Healthy Tension: GTM & Product/Eng Collaboration at Hundreds of Millions ARR Scale w/ Tido Carriero & Joe Morrissey #172

I had been at segment for four years and the big unlock for me and I think what I needed to lean into more in retrospect from a trust perspective was that Joe was really going to be a different kind of go-to-market partner where we had zoomed way out. We had looked at a multi-year strategy, not just a list of 25 features and ordering them quarter by quarter by quarter. You've got to go through this tension and I think one of the things that can happen is you avoid the tension, you avoid the conflict. You say yes to things that maybe you're not comfortable with both on the product

and on the go-to-market side, then the plan goes wrong. So I really think the tension is the critical thing and the struggle is the critical thing and that's where the learning is. Hello and welcome to The Engineering Leadership Podcast brought to you by ELC, the Engineering Leadership Community. I'm Jerry Lee, founder of ELC.

This episode features a session from ELC annual 2023 and this conversation tackles the dilemma of finding a healthy tension between go-to-market, product and engineering collaboration at the scale of hundreds of millions of dollars ARR.

In joining us we have Tito Carriero, co-founder at Koala and former VP of engineering at segment and Joe Morrissey, general partner at A16C and former Chief Revenue Officer at segment. Tito and Joe share stories of their first cross functional annual planning meeting. They get into the world of the world.

They get into the frameworks for annual planning sessions to help you develop value drivers for your organization. They talk about how to build a healthy trusting relationship between product and engineering when it comes to building and executing a successful go-to-market strategy and more. Let me introduce you to Tito and Joe. Prior to Koala, Tito led the product and engineering team at segment from $5 million in ARR to its $3.2 billion acquisition by Twilio.

Joe is a general partner on the growth investing team at injuries and horwits, focused on enterprise technology companies. As Chief Revenue Officer at segment, he scaled revenues to upwards of $200 million dollars ARR in advance of its acquisition. Enjoy this conversation with Tito, Carriero and Joe Morrissey.

Thank you. We're excited to be here. Joe and I worked at the hip for several years at segment and we don't get to work together as much anymore, so stoked to be chatting with you today. Before I hop in to my part of the story, maybe I'll ask Joe a question.

Joe, what were your first impressions of me? Feel free to tell some of the lower moments at the beginning of our relationship. Thanks Tito. No, actually, I really liked you. I was super impressed. First time I met you was in the interview process and for me, you were one of the big reasons I joined the company.

I went to the company and it all went downhill from there. I'm going to get it. I thought, this is going to be a great engineering partner to work with. He really gets it. When I joined the company, you and I had a meeting and I went around interviewing all of the executives to get feedback about where they thought the company, the product sales team was at and what we needed to do.

And your feedback to me was, look, this product is great. The problem is the sales team. The sales team don't know how to sell the product. Now, they could do it when we were small because when we were small, we could put every single sales person through product training and make them experts at product and then they just went out and sold.

And now that we're big, we can't do that anymore. So my advice to you is put everybody through product training and immediately I thought, oh boy, this is going to be more difficult than I thought because I, you know, I fervently believed that sells people shouldn't be selling on product and features. They should be selling on value.

And we really didn't do that at segment. And I think that was one of the root causes of our challenges. And so, you know, as I went around and I interviewed some of the other executives, I heard similar things, but I also heard different things about what the product was. And I was totally confused. So at one of the first 18 meetings, I attended.

I asked everybody to write down the answers to three questions. What problems do we solve for our customers? How specifically do we solve them? And how do we do that differently or better than the competition? And then there were six people in the room. And when we went around the room to have everybody read out their answers, we got six different answers.

And I was like, OK, so it's the sales people's problem. They didn't have to sell the product. And what was clear to me was like, we had built a great product. We'd actually built lots of great products. On stage, I think we came to the realization that we had built too much. Right now, sales was partly to blame for that, I think, as we'll talk about later. But, you know, what was clear to me is like, we didn't have a focus on who to sell to, what to sell and what value to articulate around that.

And so, you know, that's what I said to work on doing in the first year was trying to drive some clarity around that. And I knew I would probably get one shot at this. And so I asked our CEO Peter to go all in on sales enablement. And I really kind of I wanted to use that as almost a vehicle for transforming the company in terms of clarity and focus.

