Navigating from Start-up to Scale-up with LinkSquares' Tim Parilla

: Today's episode is sponsored by the RevOps experts at FullCast. With me is their head of customer success, Tyler Simons. Hey Tyler, revenue efficiency, sales productivity are everything today. How does FullCast's Go-To-Market Planning platform help RevOps teams achieve these types of goals? Well, FullCast lets you build better territories so that the right resources are always focused on the right opportunities. When reps are motivated and zeroed in on their targets, they'll be more successful and bring in more revenue. That sounds great. I do a lot of that planning in spreadsheets today and I'm pretty happy with my spreadsheets. How is Full Cast any better than that? You must get rid of the spreadsheets because spreadsheets create lag and errors. With Full Cast planning and updating happen automatically all in one place. Best of all, it automates all common headache-inducing planning activities like territory rebalancing, account hierarchies, routing, and more. So when you're faced with those go-to-market plan changes, which, you know what, they happen all the time, Full Cast has your back. All right, you got me convinced. Where do I learn more about Full Cast? Our website, fullcast.io. Hey everyone, welcome to Operations, the show where we look under the hood of companies in hypergrowth. My name is Sean Lane. One of my favorite inflection points in a company's evolution is when it becomes abundantly clear to everyone on the team that it's time to transition from scrappy startup to scale up. Scrappiness can turn into sloppiness. A single person is doing a mediocre job at five different jobs. And it turns out that you actually did need someone in finance to manage all your customer subscriptions. You get the picture. My guest today also loves this inflection point. And as you'll soon see from our conversation, he thrives in it. That guest is Tim Perilla, the chief legal officer at Link Squares, the contract lifecycle management platform that has raised over $160 million in funding, including a $100 million Series C in 2022, that value the company at $800 million. Prior to Link Squares, Tim spent seven years at DraftKings helping them navigate this same evolution. In our conversation, Tim teaches me about the functions that need to be created from scratch during this inflection point. We talk about how employee career growth can keep pace with company growth. And he breaks down for me why non-go-to-market functions should be held to the same data standards as their sales and marketing counterparts. To start though, I asked him to set the stage for us on what's typically happening in a company to signal that it's time to transition from startup to scale up. I would say that particularly early on in a startup begins where the founders are doing everything and then the founders recognize I can't do everything and I need to hire somebody with some expertise or someone to do the things I don't want to do or the things that I'm not good at or especially the things that I don't want to do and I'm not good at. It builds to a certain extent. Now you have some basic functions. You have whatever your go-to-market function is, whatever your build your product function is, whether it's durable goods or software. Then you have your back office, run a company, do payroll, just close the books, that kind of stuff. And then I think that can actually exist for a decent amount of time until you get to a point where you're... growth velocity is such that the things that are being absorbed by people who it's not their core competency to do that thing, they just don't have time. So for example, you know, here at Lynx, whereas when I first started our finance team, our like director of her title at the time was director of finance and our CFO, they were the ones who were collecting all of your documents and getting you to sign the I-9s. getting you set up in payroll and all of that sort of stuff. And they're, you know, they're using a provider, your typical startup provider, but they were the ones administering it. They were the ones who were choosing benefit plans and things like that. And basically, finance was doing all the stuff that the founders didn't want to try to get people on board. The CTO and the CEO were the ones who were actually provisioning laptops and getting them set up and handing them out to people. Right. you get to a certain point where it's like, okay, now there's enough work where like, it is going to take me a disproportionate amount of time to actually fulfill this function. We need to hire somebody for it. And again, I think you go from that small team, everyone does everything. Now, usually you have either an acceleration point in your sales where you have more top line revenue coming in, or you have a new round of investment. that comes in that allows you to move faster. And then that will be the impetus for, okay, now we need some supporting functions. We need to start scaling things up. And so it's hard to say if there's like a moment in time, I think the hallmarks of being overworked on things that are not your core competency for your current staff should tell you that you need to start hiring experts in those areas. When you look across multiple companies, Tim says that there are a number of triggers that might serve as the catalyst of knowing when it's time to start scaling your team. But to make this even more concrete, his point is simply, look, if you have people doing a lot of work in areas that aren't their core competency simply because there's no one hired yet to do that work, it's probably