. Being positive, sing and... It's a huge huge power and it's a huge driver.

And it allows you to give energy to the people around you. And it's contagious. So I really love, you know, staying positive, making sure that we keep being optimistic. And it doesn't mean that you need to... you know, let go of the problems and don't see the problems, but also think about Always look forward and always think how you can take the current situation and make it better. And I learned with the way that it's really more fun and actually brings better results this way.

I'm 1000% aligned with that. Final question. I know you were in the army at one point in your life. Is there anything that you learned from that experience that helps you build better product? The funny thing is, is that I think that Many things that I did in the army, I was actually commanding. a very big group of people in the army. And I think it's not about building products, but more about building teams and building this sense of purpose, sense of shared belonging.

And I think that in that way, many things are quite similar. It might be like counterintuitive, but many things are quite similar. from that many many of the things of like being together although it's like a hierarchical environment It's something that I take with me and a lot of practical ways to...

Daniel, this was awesome. You're awesome. So much stuff that we went through, so many golden nuggets. I think that we're going to help a lot of people with building products, building teams, scaling, surviving all these scaling challenges that keep coming up in these conversations. Two final questions. Where can folks find you online if they want to reach out? Maybe talk about being more transparent. And then how can listeners be useful to you? So online, like I think that...

Two main ways is like by LinkedIn, I would say. Second is podcasts and like I'm guesting in a lot of podcasts and I think that this is like a cool way to share things for stories and for like practical examples. and you know in terms of listeners being useful to me so First of all, in many ways, they already are useful to me. I really love your podcast and I'm getting a lot of insights from others and this is something I really love.

So many of people that probably listening will also contributing to that. So thank you for that. And I really hope with that, that this episode would also be meaningful to people and that they will take value out of it. And if they are, it would be amazing to hear about it. Like I remember, you know, someone that sent me. a picture of his new dashboard in the office and what he do with that and add additional ideas of what you can do that we actually took also here on Monday.

If you do something, even if it's small, let me know. It's super fun to hear and also interesting. All right, there's the call to action. If you implement some of Daniel's advice, especially put up new dashboards or monitors in your office, please send photos over LinkedIn, it sounds like is the best medium. Daniel, thank you so much for being here. Thank you very much, Lenny. It was a pleasure. Bye, everyone.

Thank you so much for listening. If you found this valuable you can subscribe to the show on Apple Podcasts, Spotify or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenny's Podcast dot com. See you in the next episode.

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