And that's where you know, you did jump in and made massive contributions. And I think we started out having a really, really great relationship because we got really focused on what our value drivers were. And out of that process came I think a real clarity around, you know, what the core value of the product is.

What we should be building what we shouldn't be building who we should be selling to who we shouldn't be selling to. So I see P value drivers, all of those things. And you were, you were great partner to work with at that time.

So now maybe you can talk about the little point a little bit into Joe's tenure. We were tasked with doing annual planning together and our boss Peter was on paternity leave. And so he said, you guys just go figure it out. And I have this memory. I was sort of halfway on vacation in Tahoe, but trying to do annual planning. And I was so frustrated with Joe and what I felt like were these impossible set of priorities that I called Peter back from paternity leave.

So I was on the phone muting for long periods because I was crying because I was just like so frustrated. And I think that really was the low point for sure. And the beginning of what would be a beautiful relationship. And I think the key piece as I think about the story now years later was this alignment around value drivers and was not the most fun session we'd ever done. It was 48 hours basically locked in a room.

So maybe three or four of his top performing A E's, S C's, you know, people who really had had a lot of success selling to different verticals and segments. We had several folks from my team several of our longest 10 year PMs, all the co founders, most the exact team. And we just sat there and asked ourselves these incredibly simple questions, which in retrospect, how we made it to tens or low hundreds of millions in ARR before we had ever really asked ourselves these questions.

Blows my mind. We did somehow, but I think that clarity of like what the value was that we provide our customers what they are really paying for and what they care about was the threat that really started to unite us and started to bring us on the same page so that we could have a clear list of things to go after.

When I do think a big piece of that and a partnership I hadn't had on the go to market side was I finally had a partner who was really going to say we do these four things incredibly well. And if you are not one of these four things, it's actually revenue that we're going to say no to. And so once I realized that I could really rely on Joe to also hold the team accountable to the boundaries we set together, that started to unlock quite a bit of alignment and things we could go tackle.

So maybe I'll let Joe tell a little bit of the story of the annual planning process and what we agreed on if that sounds good. Sure. You know, today I feel really terrible about that whole time. And you know, I remember I went at you really, really hard. I kind of the back story was it was during COVID. My family were back in Europe long story. I had to go back to Europe with them.

So I was working California hours from Europe at night and totally exhausted. I know Tito was burning the middle night. I also really exhausted. But we had a huge number to do the next year. Almost all of it was coming from sales capacity. I knew we're going to have to hire a lot of people. It seemed like an impossible hill to climb.

And historically segments growth had come from us building new things, launching new products. Before I arrived, the company was like launching products all the time and had a tremendous product velocity. It was doubling. And now all of a sudden we weren't able to build anything anymore for my entire time there. Like we hadn't launched a new product. And a lot of what we had wasn't quite working. Right.

And I know that Tito was with snowed under as well. So as we started going through the annual planning process, I think Tito, you sent me a list of 25 things that you could build in the next year. And you asked me to rank them one to 25. And I was like, oh boy, have I have I done nothing right over the last year.

And as much in all as I look through the list of things, I kept a compliance in a cloud-prem solution that our customers were really, really clamoring for. Like there's no way we will build any of this. And so I went back to you and I said, look, just do three things. Okay. The three things I want you to do are one, let's get product quality nailed down.

Right. Two, let's make the platform extensible. Right. And that was really, really important because we had to build up professional services. We had partners who could do things themselves if we had made the platform more extensible. And that would mean that there would be less lift on the engineering organization. The engineering organization would then be able to build more product later.

But if we didn't do this, we would never get ahead of the ball. Right. And then the third thing that I wanted was multi-region support because a big part of the number that I had to deliver the next year was international, international expansion. And without it without multi-region support, you know, all the people I had hired and all the investments we had made in the mea and APAC, we would just have to let those people go.

And I didn't see any other way to make the number up. And so I felt like pretty happy about myself going, you know, aren't I a good guy? I've just said no to 25 things and I and I stayed up to build anything new. And instead he started putting you started pushing back on all of those things eventually. And I was like so frustrated. I felt like I can't make this number.