time to start thinking about further specialization or adding those new functions to your business. So what functions should those be? We all know the names that companies assign to different departments that sounds like things we should have. IT, HR, finance, ops. But we also need to figure out how to map those functions to the needs of the organization at that moment in time. It's not one size fits all. And Tim says it's not just a moment for the company to consider what's best. It also creates an enormous opportunity for the right team members as well. This is where you have a lot of really great opportunities. This is why from a career path and perspective, if one is flexible enough or ambitious enough, or maybe stubborn enough, going into a startup is a great idea and is a great career opportunity because usually you, you need player coaches, you know, I came into length squares and I was immediately reviewing NDAs, right? And. At the time I was 13 years into my career and I hadn't reviewed an NDA in many years, right? But like come in, you gotta be a player before you can be a coach because there's only one of you, right? And just like the person who you're gonna hire for HR for example, you want someone who knows how to administer payroll and maybe has done that at some point in that person's career. You want somebody maybe who's done some recruiting before. As well, like it depends, are you going to be hiring a lot of people? Okay. Maybe you want somebody who's better on the recruiting side and less on the HR operations side, maybe you're not going to be growing that fast, but you just know that there's enough administrative work around there and there's learning and development that needs to happen and so on and so forth. You just kind of think about like what those areas of expertise are, but. for people early in their career. Okay. Yeah. I'm good at being this player. And now as the company grows, maybe you get one or two direct reports and your focus starts to change on how do you organize those resources and moves a little bit away from I'm going to keep doing NDAs, you know what I mean? And I think I want to look at that from both sides, right? Like the side that you came at it from, but also for those folks that you mentioned that kind of came in as players and then have the opportunity to grow into coaches, something that somebody talked to me about a lot earlier in my career was it's really hard to keep pace with the growth of the company as an individual, right? It's really hard for your career to grow at the same pace as the company. And so how have you seen. folks who came into those kind of player roles at that inflection point of the company, successfully keep that pace? Because it's not an easy thing to do. You're right, it's not an easy thing to do. There are a few aspects of it. I think number one is having an awareness of your own limitations, and then being honest about that, right? If I'm coming in and maybe I'm the first HR hire, and I've done... maybe just the HR operations side, but it's going to be a lot of technical recruiting, one of two things is going to happen. Either A, there's going to be somebody brought in above you who has that good recruiting background, or B, you are going to have to say, I need somebody to do this because I'm not good enough at that. I can manage this person, but I can't do what this person does. right? And be able to be confident enough in your own abilities to do something like that. The other side is that you may not, it really does depend on where you are in your career, right? Because you may find yourself in a situation where you are the right person to lead a team for a period of time. Right? I think about hires that I make here at link squares, and I'm looking for the ideal profile of candidate for. the next 18 months to two years, not the next five years. You have to shorten that timeline a little bit and say, is this person the right person? And then I think when you're hiring too, you have to be pretty honest with the candidate and say, this is my vision for you in this role, right? You're the successful candidate, but it's really up to you. It's really up to you and whether you're able to scale with the company. Some people are and some people are not. But I think you setting that expectation upfront is critical, right, and probably something that not a lot of people actually do, even if they're thinking it in the back of their minds, they don't actually communicate that to the candidate in a way that's constructive. And then I think also, probably the way that you would manage that person, and the way that person takes the coaching and feedback that you're giving them, change in a pretty constructive way when that's kind of out there and on the table. It's like, all right, we've got this timeframe to figure this out together. And at the end of this timeframe, like you'll have developed in such a way that you're prepared to take the next phase of growth step with us, or just like we talked about at the beginning, now it's time to change our approach. Right. Exactly. And the needs of the organization change over time as well, particularly when you're looking at sort of more of the support functions in particular. And I hesitate to call that operations because in many, many ways that's not at all, particularly with the support functions. The CFO that you have for, and oftentimes even the CEO that you have for those early stages where you're really like creating your market and showing your product market fit is going to be a different profile than maybe the person who is going to just be milking the cash