Jared Fliesler (ex VP at Square, ex COO at Scribd)

Hey everyone, this is Erik Torenberg and you're listening to Execs by On Deck. Execs is a show for founders, operators, and leaders who want to understand the playbooks, frameworks, and tactics that leading tech companies today have used to scale. Our guests are tech execs in key roles at top tech companies who share their hard-won, earned secrets on how to scale faster. Today's guest is Jared Fleisler. Most recently, Jared was COO at Script. Prior to Script, Jared was a VP at Square, director at Google, and a GM at Slide, where he worked closely with Keith Rabois and Max Levchin, respectively. In this episode, we discuss symmetry and execs' ability to hire and fire, How to build world-class onboarding experiences, what it means to be vulnerable as an exec, hiring an exec team, and much more. Jared's an active angel investor and advisor for early-stage companies. He encourages promising founders to reach out to him on AngelList. This is the 3rd time I've interviewed Jared for a podcast. I thought he'd make a great first guest and didn't disappoint. Here's Jared. Jared, this is the first episode of my official new podcast, but it's the third time I've interviewed you. And we do it every few years or so. So welcome back and thanks for joining.

Yeah, thanks so much for having me. Excited to talk.

Well, first let me just say that every time I interview with you, we need a few years before you forget how the last experience was before you agree to come back on.

Yeah, well, you know, I'm still working through it, you know, some of the lessons that I've learned, but it's okay. Yeah, exactly.

The first one was more of a— for people who want to listen, it was more of a mission or how did you get to where you are spiritually and energetically. The second one was more tactical around the COO position. And this one will be also more tactical but around career progression and growth as an executive, building out an executive team. So maybe let's start there. You were at Slide. Slide sold to Google. You spent some time there. Then you were at Square and then most recently COO at Scribd. Why don't you talk about the different roles that you had at those organizations and how you've sort of grown as an executive and why you took the— or evolved with the roles that you did?

Yeah, well, I was very, very new in my career when I joined Slide. That was my second job a year out of college. And I started out in a company that was about 50 people when I joined. And so the culture of that place, this was early 2000s, It was just about let's work really hard and run towards this idea of building something successful in social media. We didn't really know exactly what it was going to look like, and it morphed and changed quite a bit, and my role morphed and changed with that. So I started out in business development and then started to work on sort of what we later would call growth hacking, but that term didn't exist at the time. Ended up running a product team and getting more technically inclined, joined the executive team. And so that was sort of the most change, I would say, in my career of being in one role or a set of roles at one company. When we sold the company to Google, it was really different. We killed all of the products that we had built and we started to think about new products at this intersection of social, mobile, and local and how Google could become more of a social company. And that was for about a year of running our team at Slide within Google. thinking about those new products. And so Slide, I joined, there was existing products, some new products coming out, and I was starting on the business side. When I went into Google, it was really starting on the product side and thinking, what new products should we build and how do we sort of get to where we want to go? What can we do that's different in this space? And then when I joined Square, it was very different, right? It was focused on very established products and thinking about how do we grow and scale our efforts around these products and around a few new products. But it was a mix of hardware and software. We were in the early days of marketing and thinking about the channels that would help us grow. Totally different customer base, totally different product, working in payments and working across teams like risk, retail, paid marketing, a variety of teams that I hadn't really been focused on running in the past, in addition to growth product and some of the things that I had worked on previously. And so each role was really different in terms of stage of the company as well as sort of what I was doing functionally. And then all of those really came together when I became COO because I sat across most of those teams that I had managed throughout my career. And so it was kind of the culmination of all those things coming together.

Yeah. And when you look at the experience that you have now, you've worked at a number of different companies for a number of different leaders, right? Max Levchin at Slide, Keith Rabois and Jack Dorsey at Square. Of course, Google. And so you've seen different styles of scaling and of company building, and then you were able to sort of implement your own at Scribd. How have your beliefs on company building and scaling evolved as you've seen different styles?