You know, the partnership is just not working, but maybe you can expand a little bit of what I felt like for you. Yeah, I had always had in the back of my mind this spare capacity of like 40, 50% for customer emergencies. And so I was still sort of operating under that capacity assumption that there was just going to be all of these customer emergencies where like someone had sold slightly outside of the lines.

And so for me, it was really hard to believe this new world, which Joe did indeed deliver on that we were actually going to really stay within the envelope of the value drivers that we had created together. And so my capacity struggle was adjusting to this new world view that we weren't, you know, just I had been at segment for four years in every history of all four years had been, you know, 40-ish percent of capacity kind of going to solve these little emergencies here and there.

Which are often were feature ads that no one had ever really said we did, but the marketing materials kind of said it. And it was a reasonable assumption that we did it based on where we were with the contract. And so the big unlock for me and I think what I needed to lean into more in retrospect from a trust perspective was that Joe was really going to be a different kind of go to market partner where we had zoomed way out.

We had looked at a multi year strategy, not just a list of 25 features and ordering them quarter by quarter by quarter. And we had really aligned that we can hit this plan together over the next 12 months and set us up for another good 12 months after that.

And so if we do these three foundational things and so a big piece of the puzzle for me was going back to the team and the team had been a custom of course to shipping several of these new features every year at least if not more often and several of these customer emergencies and saying like pretend we don't have to do any of that like really how fast can we do multi region for instance that was like the really big one.

We had had a very senior engineering team look at that very closely and the estimates had come back several times that it was like a 24 month project. And that was delivered in I think it was 13 months we gave ourselves a year plus one month and it was delivered on time to the day it's delivered shortly after I left the business but it was delivered on time.

And that was because we had freed up all of this other capacity and so for me I was just like wish I had taken that leap and realized like hey if I plan with my go to market leader for a year or two years in advance we can really hone in on the things that are most important and deliver much much faster than we've been accustomed to sort of delivering these things because we're so focused on the three things that matter.

The thing Joe brought to the table here was we're really going to tell customers if we do not do one of these things that we don't do it and we still would like them to be customers and you know here's an sc work around or here's what you can do on the platform and build it yourself or we can give you services to help fill in the gaps here but we weren't going to just sort of endlessly promise with a blank check that engineering will sort of help fill in the gaps which had been the reality I had been in for so long.

And so to have a leader that I could trust to really deliver on that took me a while to get used to and we were really a year into the partnership and this was our first annual plan but if I could go slap younger Tito I would and say like Joe is serious he's really going to keep things in the envelope and so you need to up your game in terms of how fast you deliver those three focus things that he wants maybe the craziest that for me was the platform focus we had basically been stalled at at about 300 350 integrations segment is like a great deal.

So I think that's the most important thing to do is to get the most of the questions segment is like a customer data platform that was very famous early days for having the most integrations I had been at the business for about three or four years before this and we had grown from about 250 integrations to 350 integrations when we launched that platform extensibility and then looked at the metrics about nine months after launch.

So I think I've grown the catalog in some sense from 300 integrations to 6000 integrations and that's because you know everyone is building their own integrations they were connecting is a lambda like environment and they were able to do all of these crazy use cases themselves but that was also to Joe's credit because like they were only able to do that because we had an incredible professional services team that was helping them.

having the right sales conversations about, hey, we'll do these 14 integrations you have really well. The rest, you need to eject to this other, you know, functions environment. And so you really are able to make like a lot more progress if you slow down a little bit and stop just like chasing like four integrations per quarter and build this thing correctly and then enable it on the good of market side as well. All right, that's the rest of my annual planning story.

Any other reflections before we start asking fraud and questions? Yeah, a couple actually. So just on that point, Peter later remarked that it was interesting that the best annual plan that we ever did, which came out of the struggle that you and I went through, was one that he was totally not involved in or there for, which kind of spoke to me of like the necessity of like the learning is always in the struggle, right?

And one of the things I think that you've got to go through this tension, you've got to embrace it and you've got to find a way to resolve it on both sides because out of that comes platform for driving growth. And I think one of the things that can happen is you avoid the tension, you avoid the conflict. You say yes to things that maybe you're not comfortable with both on the product and on the go to market side, then the plan goes wrong, right?