cash. you think about it like anybody you've worked with at any startup, they're really good at growing things. But if you tell them like, okay, cool, we've grown enough. And now I want you to just operationally get as efficient as possible so we can squeeze as much money out of what we currently have today as possible. I think what you find is two very different profile of people who are good at those two different things. It's rare that you guys someone who's good at both and happy in both scenarios. It's easy to think about the dynamic of who can scale with the company as something that only happens at the frontline leadership or functional leadership levels. But Tim's right, this dynamic holds true all the way up to the C-suite. And it's not just that some people can't scale up, it's oftentimes that they might not want to, or they don't find enjoyment in that next phase of the company's growth. I also think it's worth pausing and giving Tim some credit for the way he came into Link Squares and the approach he took to the actual work that needed to be done when he got there. He was more senior in his career and all of a sudden he found himself as the sole person responsible for NDAs. And guess what? He adjusted his expectations and handled the NDAs. I haven't found it to be super common for folks coming from much bigger companies to that might be missing a lot of the expected infrastructure they've grown used to. Tim said though, it's not so much about the company you're coming from, but more about what you learn about the role you're going into. I would say that you try to figure out in the current role how much of the minutiae makes up that role. Whether the candidate is managing it, but also intimately aware of what it takes to do that job still. Versus, I haven't talked with the people who are doing contract review in a quarter. I get a readout, a report, this is what's happening with contracts and then I move on with my life. I'm not actually working with these people day in and day out. I'm not reviewing their work, right? That sort of thing. You try to figure out like, okay, are you like so far removed from the weeds that you have a lot of rust to kick off if you were to actually get pushed back into the weeds? Versus, yeah, I may not be doing that work, but I'm close to that work still. At least for me in a weird way, I do kind of enjoy revealing contracts. Like it can get really boring sometimes, but in a way I do like the negotiation aspect, I do like the drafting aspect. I do like trying to come to a solution. People are pushing back on certain things for a reason. And if you can understand that reason better, oftentimes you can figure out the right way to. make both parties happy and set things off on the right foot. It doesn't have to be a win-lose, it could be a win-win or a compromise, I guess, is maybe a different way to put it. But when you're talking with candidates, figure out like, did the candidate look at that part of the candidate's career as a necessary evil, or was there still like some level of passion around it? As weird as that may sound. So those are kind of the things that I would look at. And then I think it's worth being. completely direct and saying, you're going to have to roll up your sleeves and do this. Are you ready, willing, able, and capable to do this? Probably for a little bit longer than you think you're going to have to do this. I mean, I was reviewing contracts for over a year, right? Before really my VP of legal told me to please stop and he's got it. He doesn't let me anymore. This episode is sponsored by Fullcast, the company that helps operators build better sales territories. Their platform focuses the right sellers on the right opportunities, making them unstoppable. And the cherry on top? Fullcast automates common go-to-market activities like territory rebalancing, account hierarchies, routing, and more, so the plan is always in sync with operations. With Fullcast, say goodbye to go to market planning headaches and hello to your own personal planning assistant. Learn more about Fullcast today by visiting fullcast.io. Okay, back to Tim. We've talked a lot so far about the people side of the transition from startup to scale up. I also wanted to explore with Tim the functional evolution that also takes place, particularly with the non-customer facing functions. The reason I want to focus on non-customer-facing teams is that the customer-facing functions were probably already there in the first place. You need a sales team, you need a post-sale or customer success team, and we largely know how to measure those teams. It's easier. It's a little harder, a little squishier when you start looking at operations or finance or legal. It's not just about standing up those functions at this moment in a company's evolution. It's about standing them up in a way that has the same accountability as the customer facing teams. How exactly do you do that? Here's Tim. There's got to be some level of SLA that's established, right? And I immediately come at it from the perspective of the legal team, where it's like, we use data. We know what our turnaround times are on an average basis. We know what our turnaround times on a per document basis are, right? We can look that up. We track that. We monitor that. And we can say we worked on this many deals during this timeframe that ended up closing and resulting in this amount of revenue. So being able to show that is really compelling. When you start to think about maybe some other functions, an HR function, everybody's gonna have some metric that they can hold onto. HR is your employee health scores, how