Yeah, I think sometimes you have choice in it and sometimes you have less choice in it. And I would say out of all of my experiences, Square was the place where it kind of felt like we had the least amount of choice. And what I mean by that is there was so much demand for the product and the need was so great. We were scaling so quickly as a company that we were really struggling with this hypergrowth of going through this experience and going, well, we want to really maintain our values and the types of people that we're hiring and be really diligent about that. And at the same time, you know, we're trying to hire 100 people in the next 90 days, you know, and that was the one place where I really experienced that. Whereas we got to be, we just had more time. And so it allowed us to do certain things that you really can't do if you're in hypergrowth or they're much harder to do. And so for me, that was a really different experience. I built a lot of empathy for that. I think before I would've said, oh, you just should hire slower. And yeah, that sounds like an easy solution. But the challenge is if you have things that are breaking, if you're a business that works, for example, on compliance, You don't get to decide when Visa says, hey, if you don't have this department in 90 days, then we're going to shut off your payment access. So some of these things are not your choice. They kind of happen to you. And so you do the best that you can in those environments. I do think that in general, one mistake that companies make around this is that they hire as fast as possible. And in reality, hiring people that are not a fit for your company While it may feel like the right thing in the moment as you compromise around your values or you say like, I'm going to accept this B+ player even though they're not A+, it may feel like, oh, I'm plugging that gap and this is better than not having someone. I think you have to be really cautious when you do that. If you introduce people into the company that you ultimately need to remove from the company, your timeline for actually filling that role with a good person is actually longer. You've just artificially gotten yourself to believe that you fixed the problem, and in fact, you probably made it worse. And so, there's a discipline that you have to learn as a hiring manager and as an executive to slow down, remove things from the roadmap, hire slower, even if it's available to you, if you feel like you're compromising too much. Now, that said, I don't know that any company has hired just A+ people. I don't know that that's possible. I'm not Miss Cleo. I don't have a crystal ball that allows me to predict if somebody's in BA+. But I think we all know when we interview somebody, we go, maybe they're good enough. And when you walk out of a conversation like that, I think you have to have the discipline to fight another day and find another candidate. And I do see that as time goes by, it taxes a team and a lot of people start to cave to that and they start to really bend what their must-haves were. And so I think it's really important to be clear about what are the must-haves, what are the nice-to-haves, and make sure that you don't compromise on the must-haves. Those are still must-haves even if you're frustrated that it's taking so long. Yeah.

Keith Rabois has this point around, I think everything you said is true at the same time, don't optimize for zero defect hiring. And I think when you have 70% conviction, just go for it. Have you tweaked your hiring algorithm over the years at all in terms of either making mistakes of people you hired and then said, actually, this is a trait that I didn't see upfront, but now I'm not going to hire for it, or vice versa of like, hey, I was too harsh in this way and maybe I should have been more lenient and now I'm more sympathetic to it?

Yeah. I think my relationship and kind of the coefficients that I put in my hiring formula, if you will, around what's important has really changed over time. I've also hired different kinds of people over time. I've been in different roles and the people that I've been recruiting have been really different. And so I'm not as focused on hiring the same roles that I was hiring 10 years ago. And so it's a little hard to freeze time because I haven't been doing the same thing for 20 years and to look over that. I think Keith's right. You will go into analysis paralysis if you try to get to zero defects. And the thing that I think about for companies that are rapidly scaling is You better get as good at firing as you are at hiring. You have to have symmetry in those capabilities. And I think a lot of companies develop an ability to pull people in and to recruit really aggressively without developing the same ability to push people out very quickly, to manage them, to understand whether or not they're going to be a good fit. And out of respect for them, And to do what's best for the company, you need to communicate that really clearly upfront early on. That's the part that I see missing. And this is the same thing as kind of working on okay product features or okay business lines, right? Like, that is a death trap. And so sure, you can test something out. Failure is totally fine. Hiring people that don't work is totally fine. You just better fail fast and you need to be really honest with yourself and with them. And so that's something that I definitely think about and encourage in my teams.

Let's unpack that. What are your tips to firing well? Because maybe it's as simple as if there is doubt, there is no doubt. At the same time, sometimes people get doubt too quickly and they're like, hey, I want to give this person a chance. I didn't set this person up for success. I feel guilty about that. Maybe in a different role or maybe we could have a reset moment around it. What are your tips and your philosophies on firing well?

Yeah, I don't agree with, if there's doubt, there's no doubt. I mean, I think if we're all honest with ourselves, we probably doubted ourselves in roles. Like, the term imposter syndrome comes from somewhere, right? So, yeah, I don't really think that that's a good line to follow. I think that if there's doubt, talk about it, communicate. And the number one thing that I think leads to challenges around this is people start to have concerns, And they don't talk about it. They don't have the communication. They don't have the open correspondence with their employee. They're not talking to their manager about it. They're not sort of like working towards figuring this out. If there is a problem, I think it's worth surfacing and trying to figure out a solution and staying in a mindset that is solutions-oriented. What is the outcome that you're trying to get to? How do you communicate that outcome? How do you set the right goals and expectations with the employee and then help them to get there? And if they can't get there, then you have a different conversation. But if you haven't communicated what the challenge is or where you're hoping that they get and try to help them to get there, then you are not really acting in service to the employee. And so I think that's where you start. You start in that conversation, you make sure you're being clear. And the same thing is true when you're interviewing people. I remember I joined a team and I was talking to the engineering group and it was clear that they felt that their job was to figure out why someone probably wasn't good enough to join our team. Like that was, they were the protectors of our team. They were supposed to keep them out, you know, make sure the weak can't get out. And then in some crazy circumstances, maybe people can break through the wall.

Yeah.