So I really think like the tension is the critical thing and the struggle is the critical thing and that's where the learning is. But I'm curious, Tito, now that you are founder and CEO of Quala, which is a great product, by the way, I encourage everybody here to check out getcuala.com, the shameless plug. You're leading Boat Engineering product and sales. What have you learned, now that you've crossed over to the dark side? Yes. So I have two technical co-founders.

So I'm primarily an AE right now. And I apologize for everything. I think my biggest learning is to get someone to the point, I just didn't realize this in segment, but to get someone to the point where they are so excited about your platform and they are ready to go. And there is one little rough edge that is preventing, it seems like a pretty minor thing in the grand scheme of things of the platform.

But it prevents their whole use case, how frustrating that is as a seller to not be able to really learn from what's going on in reality in the market. And you feel incredibly connected when you're having dozens of these conversations a week with customers. And so I wish I had realized what a valuable resource to go to market feedback was back at the time, because this truly is a megaphone that is blasting the message with 100 people or 200 people.

And they're also collecting all of this feedback about exactly what's going right and what's going wrong. I just don't think I had an appropriate appreciation for both how hard it is to get someone kind of on the brink of really committing to a large deal with you. And I wish I had done things a little differently in retrospect. But the other big piece is just how valuable that feedback is when it can be synthesized. Obviously, a platform can't be everything to everyone.

But that synthesis, those mechanisms for getting scaled feedback, I actually think the stuff we were getting from our sales engineering team, those were Joe's real product specialists, sales engineering team, CSM team, some of the best AEs, some of the best AEs in particular regions, some of the best AEs in particular segments. All of that stuff is just like A plus plus plus feedback. Over time, I've come almost to appreciate it more than what a PM is going and getting.

When I think about what a PM is doing, they're sort of randomly reaching out to three to eight people. And often, these go-to-market experts have spent 100 calls in the last quarter or two and just have a lot more breadth. And sometimes even depth than what a PM team can go do. So a lot more appreciation, a lot more hunger for all of that feedback. And I'm in the MVBOL spot at Koala, where I'm also the PM.

So I can immediately go from AELAND to product roadmap, which I guess is a good spot to be in as a seller. But yeah, it's been definitely different and incredibly fun. And yeah, just a lot harder in all of the ways to line up a deal.

So if you are sitting across the table from a good a market friend, have some empathy about what they are doing and consider building that little thing or maybe helping them with a workaround often is actually not a hardcore platform feature needed, but it's a little bit of creativity on the enablement. And that is just as good for the customer. I think those are my reflections. Cool, should we open it up for audience questions?

Thank you for the inspiring story, the struggles, and everything you shared. You're welcome. I think you guys went from a lot of chaos to a lot of clarity in how you described the 25 items and then getting it down to the top three. What kind of exercise or annual planning or rhythm did you use or do you usually use to get to those value drivers that you talked about? I'm going to let Joe handle this. It was actually probably more of the sales enablement exercise we did.

That was really the core of it that we did well in advance of annual planning and Joe can explain the magic. Yeah, so we use an external firm to help us build this. I think that's always valuable because they don't have a dog in the fight and they can help facilitate.

And what's super important here is you've got to bring the founders, you've got to bring the heads of product, you've got to bring head marketing, head of sales, you've got to bring all of the executives in around the table and they've got to be committed to that. And then you come up with a pretty deep discussion around what is it that we sell, what problems are we trying to solve, how do we solve them, and where have we done that? Because the customer feedback is super important.

And so once we went through that process, that fairly intense process about what our value drivers are. And for those that don't know what is a value driver, I should probably explain that. A value driver is the top of mind concern that your customer has, that your buyer has, that is on their mind whether you show up or not, whether you exist or not. And typically, all they're thinking about is how do I reduce cost or avoid cost? How do I avoid or mitigate risk? How do I grow revenue?

Or how do I accelerate time to value? Every value driver maps to one or more of those four concerns. And if you can't as a company articulate how your product can solve those problems for your customers, you're not going to resonate with your customers. And then what you may end up doing on the product and engineering side is just responding to very often, poor feedback from a go-to-market team, who tell you things like, I need you to build this feature to close this deal.