employee satisfaction surveys. things like that, are you hitting your hiring goals and what's your attrition in the first six months, 12 months, 18 months, so on and so forth. There are different metrics that you can use. I'm a big believer that if you don't have data, if you lead a function and you don't have data showing that positive impact that your team is making to the rest of the organization, then you're simply not good at your job. You can do everything else well, but if you're not bringing data to show your contributions. and providing context around that, you can't possibly be good at your job. And that may be hard for some CFOs to hear, that may be hard for some chief legal officers to hear, but it's the truth, right? Everybody else in the organization has to come to the table. Imagine somebody, imagine your chief marketing officer coming to a quarterly business review and just providing some anecdotal, hey, we made this commercial and it aired a bunch and like... People thought it was really funny. Oh, great job, CMO. No, like it's never going to fly. So why is it that some of these support functions can get away with walking in and saying like, Oh, I talked to like a couple of people who are major consumers of what we provide to the organization and they're happy. Okay. Great. Well, as long as they're happy, that's good. So that's like sort of one part. The other is, well, how do I know if you're any good at what you're doing? Like just because the people you work with are happy with working with you doesn't mean you're doing your job. Well, right. Doesn't mean that your core competencies are strong. Doesn't mean that you're holding your work to a particular standard of care. Right. And so I think bringing data into the mix gets rid of those anecdotal feedback. And again, like I think every executive needs to demand data from. anybody who reports into that executive. If you are managing a function, you have to bring data to show how you contribute. If you're not doing that, it's a huge mess. It's a huge mess and nothing else that you're doing really matters. I gotta be honest, I love this. And I'm sure every marketer, salesperson and customer facing employee listening to this is nodding along violently to their headphones right now. If I'm in marketing, and every single campaign, every single dollar I spend is going to be scrutinized and measured, the same should apply for these new functions being built in other parts of the organization. I think the best way to apply Tim's lesson here is, if you can, set these expectations as the functions are being created. That way, they are ingrained in the DNA of the teams from the very beginning. And what you end up with is a mentality like Tim's. When people ask him about the utility of his team, he doesn't get defensive. Instead, he views it as a core part of his job description to proactively communicate what his team is doing. Earlier in my career, I was at a company and I was going through this exact same transition from startup to scale up and one of the best things I did was start to send a monthly recap to my boss and to the CEO about my team's work, the metrics attributed to that work and the achievements and shortcomings of the team. That email removed all doubt of the utility my team served and I leaned into the lesson that Tim is now sharing with all of us. But doing it from the beginning, I get it, is not always possible. So how did Tim instill this mentality when he arrived at LinkSquares? Well, the other stakeholders in the organization, it's easy, especially as a lawyer. You bring like one stat in the room and people are like, oh my god. The bar is low. This is awesome, right? Getting that stakeholder buy-in from people who are otherwise required to bring data, they like, you're doing this too. Awesome. That's really easy. I think getting your team to buy in, you have to two things. Number one, actually getting people to buy in and care about it above and beyond just mandating like you have to do this in this way. is really helping people to understand the end state that you're trying to get to and why it's meaningful because oftentimes to gather the data in a way that maintains integrity of that data and provides the basis for decisions and truly shows a meaningful impact to the business, you as an organization are going to go through some inefficiency for a period of time, right? You're going to introduce process. And I think the art to it is how much process versus what you get out of it. But you have to tell people, listen, to endure this process, you will actually end up taking longer to get particular things done today. But at the end of the quarter, when we have to report out on what we've done, it's going to be very easy and immediate. Right. It's kind of like keeping your room clean. If you do it once a quarter. It's going to take you a long time, but if you clean up a little bit every single day, it really isn't that big of a deal. But realistically, you've got to sell that end state of, Hey, wouldn't you love it if you could go into a meeting or put on your LinkedIn profile that while you were managing the contracting function at whatever your job is, that you maintained turnaround times of 0.65 days and saw the growth of the contracting function from. 1000 contracts a month to 100,000 contracts a month. Those things are really impressive. And to be able to bring that data to the table is a really important thing. And so if you can get people to the point where they buy in like, I want that in state, I want to be able to say those things. It's like, well, how bad do you want it? Do you want it