And I actually think that's wrong. Like in the interviewing process, in the early stages of an employee's development, Your job is to help them succeed. And when you're interviewing somebody, you want to help them succeed. You have way more information and expertise about that thing than they do. You've been doing it for a while. You've been thinking about it. You've been in 20 different meetings where you've talked about it, right? And so, the expectation that they're gonna come in and be as much of an expert as you are is just an unrealistic expectation. Now, if you help them succeed, and then the next time you help them a little bit less, and a little bit less, and a little bit less, great. That's them learning that, and that's you being a manager and teaching them how to do this. You're testing their capacity, ability to pick things up, ability to learn, and what you believe their ability will be in the future. It's not testing if they have every perfect answer on day 1.

Yeah. And in terms of setting them up for success, what's your philosophy on onboarding in terms of what you've learned that's maybe not obvious on how to do that well or how to set that up well from a company perspective?

Yeah. So I think there's 2 parts of onboarding. I would think about this generally as like there's general onboarding, which basically everybody goes through or should go through. And then there's job-specific onboarding. And when I was at Square, we developed an onboarding program that was very extensive. It was a week long. We had every leader from the company come in and speak about their areas of what they do. And the goal there was, especially as you were doing hypergrowth, you get all these people coming in, you want them to understand how the company works. You want them to understand how the pieces are connected. and why you're doing that work. And if you don't do that, people get into this mode of just sort of like taking tasks and completing those tasks without understanding how does the work that I'm doing sort of relate to the work that my team's doing, and how does that relate to the work that all the different teams are doing, and how does that relate to what we're trying to achieve as a company? And so a lot of the purpose of onboarding is connecting those dots and also giving them a little bit of a map of the organization to say, Hey, if I have questions about this or if I have concerns, I know that Jared does this thing or that Bob does that thing or that Jen runs that area, right? It gives them an understanding. It's like an overview of how the organization works and the work that you're doing, how you're doing that work, what guides that. But it's a lot of the how and a lot of the history. Because I think one of the challenges that companies face is when you're growing from 5 people to 10, it's pretty easy to keep the culture really tight and consistent. When you hire 30 people next week and you're bringing them on altogether, it's very difficult when the person that hired them has only been at your company for 90 days and they don't even know the full history, right? And so you're really trying to create a baseline where you have, at Scribd, we would call this the Scribd historians. You have the historians of the company, of the culture, that are really imparting that knowledge on the new people that are coming in and trying to maintain that culture as much as possible. You then have job-specific onboarding. General onboarding, you're not going to be able to cover everything that a person needs to know. And so I generally believe you should have an onboarding plan that covers everyone. That's sort of a general program. It might be a day, it might be half a day, it might be a few hours, it might be 2 weeks. It kind of depends on the size of your org and how much you want to cover. And then you have job-specific onboarding that's generally done by the hiring manager, and that covers what this person needs to do in their role. It's generally more team-specific, helps them understand where are assets, where do I go for these things, how do approvals work, what meetings do we have, you know, all the basics of how they can succeed in their role. As you get really big, you might introduce sort of more steps or modules in between. You might have a module for things like managers or executives where all managers go through a module around what it means to be a manager in that organization. You kind of, you want to have only relevant information in an onboarding so you're not wasting people's time and it stays interesting. But you also want to make sure to cover populations as they grow so that everyone kind of knows what's going on and how the company works without it being really inefficient so that every hiring manager is having to teach every little thing to every new employee.

And when you think about, you know, your early teams kind of have, Square and Slide, et cetera, have their own organic culture and then you have to be more deliberate about it as you grow and scale. But there's also opportunities to— one is translating the culture, the historian example. Another way is growing and evolving the culture in terms of what worked for 20 or 30 people just won't work for 400 people, especially when the 20, 30 people all knew each other well, et cetera. How do you think about evolving versus growing culture or just having great culture as you scale?