If you just do this thing for this customer, then we'll close this big deal and we'll make the quarter. I think you did that a few times, right? And then the next quarter comes along, and it's another customer with another thing. And before you know it, now you've built a bunch of custom products for lots of different companies. And your product roadmap is all over the place. And you find it very, very hard to focus and actually make progress on almost anything, right?

And then you end up supporting lots of custom deployments. If you get very clear to begin with around, you know, what is it we're going to solve? What types of customers then have those problems? And what will we say yes to? And what will we say no to? Then your product roadmap, I think, starts to evolve very clearly. But the customer feedback at every stage of this loop is super important.

And then where the sales leader has a big responsibility is they've got to enforce disciplines throughout the organization. They've got to stop the, you know, I need this feature for this deal to close type of hero behavior. If I sell this company that's outside of our ICP, then, you know, we'll be able to do a big deal there. You know, and it's really hard when your sales leader is saying no to that.

But if you do that and you have the courage to do that, then, you know, you build trust with the product team and then you can ask the product team to do things for you. That was my learnings from that experience. Yeah, I would just plus one how important the cross functional thing was just Joe was very insisting on day one that it was a CEO, all founders, all exec team, and top performers from both the good market and product org coming together for two days to do that.

And I just think there's so much information that sort of gets locked up when you're not having this free flowing conversation between all of these parties. So that was one key thing. I still remember the value drivers today. I mean, it ends up looking like a glossy battle card that every single rep can have available on a call. We do these three things, move fast with a modern stack was our first one. Personalized the customer experience was the second one.

We just were asking ourselves, like, is this a problem that this, you know, potential customer needs solved? If so, we need to make sure we're the best solution. And a lot of the things Joe was asking for actually weren't adding like a bunch of new value drivers. It was delivering better and cheaper and whatever on that, those current promises we had already made. And so that was really the clarity we needed.

I think the annual planning process that we actually ended up running was pretty similar to every other one we had run. But it was a couple months after we had just really deeply understood what it was people were using segment for today and what they wanted to be able to rely on it for at a bigger, more enterprise ready scale. And so it was pretty clear to us that all of the kind of annual planning needed to come back to this value.

And this is like the core of like where product meets go to market. It's kind of crazy to me. I was just saying to Joe and the way over here, it's kind of crazy to me that segment made it to like, you know, a hundred million in ARR-ish before we had ever really answered that question for ourselves. So I would think about doing that kind of exercise if you don't think that's crystal clear. And I think it'll make any other downstream planning much, much easier. Hi, I have two questions.

You know, I think it takes a lot of maturity and courage to say, okay, I'm gonna say yes to these, but no to everything else. That's not easy. I'm just curious. The external company come up with the three values, right? When you do the 40 hours meeting, they stay the same or did you completely change it or some change? Oh, we were writing them live in that 48 hour meeting. I mean, it was two days on site.

So we started with a blank template that said, you need to fill out two or three of these value drivers. We had a bunch of customer research and inputs and then also just people from the field. But we were actually sitting there with Google Docs open, like writing the value drivers. It was an interesting process. We wrote too much. All of them kind of got a little bit bland. We said, we need to really tighten this up and what's the essence of the things we're really trying to say?

And so it ended up being like a diverge, converge, diverge, converge type process. But yeah, it was like collaborative writing, talking about customers saying, like, does this fit? What these four customers are doing with us? I'm really trying to get to opinionated things that didn't just sound like the least common denominator pitch, but really something with specificity that we could like go make a PMM campaign against. We could think it was really a differentiator in a sales call.

And we could go to the product team and say, like, this may not fully work yet, but this is what we think people want from us. I think Joe had an interesting set of point though, which is, it really has nothing to do with your product, the value drivers exercise. You're explaining problems that exist in the world that your product happens to solve really well. And so that was one of the key things, because my head had always been like, what's the feature list?

And there's only one very tiny spot in that value drivers exercise that the product even makes it in. It's called required capabilities, but you need to describe the problem, the before consequences, what will be true about the business, if this problem is solved, i.e., more revenue or less cost or less risk or whatever. And it doesn't even come until, like, what's required to do it, where the product even shows up.

And so you're really talking more generically about problems and solutions in the world, which was like a, that was what the forced management, the firm we worked with, was really coaching us on. But they don't know the answers to these questions. It's like locked in the heads of your GoToMarket team. So it's truly collaborative. Yes. That's good to know.