bad enough to have to take an extra five minutes for every contract to run through the system? or change your process, right? Do you want this as a department enough to change the way that you work so that you can collect these things and you can identify inefficiencies, right? Things like that. So, and it works the same with any other department outside of legal. You've got software that helps people identify how efficient or inefficient the function may be. I think there's also kind of like a maturity curve there too where Maybe level one is what you're describing where, okay, we want to figure out where our team wants to get to, right? And you have metrics around what that 0.65 days of turnaround. And then I think the next step, and you tell me if I'm thinking about this the right way, like I think the next step is like, okay, what does that 0.65 days do for business outcomes? Then how do we connect that? And I think that's where people like people really start to open their eyes. We're very proud of it. I think the legal team that we have at Drift is phenomenal. And I think that. they have become a competitive advantage for us in actually getting deals done. Like I think we could point and draw a straight line between win rate and that team in terms of days from contracting, starting to contracting closing, right? And all of a sudden you're tying that back to a real business outcome. And so is that the next step when you say this is where you want to get to, then it becomes, all right, not only are we contributing these internal efficiencies, but it actually drives. bookings, retention, whatever it may be. Yeah, absolutely. I think, I mean, you connected it immediately. That's exactly right. I mean, I think anecdotally, anybody in sales will tell you that a longer sales cycle is probably not good, right? A shorter sales cycle is something that you want. And so even if it's just even to a certain extent, no activity is bad activity, right? Where it's, all right, well, that contract with someone who's like really excited to buy our platform. and get on with it, start using it. Now, you know what, been sitting on it for two weeks and maybe that buyer's in a different mood. Maybe something else happened within the organization, especially economic uncertainty can play into things and what budget you think you have today. You might not have tomorrow. Passage of time can be problematic and usually is problematic when it's unnecessary passage of time, right? And so if you can shorten those sales cycles. you know, it's going to have a positive impact on the revenue. But what I like to think about there is it's not enough to just have the data. You have to contextualize it and that's contextualizing the data. So that's not just showing, oh, for our own sake, we met this SLA. It's why is this SLA important to the business? Right. Drawing that that's where it takes collaboration with other systems that you have and other leaders that you have to say, I want to figure out what's going on here, here and here and how we impact. First and foremost, if you're even at all questioning whether or not your legal team can be a competitive differentiator for your company, stop. I've seen it first hand with the Drift legal team, and I'm not sure I could ever work somewhere again that didn't have the same level of responsiveness, accountability, and partnership that I saw there. Second, I think the important takeaway here is Tim's point that you can't just bring the data. You have to also contextualize that data with business outcomes. Only then will your team's impact sink in with your audience. This is incredibly applicable for operations teams too. We, along with other quote unquote support functions, need to be able to articulate the scope of the work that we do and the data that supports our impact. And according to Tim, you're going to need that information to be crystallized when you're making the argument for these teams to both exist. and to grow. When you start to dig into that, when leaders at different levels of the organization start to think about that, and maybe get out of the day to day for a minute, and think about, okay, what is my team really doing here? And what problems are we seeing that are constantly coming through? It actually can lead to great innovation as far as elements of that customer lifecycle that... the company maybe never even realized existed, or never thought that it was gonna be a pain point. Now they're like, oh, this is actually a blocker for X, Y, and Z, let's spin up this function that handles just that blocker, right? Maybe that's one person, maybe that's a hundred people, right, depending on your organization. Untangling that spaghetti mess that happens with every company going from startup to growth stage and beyond. Untangling that spaghetti mess of the customer lifecycle, I think provides an opportunity for innovation, an opportunity for clarity of problem that needs to be solved. ["Spring Day"] Before we go, at the end of each show, we're gonna ask each guest the same lightning round of questions. Ready? Here we go. Best book you've read in the last six months. Best book I've read in the last six months, probably Play Bigger. I forget who it's by, but Play Bigger is a good one. All right, put it on the list. It's awesome. I'm gonna consider you an honorary ops person. I would typically ask about your favorite part about working in ops, and so I'm lumping you in with ops here. That's fair. I oversee ops at Length Squares. So my favorite part about it is exactly what we were just talking about. Really, this is what we did at Length Squares. There were