Yeah. I think it's probably the hardest thing that you have to do, to be honest. And I think that many companies try to hold on to things that stop working for too long. It's sort of like something breaks, you realize that it's no longer serving you or serving its purpose in the organization, and now it's a problem. So, to be clear, it's already broken. It's already not working. Now it's a problem and you just start working on how to solve it. And you probably bump into the walls a few times. It's not like you just try something new and it magically fixes it and it's perfect. And so you end up fixing that cultural problem 6 months, 12 months after it started. And so now you have whatever that amount of time was and all of those people that were impacted by that in your organization. And you've got to think about, well, how do I change that? How do I refresh that? How do I go back? And so I think it's good for teams to revisit this, to revisit their values, revisit what they believe their mission to be, revisit their roadmaps. And most companies do this on about an annual basis. They do annual planning. They start to think about what they're prioritizing and how that connects. And they kind of go back out to the team and remind the team why they're doing what they're doing and what they're trying to achieve and how they're trying to get there. I think it's great to have a 10-year vision and an idea of where you want to go long-term. That tends to be kind of fuzzy. That thing tends to be some big audacious goal that's not super specific in the work you're doing right now. It's kind of hard to see how it's connected to that. I think the 1-year plan that's zoomed in much more, that needs to be much clearer. And that's the thing that probably changes year to year the most. It's really, how do I take what I think we want to achieve longer term and translate that into the nearer-term milestones or nearer-term outcomes that we're going to deliver in a way that's inspiring and aspirational, but also realistic, so that the team's actually motivated by it? And how do you look back? It's a really important thing to own the accomplishments, but also the failures. Like, where were you wrong? Did you take the time to reflect on that and learn from it? Pretty important thing to do, right? And so if you're honest and open about that and you communicate back to the team, hey, we thought that building a rocket ship was going to be the right way to get to the moon, but it turns out it's better to build this other thing instead. That's okay. You should talk about why you felt that way, what you've learned from it, and how that changed your plans going forward. And then So here's our plan going forward. Taking those lessons into account, this is what we're going to do. We're still trying to get to the moon. We're still trying to accomplish this goal. And so people maintain that motivation and excitement and they understand that it's okay to be wrong, to make mistakes. Having that culture of vulnerability and of failure is so critical to innovation. And so you're teaching that at the highest level and instilling that in the culture. I think the biggest mistake that people make is having culture happen to them. Instead of having it be something that you're proactive and you talk about. And in the absence of a narrative, people will create their own. And they do this around social issues. They do this around your values. They even do this when you say, hey, this is what we stand for. They interpret that in a specific way. And so, I think you have to talk about what you mean, not just the words, but like, what do those mean to you? Why are you setting them up that way? And you have to repeat it regularly in order to make sure there's consistency across the company.

I want to get to annual planning in a bit, but let's actually pull that thread of vulnerability for a second because it's 2021 today. We don't know how Andy Grove or Steve Jobs would have handled some of the topics that employees bring up today, but times have changed. And you've worked for different leaders that have different styles, of course, and they work for them in various different ways. But I'm curious how you've thought about the tension between having very high expectations and the stern disciplinarian culture that maybe Andy Grove promulgated or the more vulnerable. There's a spectrum. These are not mutually exclusive in any sort of way, but I'm just curious how you think about that.

I think people sometimes misunderstand what vulnerability is and they put it on an axis that is at the extreme opposite end of things like courage and discipline and bravery and conviction. And they talk about vulnerability as if it's weakness, and it's something where it's when people have no idea what to do and they're overwhelmed and they're vulnerable and they're exposed and they're just waiting to be attacked. I think that's a really bad form of vulnerability. I think vulnerability is about being open and honest your team around the challenges that you face and around what it's going to take to succeed. That requires a lot of confidence in you as a leader in developing a plan. And I think being vulnerable is about sharing the responsibility in success foundationally, right? And so when you're not vulnerable, when you approach it with too much conviction, like you have every answer and you have it all figured out and you know with absolute certainty that if you do X, Y is going to happen, there's a couple of things that happen that I think are really bad. Number one, you aren't actually giving autonomy to your team, and that means that they're less likely to feel ownership over the work product or the outcomes. And so if you start with vulnerability, let's just say with your executive team, you're sharing with them how hard it is to do fundraising or how you have to have $1 million in ARR in order to do the next round or how you just lost your most important customer and it's gonna be absolutely critical to win at least 3 customers to make up the lost revenue that you have. You know, whatever that is, those are all forms of vulnerability. And when you share that openly, vulnerability doesn't mean that you don't have a plan or that you don't believe in your ability or the team's ability to be successful. It just means that you're being open and honest and sharing what is going on for you, the fact that you are human, that you have emotions, And that you have some concerns. If you can do that, then you can start to take the challenges that face your organization and have them owned across your team, instead of taking all of those in, owning them yourself, coming up with a solution, and then assigning out the work. When you do the former, you get people that are connected to the solution. You get better solutions. You get people that feel better about the work they're doing because it's their own and you improve culture. And so this is about finding kind of good autonomy. I think good autonomy starts with alignment around the outcomes that you're collectively targeting and it allows people to figure out the details of how they get there. Bad autonomy is, hey, everyone should just go and do whatever they want to do. The chances that you all land within the target zone or that you're working collectively towards some shared outcome are incredibly low if you approach things in that way. And so, I think a culture of vulnerability around what it is, and vulnerability could be stated as just sort of like the truth about what it is that is required and the fact that it's going to be hard and how you feel about that, and sharing that with your team and expecting them to show up with answers and with solutions instead of just to do the work that you give them. Teaches them to think for themselves and to own those solutions. I think that's the best way to grow and scale a company. And I think it's the way that people feel most excited to be part of that company. And I think it builds the best culture. I don't have all the answers. Maybe there are some leaders that do have all of the answers around certain things. But at some point, I think you break. At some point, you go outside of your genius. You go outside of your area of sort of core knowledge. And at that point, you have to share in the struggle, share in the challenge of what you're trying to accomplish. And that's where I think being vulnerable and open, if you've hired the right people, is absolutely critical and results in the best teams.