And the other question that is just one thing I'm curious about, like, I work with different organization, and we have this org, the sales team doesn't get digging the product too much, and then have the sales engineer to do the demo, and not a team, the sales people do the demo themselves. So it's just wondering, Joe, which type, how deep do you think a sales person should go on the product? I think that depends a lot on the product and the business.

I've solved everything from very simple solutions to very complex ERP, but I generally think that actually the sales people are better off not doing demos and trying to step back and talk about business problems, and understand, try to get at what the customer's value drivers are, like Tito laid it out, before you ever talk about the product, you want to understand what is the pain of the company has, what's the impact on the company's performance on because of that pain?

What would the world look like if that pain was solved? You know, what would all the positive business outcomes be? Then like, what did the company think the required capabilities are to get there? And how are they going to measure success? So that's a lot. That's a lot to do discovery on. That's a lot to talk about. And only then should you talk about, here's how our product does it, here's how we do it, differently, a better than competition. And here's where we've done it before.

And so the more you can delay that point of talking about your own product and focus on the customer's pain, the more better you'll be able to sell, the more trust you'll build with your customer, and the more better positions you'll be able to win. Thank you for a great story. While annual operating plan or annual planning is a good forum to build that alignment, how did this change the day-to-day operations on the ground for the rest of the year? That's a really great question.

I think let me start on the sales side. So first of all, I really believe passionately that product and sales need to work in tandem hand and hand. And once we got this clarity on who we were, what we wanted to be when we grew up, and how we were able to sell. I think we started developing a multi-year road map for how the product should evolve.

And in any startup, I think that's so super critical, because one of the areas that segment got itself into trouble was it ended up going up market way before it was ready to do so. And I think we landed a bunch of enterprise deals really early on that were very big. And we then assumed, hey, we've got product market fit in the enterprise with these giant deals. But what we had was false signals. We had product market fit in a very, very small part of a huge market.

And it wasn't going to be for years until we could do things in the product, like the machine learning into it, build marketing automation, journey orchestration that we would truly be able to address the needs of the enterprise. And I've seen this happen at every company I've ever been at. So that was the first thing. I think we got really tight. And we both knew that we had a responsibility to evolve.

Both the product roadmap and the go-to-market motion in tandem, because it's not just about the product that you can deliver for your customers. It's also about how you sell that product, because you sell in the enterprise in a very different way to you sell in SMB. And in our case, our SMB customers, they didn't need any help mostly to get it implemented. But our enterprise customers, they were probably, we were probably part of a $100 million digital transformation project run by a center.

And so we needed to build professional services and an SI relationship, a whole bunch of different things. Just to be able to sell and make those customer successors as a first thing. The second thing I think day to day, we just got way more customer focused. I think both teams had been very inward looking previously. To Tito's credit, I'll give him all the credit for this. He drove a program called Lighthouse, which I'll let him talk about, because he'll do much better job than I did.

Lighthouse was, I don't know if it was my program, but between us and the customer success program team, we would, I think it was highlight either two or three customers that were either having trouble. Sometimes occasionally we do a positive one on like a huge expansion opportunity, but we would bring to a weekly meeting two or three customers.

The good market team would prepare an awesome, maybe 10-minute presentation of what's going well, context, and why I was purchased, what problems we were hired to solve, context on what the needs were, either from the product side. Sometimes the needs were actually more from the professional services side. Sometimes they needed an SC assigned to the account. It could be a lot of different things.

Sometimes there was a product manager working with the account team could bring to product leadership me, sales leadership Joe, support leadership, it's awesome guy named Steve DeVito, who Joe hired. And this was the chance to discuss like all of the most miserable and tough situations and things brought to Lighthouse program.

That was the way that if we did need to do a shift to product planning for the quarter or for the month or for the week or for the day, because some emergency was happening, we would funnel everything through Lighthouse.

And what I loved about it is it really got the account team to be thinking very critically and strategically about what the status was, why we really need this thing, and then it let all of leadership together, not in separate meetings where separate things are happening, analyze and commit to a solution. And so it wasn't that we had never deviated from those three annual planning things ever, ever, ever.