a group of about 15 people who did. now probably four to five, maybe six different disciplines. But there is a group of people who are really good at all of that. And so now what we're trying to do to scale is build these machines, right? And these specialists. And it's been awesome seeing people who particularly at first may have been a little hesitant and a little territorial like, I do that. Why are you taking that from me? It's like, so that you can do other things and get better at what you're really good at. And then having people come back and say like, that was awesome. This is so much better. This is working better than it ever was. There's no way we could have handled this many customers doing it the way we were doing it before. That's what I love most about it is that it's a true problem solving thing. And it's unique, right? It's not like you can go from one company. It's not like establishing operations at draft Kings is the same as doing it at wayfarers, the same as doing it at like squares or. Salesforce or Xerox, right? It's different, but that's probably my favorite thing is just when you start to see results and people who are skeptical are like, ah, wow, okay, I get it now. And I get that we can go from 200 customers to 2000 customers using this. It's a great feeling. Flip side, least favorite part about working in ops? It's a good question. I actually really enjoy it because I'm also coming from a legal background where sometimes the work can be a little bit And I feel like there's never really a dull day in operations. I'd say the least favorite thing is when you do have some problems that you know, need fixing and you just can't get the resources to fix it, whether that's on the human side or whether it's, I can't get them resources to have this tech fix. Right. And you just, then you have to pour more human capital into it, which destroys your cogs. and your gross margins and things like that. And it's just kind of like, that's really tough stuff. I also don't really like being told to wait or to slow down or we'll get to it. I want everything to happen as soon as possible. As soon as there's an idea, I want it to be there and be done. Speed, velocity, and patience is not a virtue that I really have. So I'd say those things are good. I'd say you probably have that in common with a lot of our audience as well. Yeah. All right, someone who impacted you getting to the job you have today. Tim Dent, Tim Dent was the CFO at DraftKings, became the Chief Compliance Officer at DraftKings. I also worked with him before DraftKings. He's been just an incredible mentor. He's not a lawyer by trade, and I think that's probably the best thing that's ever happened to me, having a real mentor that helped me to understand the business side of practicing law and helping to articulate. the problem that he sought to solve with adding a legal function. He's easily the one that comes to mind, an incredible professional and even better human being. That's awesome. All right, last one. One piece of advice for people who wanna have your job someday. Figure out what your core competency is and be really good at it. What I mean by that is I do consider myself to be a very good lawyer. I take a lot of pride in the legal work that I produce and I take a lot of pride. in the work that my team produces. Like it sounds cliche, but typos, even if they're in emails are not good. I get it how ridiculously pedantic that can be, but at the same time, it's not about your capability of whether you can recognize and identify typos. I think it's a reflection of how much you care about what you're doing and how much you care about the output. And so find that something that you do really well and do it really well first. After you've done that, you need to understand how well that particular discipline you've chosen fits into the organization at large. And then try to learn as much as possible from other people who are good at stuff that you're really bad at. If you do that, I think you end up in a pretty good place, right? You have your expertise and then with the expertise, you just try to gain as much perspective as possible as to why your expertise is even necessary. And if you can do that, you can probably make a pretty good career for yourself. Thanks so much to Tim for joining us on this week's episode of operations. If you want to hear more from Tim, Tim has his own podcast called cockpit council, which you should absolutely check out. Also want to give a special shout out to the legal team at drift, Zarina, Sarah, Jake, they were the best that I've ever worked with in my entire career. And I couldn't make it through this episode without thinking about them over and over and over again. If you liked what you heard, make sure you're subscribed to our show to get a new episode in your feed every other Friday. Also, if you learned something from Tim or from any of our guests, make sure you leave us a six-star review on Apple Podcasts or wherever you get your podcasts. All right, that's gonna do it for me. Thanks so much for listening. We'll see you next time. Today's episode is sponsored by Fullcast, your go-to-market planning platform. If you've ever spent hours or days building territory and quota plans only to have them be out of date the second the reps hit the street, you need to check out Fullcast. With Fullcast, you set intelligent, rule-based policies that automate all of the time-consuming, manual tasks that hit rev-ops teams throughout the year. With virtually no effort, operations will always seamlessly align with your plan. Learn more about Full Cast today by visiting fullcast.io.