That's really well put and I totally agree. Another variation on the same question is, in a more competitive labor market where it feels like employees have more flexibility or more leverage in being able to work where they want to work because of remote work or work when they want to work, partially also because of remote work. or even work at companies that have the same beliefs and values that they have and more the company kind of being customized to the employee in some capacity. And at the same time, there's maybe sometimes that come with that is potentially, at least as it relates to remote, is trade-offs around cohesion. Because if everything is being customized to individual employees, if they all have diversity or different sort of interests, ways of working, styles, wants, etc., values, And that can be challenging to get on the same page.

Yeah. I think it's really hard to recruit and yet every company does it. And I think it's a mistake to— again, this kind of goes back to the very first question of when do you compromise and on what do you compromise? I think the best way to successfully recruit a team and build a successful company is to work on something that's really amazing and inspiring. and to do a good job at it. And success is probably the number one recruiting tool. So if you can make your company successful and you're bringing people into this exciting rocket ship that's taking off, that's changing the world, that's doing something big and audacious that you're just so pumped about, and every person they meet in the company is so pumped about what they're doing and their role and contribution to that, and you're talking about the ownership this person can have and how they can contribute to that success, I think that's your best shot. I don't think you should say, well, we really believe in having driven people that want to work hard and believe in this mission. And they're like, no, I don't really care about what you're doing, but this is the highest offer I've gotten. And so I'm going to accept it. I think that's the time to slowly back away. And again, even though you may be working on that and going, oh man, I've been working on this role for 3 months and I needed this person 6 months ago, I think you have to be honest with yourself. How much pain is that going to create as you build and operate your team when you have someone that's just totally misaligned with your values or the way you work or the outcomes you're trying to drive as a company? You're just going to get so much less out of that person and they're going to be less happy organically. You're going to have to start building these totally artificial incentive programs. Whereas in a company that's aligned around what you're doing and the success of that thing, you doing things to make the company successful is its own organic motivator. And so, you can actually have work and ownership be the motivator for employees as they go through their career. And in my experience, that is by far the most scalable, available, and reliable form of motivation. It's better than compensation. It's better than titles. Ownership and autonomy so that people can do incredible creative work and understand how that connects to an outcome they care about is by far the biggest motivator.

Yeah. In terms of the secretive to transparent side, some companies are more siloed or secretive, some companies are totally transparent. Buffer was even publishing the salaries of what people make. Are you much more on the transparent side or how do you think about information that's good to share versus information that's not good to share?

Yeah, so I've thought about this quite a bit, and I do think there's such a thing as bad transparency. My friend Mathilde, who runs Front, she has a quote on this that I think is exceptional that I have commandeered and used quite a lot. And it's that there's good and bad transparency. Good transparency answers questions and creates trust and ultimately reassures people. And bad transparency raises more questions than it answers. And so I think about that where if what you're going to communicate just results in people being more confused or having more questions, you haven't really acted in service to the organization. Maybe you're not ready to communicate that thing yet. And it's okay to communicate something and say, hey, this is happening and we don't have the answers, or I don't know what to do about it. And that can be really good. And I think that we did a lot of that during COVID not knowing exactly what the future would look like. And when you do that, you're being vulnerable, right? You're saying, hey, I know that sometimes people look at me and expect me to have all the answers. And right now I don't have the answer, but I'm going to be really open about how we're thinking about it. I think in those moments, if you don't know the answer, you need to have a plan. You need to talk about what the next steps are, how you're going to get to an answer. And in other cases where you do have the answer, you're communicating about something where basically people are probably creating their own narrative. It's something that's confusing. It's something that is creating more questions. And you're saying, hey, this thing is happening. We're noticing this. We're hearing this. And I want to communicate openly about what's going on and what we're doing about it. And so, I think it's important not to just say, Hey, I'm the CEO of the company and anyone can just read my emails. Anyone can just, you know, read the notes from the leadership team and exec team because not everyone has sat through those experiences and not everyone has kind of the stomach for it. Certainly, I imagine if most employees experience what it's like to do fundraising where you collect 99 nos for every 1 yes, I don't know, around no 20 or no 25 or no 30, they might start to doubt the company. And their ability to raise funding. And if they did and they decided to leave the company, that would be a mistake if the company then at Answer 100 got the fundraising round and it was totally fine. And it's probably because that employee's never done fundraising and doesn't have the stomach for that or hasn't learned that yet or hasn't learned that information. What I think is awesome is when you get that term sheet and when you raise that money and you close around and the money's in the bank, you go back and you teach that lesson and you say, hey, I'm really excited we raised this round. If anyone's interested in what it's like to raise money and in how many nos you collect and what process you go through, we're going to do a lunch and then we're going to talk all about it. Like, many of you are probably going to be founders at some point someday and like, you should know how hard it is. This wasn't like I showed up for a meeting on Monday, I got a term sheet on Friday, I had 3 meetings and we just closed our round. Right. And so I think there's an opportunity for that transparency at the right point in time. When you have answers, when you can clarify, when you're not just introducing concern and mistrust and doubt into the organization.