It was that the volume of those things was much, much, much less, and it was a much more ordered way to escalate these things and have a great discussion. And sometimes the great discussion is actually like, this is really not a product feature or area we think we should be investing in, but we think we can kind of get to where they need if we assign an SE sales engineer to the account and give them some free services for a month. And so sometimes that was the solution.

Sometimes it really was a platform bug, a platform feature, but it gave us a really nice place to have these discussions. So if you're not doing something like that today for your most challenging customers, your biggest upsell opportunities, I would highly recommend a program like that as the entry point for getting on the same page in a more like weekly tactical point of view. Hi, yeah, thank you.

But my question is when you decided on these three goals, like did you have to reorganize the organization to kind of align to delivering? How did you reorganize your team? And also how big was your team? Like how big was the company at that time? Yes. Yeah, great question. So I had a policy that I talked about with my team, which is we're going to do a reorg every February, because we're going to get the annual plan locked in by the end of January.

And like we're just going to not have perfect alignment. I would say my goal with those kinds of reorganizations were to try to touch as few manager report relationships as possible, because I wanted as much continuity for the engineering team and engineering leaders to have similar reporting structures. I would say on any given year, it was usually about maybe 10 to 20% of people would actually switch managers.

This year was probably a little bit higher, because it was a little bit more of a come to Jesus tectonic shift. But it probably wasn't higher than 30%. I don't remember the exact number of people whose manager changed. Yeah, the team was probably about to 300 at the time in terms of like end product design security. So yeah. And then sometimes it was like, we'll take this whole team and like give them just a slightly different roadmap and purpose.

And that was always the hardest thing, because you're kind of like canceling the thing that they were working on for a while and requires some finesse to explain why this other thing is even more important.

One of the things I found though is once people really understand the vision that Joe and I had forged for the next year or two and how this specific team connected to that value driver, which was so important for the two year future, people are pretty valuable and pretty excited to go work on that thing. And so again, I think all of this stems from the clarity that we established in this two day working session on like what is important, why is it important?

All of that same stuff was in the like Reorgcoms, it was in the all hands as we like announced what was shifting. And I think the team was actually accustomed enough to this happening each year in February that it also just became less and less impactful and worrisome for them. They just understand that we're growing startup, we're figuring out our priorities each year.

And it would be insane for us not to be oriented toward what our company is trying to do just because that's not what the team structure looks like. And so we got to a pretty healthy discourse about that. The last thing I'll say about once a year is like I was at another company where it felt like there was as soon as a Reorg ended, there was always another Reorg starting up. It's just like gives the boys a ton to talk about and worry about and think about.

I think just having a cadence, I think about once a year for like Series B through D is about the right time to revisit things. It helped prevent some of the distractions that I had experienced at other companies. So I would definitely suggest something along those lines. And not being afraid to do it is the other thing.

I mean, if the company has a strategy and the team is not supporting that strategy, you should not be spending $20, $30, $50 million a year on slightly wrong strategy because it's uncomfortable to re-orc. Took me a while to appreciate that, but I did get there eventually. Thanks, Altho, for the lovely discussion. So how much were the engineering leadership involved during your annual plan and at what points? Like to my understanding, it sounds like it was mostly between GTM and product.

Maybe a product played more of a bridge role, but how were the engineers involved? Yeah, engineers quite heavily involved. I mean, as we had those 25 things that we were thinking about, none of those made it across the line to Joe, even though it ended up being the direction we were going, we had engineering leadership heavily involved in sort of sizing all of those things, giving us like, you know, not an incredibly precise, but a rough swag of comparative sizes.

You know, as Joe and I were talking about those, and it became more clear that actually, these three key goals to support this like key value driver and this move into the enterprise was actually the thing. You know, before I committed to anything, it was like all of the engineering leaders needed to take a pretty good look and figure out exactly how long this was going to take. Their numbers came back a little bit longer than my own gut intuition was and what Joe really needed.

And so part of my role was like helping figure out ways to bridge the gap through reorganization or thinking about the problem differently or pushing on the end leaders to get a little bit more aggressive with the timing as needed. For us, it was really the multi-region.

The other two projects were pretty comfortable, but multi-region in the kind of time frame we were looking at, we had to basically come up with a lot of product simplifications, which was like not where the engineering team started in their head, but it turned out the good market team was totally fine with it. But I would just say more than anything, there's a lot of iterations.