Yeah, that's really well put. I was reminded Peter Thiel apocryphally had this philosophy at PayPal that every person can only work at one thing at a time and it has to be a big thing that they crush. Is that correct? Are you familiar with that? And I guess how do you think about— I just say it as a segue to ask about The trade-off between focus and people being able to do multiple things?

Yeah. I think that sometimes these sayings and these truisms get simplified or boiled down into an idea that might be more pointed or more narrow than the original intention. So I interpret that intention as, hey, you shouldn't be working on 10 different big things at once. There's just no way you're going to do a great job. Can you work on 2 versus 1? Kind of depends on the person. I don't think that there's no person that can work on 10 things. I mean, interestingly, Peter runs how many companies all at once and they're all important? So like, I don't know that that's true. Like, Elon's running how many companies? So I think that sure, there are certain people that can do many important things at once, but the lesson is probably more that we generally are trying to do too many things. we could generally cut things off. And we will die by mediocrity of middling ideas if we're not careful about those. And so we have to be really careful, particularly with ideas that are okay but not great. Those tend to take up all of this space. And in venture, you learn the same thing, right? Like, you invest in 10 companies and you will spend a disproportionate amount of time with the ones that aren't that great, the ones that are failing versus the ones that are really successful. And if you look at the power laws, then you actually should have been spending that time helping the most successful company recruit the very best people versus helping the company that was ultimately going to fail to get to the next day because they need your help actually just to get to tomorrow. And so I think the same thing is true in companies. You have to think about there's gonna be a handful of things that make or break the company. Making sure that those things go well and are successful is the most important thing you can do. You can spend a lot of time and energy kind of checking every little thing and moving 100 different initiatives one little step forward. But at the end of the day, like, it's not 100 different initiatives that are going to make or break your company. And so I think understanding, being ruthless about prioritization, understanding what the key things are for your company to be doing and getting that list down to like 3 to 5. across the whole company is really important. And then having each person in your company understand like what are the 3 most important things that they are working on over the next X period, that's really important because those things ultimately contribute, right? They're connected. This should waterfall. This is, you know, maybe we'll talk about OKRs, but this is basically my belief around having those OKRs waterfall. You're talking about the building block, the building blocks. And so in a car, there's a million pieces that make sure that the engine can convert the gasoline to energy that makes it move forward. But if you think about what's the most important thing for the car to do, you're like, well, it needs to go and it needs to stop. They're 2 really important things. And how it goes is the details. It's like the OKRs. What are all the little contributing factors that need to go into that? And so I think as a guiding principle, how do you go from the 100 things you might be thinking about down to 3 to 5, down to what's the most important thing I need to get right today, this week, this month, this quarter, this year? I think that's a good— Yeah.

Let's segue back to our annual plan topic. What's the key to get right in creating a great annual plan? Or put another way, what mistakes or misconceptions do people have when making it or thinking about what makes a really great one?

Yeah. So your annual plan is just your roadmap for how you want to get to a given outcome. And some people do this with OKRs. Some people do this with other tools. Those things are all just tools and they're all generally trying to do the same thing. You're trying to say like, okay, well, we should take some time thinking about what's important, making sure we're on the same page about that, debating that. So in case you know something that I don't know, that we're sharing that information and then getting alignment around what's important. So when we come out of that annual planning, We have a sense of where are we trying to go? What are we trying to achieve? We start to dissect that into a timeline. For an annual plan, it's a year. And so we say, okay, what do we think is reasonable that we could achieve this year that contributes to that big audacious thing we want to eventually achieve? And then you start to break that down into this quarter. And what can we achieve this quarter that supports what we're going to achieve this year? There's often a lot of disconnect. Around each of those steps. People may be disconnected around what you're trying to achieve long-term. This is where you're recommunicating around that culture, what's important. Have we learned any lessons that change how we feel about the long-term future of the company and how we're going to get there? Great. Now is a good time to surface those. Now is a good time to, like, solidify those, get on the same page about those. Maybe it's at one level down. Maybe it's, hey, our 10-year vision is the same, but we turned over some new leaves and learned some new information. We thought we were going to be able to do it by doing X, and it doesn't make sense for us to do that anymore, and here's the reasons why. Maybe a third party comes and builds that tool so you don't need to build it in-house. So instead of spending 6 months building an EHR or a year or 2 years doing it, you know, you can use this off-the-shelf solution that didn't exist last year when you made your annual plan, right? So there's new information, new tools that are coming about, and The annual planning process is your opportunity to factor in new information and learnings to decide what is the best use of your time over the next year to achieve your ultimate vision or goals. When you create your OKRs or whatever tool you're using, they are simply to bridge between the outcomes you desire and the work required to get there. There are 2 things that I think people have to think about. The first is you have to be able— it's going to sound like sort of simple, but you have to be able to communicate the work that needs to be done. If you cannot clearly communicate what is required, how the hell is your team going to get that work done? How the hell are you going to get on the same page with everyone around what needs to happen? So sounds kind of simple, you know, but you have to be able to clearly communicate the work that needs to be done. The second is that you have to define the work for the time period. So if you are setting semiannual OKRs, semiannual every 6 months, if you think about a project and you're like, yeah, this is a 2-year project, but let's set it as a 6-month OKR, you're just setting the team up for failure. You know it's a 2-year project, you know it's not going to happen in 6 months. That's the wrong way to be ambitious. If it's ambitious to get it done in 2 years, then what is the ambitious component that you can get done in 6 months? And the biggest mistake that I see people do is they get really excited about the outcome, sort of disconnected from OKRs. And this is why it's so important to have time around OKRs. Some elements within your OKRs, even for 6-month OKRs, could be, and in 1 month, we're going to deliver X. You're trying to breadcrumb and do the building blocks of how you're going to get to this. And you're building these objective checkpoints to say, did we achieve this thing? That planning process allows you to answer the fundamental question of, did we not achieve our outcome at the end of the year because we didn't do the right work? Were we wrong about the strategy, right? Did we say, let's do X, Y, and Z, we did all of it and it didn't work, or did we not execute? Those are very different. And it's really important to understand as you're leading a company, if your strategy was wrong, you probably need to shift your strategy. And I think too many people make this mistake of they don't define the OKRs in a reasonable way, the work doesn't get done, and then they don't get to the outcomes that they would've if that work had been done. That is an execution problem, not necessarily a strategy problem. And so you have to think, is this execution or strategy? And these tools are just a way to write something down that keeps you honest and holds you and the organization accountable around what you're trying to achieve and how you're going to get there.

And so, do you know why Keith doesn't like OKRs or he says he doesn't like them until you have a monopoly?

Yeah. OKRs have limitations. They are just a tool. Having them doesn't mean that you've created a successful company. if you're achieving your OKRs and you're not successful, then your OKRs were probably bad. That means you did the wrong work, you had a bad strategy, you weren't being thoughtful enough about what the work was that you were doing. I think Keith definitely believes in communicating about the work that you should do and achieving that and having that work towards your shared goals. I know he does. I've worked with him for many years. I think that when people get so grounded in their OKRs, that's all they focus on. And when the OKRs become an exercise of creating kind of tactical execution-oriented tasks that make you feel like you're achieving success independent of the outcomes, that's when they become a problem. And so I think it's more that there are just lots of bad OKRs in the world. And spoiler alert, before OKRs were a thing, there were lots of bad goals out in the world. You can absolutely manipulate OKRs. You can absolutely set these up in a way that doesn't really help you. And so I think the thing to keep in mind is to separate your efforts or inputs from outcomes. As humans, we generally want to work on things that we ultimately consider a success. Otherwise, we kind of feel like we've wasted our time, right? And that's really important. The reality is that your team can do an exceptional job executing, and that's the inputs, and they can still be unsuccessful at achieving whatever outcome that you set. I think that this is the challenge. This is where we get emotional around connecting those 2 things. So we need to separate those. We need to be able to have an honest conversation about if we should change course. And it's okay. You might want to have the same employee do the same type of work, just in a different direction to achieve your outcome. And so I think that the people that don't like OKRs most often don't like it when people blend these 2 and you start to enculture this idea that, yeah, you did the work. You shipped those 10 emails you said you were going to ship and you hired those 3 people and you did this. But spoiler alert, we weren't successful. And so this is where you have to have that conversation about execution versus outcome. And that would mean that your OKRs weren't the right OKRs, right? And so there has to be ownership around that. And so those— that's why it's so important that in your objectives, you're talking about the outcomes you're trying to achieve. Even if you've done every key result and you've hit it out of the park and you've done it ahead of time, ultimately, you hold yourself accountable. Did we achieve the outcome? And if you didn't, You failed your OKR.

Yeah, that's helpful. I want to segue into building an executive team. We were talking about hypergrowth before. A company raises a seed, they raise an A, maybe it's 2 co-founders, they're growing, they've product-market fit, and now they need to build an executive team. We're going to go through some individual roles, but first I just want to get your sort of high-level philosophy or frameworks or what's important to really get right. When starting the process?