So it was like a conversation between me and Joe and then it was like iterating on a first pass of like, hey, let's just see what we can come up with for two hours of brainstorming here. Let me show that to Joe quickly, just got checked like Joe would be like, oh, I don't actually care about this and this. What I really need to be able to say is this in the positioning message. And so I thought of it as like 20 iterations where each iteration was 30 to 60 minutes of thinking about it.

And then occasionally, an engineer team would be like, okay, well, we need to really run down what it's going to take to migrate these 50 services. And so that was a little bit more time intensive. But yeah, very active conversation between product engineering, Joe's sales engineering team who were like closest to the product and me. And that was kind of the loop we were in. I would say it was about a month of planning.

And we probably did about 20 iterations on this until all parties were comfortable. But I think the anti pattern here is like having an end go into a room for a week and figure something out without sort of checking with the sales engineers. We had some particularly awesome connections to Joe had a sales engineering leader in Amia that just knew the multi region stuff super cold in terms of what we needed to do where we cut scope.

So we got him Arthur's his name involved like super closely with the PM and the end leader who were scoping that. The three of them were like a working group for a long time doing like faster iterations bringing it to me and Joe. So it's like a lot of creativity on just how do we solve this problem regardless of who needs to be in the room. Like let's get everyone in the room and iterate together. Thank you for sharing such authentic at working the sales company that really resonates with me.

My question is a little bit follow up about your effort to build a platform. It's very easy to say and then I kind of feel the pain of that already taxing my engineering team. Can you share a little bit more about the strategy and more like how committed a leadership will be to make that happen? Yeah, these kinds of platform investments are always tricky. Yeah, I mean, we had several over the years when you're really leading like a true platform initiative.

It kind of needs to be a stop the world moment at time. Like one of the platform initiatives is an action the one Joe and I were just talking about, but we wanted to basically make it possible that anything you could do on the website, you could also do via API. We wanted like a full control plane API. And that was just a tough one where I had to kind of insert a top down mandate that one of these two quarters, you could either do it Q3 or you could do a Q4.

You needed to go like follow the spec against like the control plane spec and you needed to build out all of your functionality to match that API. For those kinds of initiatives, I like to lead with a really strong core team that goes and does it for the first couple product team so that they really understand almost as like the customers of needing to use the API patterns. They've set up how well it works. And so usually you can get the core teams to do about 40% of the work.

But then at some point, you got to like go and just top down from the rest of the product teams to go fill in some of that work. So those kinds of broad platformizations, I found to be particularly challenging and they needed to ladder up into those kind of year long missions. Otherwise, it just like felt like extra work. No one could take on. Maybe the other learning from the one that Joe and I were talking a little bit more about was having an internal customer.

And so first it was his sales engineering team and then it was his professional services team as the first customers was so powerful. Because what was happening was some of our biggest logos had always come to my team to go build a couple of random integrations into whatever services. They could now go to Joe's team. Joe could charge them $200,000 a year or whatever it was for this project.

And we would have a customer paying for the platform development against our own API and all of that was happening internally. Obviously we were very motivated, you know, if it's like Nike or whoever to support both the seven figure AR contract and then also sometimes the like six or seven figure services contract and all of that was happening with Joe's team acting as the customer into my team doing the platform stuff.

And so as much as you can set up that kind of situation, which comes from having an awesome good market leader who really kind of is not afraid to ask customers to pay for the things that are not part of the like vertical offering, but are things that they should be paying for. That was really the unlock for that sort of functions project that we were talking about. So anyway, TLDR, I think you need to have it be an annual strategy or something that ladders up to that kind of like time horizon.

You need to get everyone bought in and then as a leader, you can really like sort of sequence it out, get the core team to start the migration or whatever it is as much as possible and then get the rest of the product teams to fill it out. And yeah, have the good market team asking for what's needed for success. If there is some kind of build on the customer side, they can help with that as well.

If that demand is not really there, then you probably don't have an actual platform play and the good market team can help with that demand. That's all the time we have for questions today. Thank you so much to our panelists for a very engaging session. Thanks for having us. If you enjoyed the episode, make sure that you click subscribe if you're listening on Apple podcasts or follow if you're listening on Spotify.

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