Yeah. So I think the most important thing is to orient around outcomes. And so I start by thinking about what is the work that we need to do or the work that we need to figure out. Maybe we don't even know it yet. Maybe we don't have a finance background and we know we need to hire a VP of finance, but we don't actually even know what the work is that they need to do because that's not our expertise. What is the work we need to do or the work we need to figure out to achieve our outcome? And maybe the outcome is the next step, the next stage, like something that you want to go to as a company, or maybe it's a specific deliverable that you have or an accomplishment that you want to have. And when you're hiring executives, there's a bunch of different types. You may need an executive to be more or less of a functional specialist or expert in their area. You may need them to be a visionary. You may need them to be a great people manager. You may need them to be an amazing spokesperson and really inspiring for your team. You might need them to be a talent magnet. That really depends on you and your team. And to some extent, that also depends on what— where your gaps are. And so the first thing I would do is kind of look inward. Look at yourself and look at your existing team and ask yourself, like, where are we not yet great? Where do we need help if we want to build the type of organization and team to be spectacular at these different things? Do we need help recruiting talent? Do we need people that are going to be cultural magnets, that are going to be incredible spokespeople inside our company? Are we not great at management yet? Do we need people that are really going to guiding lights to that and be exemplary citizens around what it's like to be a great manager and going to instill that and teach all of us that, right? So you have to figure out what it is that you need beyond just the function of the role. And then you talk to people. And so I want to hire people that are better than me. That's why I'm hiring them, right? So I want to find the person that inspires me about what the role could become. I've definitely had this experience where I've walked into a conversation expecting X and walking out with like X plus Y, Z, A, B, C, D. Like had no idea that this person that I was thinking about for a marketing role was also just going to be such an amazing spokesperson and just like so much energy that I could feel it in the room that they were going to have all these other positive effects in the organization that it felt like they could. And so I think you want to walk into that with an idea of what you're looking for and then look at what are the extra things that you might get and do they inspire you, right? This is just like when you're dating somebody. You might go into a relationship with an idea about what you want or what you need. And what I find is generally you date people and it turns out some of the things you thought were must-haves, maybe you could compromise on. And maybe there's other things that you'd never thought about and it turns out those are really important to you. And if you break up with that person, suddenly those are must-haves in a future relationship. And so I think you can learn a lot in those conversations. Generally, when I'm looking at executives, there's a few things that I'm looking for in every role. I'm looking at their cultural fit. How much are they going to fit with the culture that we have, the culture that we want to have, and where are there going to be rubs? Where do I think that just like, hey, there's these things culturally that are not things that I want in the organization. and they seem to be true for this person, how much are they willing to change? Are they really steadfast on that? When you find that you're digging your heels in opposition, those are the really big pain points that I think you need to be careful around. The second is around creativity. You're going to bring a lot of people into your organization, and especially as you scale, the biggest tension that I see is with experience versus raw ability. And so, there's a time and place for experience. There's nothing that can really replace it, but you have to balance it. If someone has had so much experience that they think they have it all figured out, like, what is their attitude about their experience, right? Do they think that just because they've done it for 10 years, they know all the ways and the perfect ways and the right ways and that all the ways you're doing it are wrong? How do they come into that conversation? Do they have curiosity even around something that they're an expert in? Like, we should all be in that growth mindset. And how creative are they about problem solving? You know, can they take on things that might sit outside of what they've done in the past? And then the last thing that I always look for sort of across the board is motivators. What are the things that get them out of bed? Why are they having the conversation with you? Why is it that they're thinking about leaving their current role? What inspires them? And do I believe that in this role and with me as their manager that I can continue to motivate them in those ways, that that stuff is going to be available to them? Sometimes the answer is no. If somebody is coming in and they want to be your CFO and they're interviewing for VP of Finance and it seems like they really want to be the CFO, but you're just not offering that to them, and maybe you have a CFO and that CFO is not leaving, you can't give that to them. And if that's their motivator, if it's like this title and role, if you can't give that to them, you've got to be honest with yourself. And at 6 months or 12 months, someone else is probably going to come along who can give that to them and can motivate them in that way. So you have to figure out in that conversation, is that going to be a make or break? And if so, you got to be honest with them and see if they're still motivated to join.

Yeah, that's awesome. I want to go through some of the individual roles and I'll start with the one that you most recently did, which was COO. As you build out an ops organization and as you look for a leader, what's really important to get right or what's your framework there?

I think you want to go through a bunch of different roles. So I'll give you sort of a few thoughts on each of these, but probably won't be comprehensive. The first one when I think about this, is what I would call big company-ness. Oftentimes when people are hiring a COO or head of operations, I've talked to probably over 100 founders at this point that want to hire folks for this role. They are trying to grow up. They're trying to hire an adult in the room, if you will. I hear this kind of terminology a lot. And there are lots of different types of people that come into that. Sometimes people come in and they want to take the 100-page process and operations manual that they've created at their 10,000-person company as a director of operations or a VP of operations, and they want to just take that and apply it to your company on day 1. I would call that fairly big company in terms of their mindset and how they approach that. So I think you want to see, and this may be true for all roles, is sort of How do they operate from their place of experience and knowledge and the current place that your company is in? Are they thoughtful about building that bridge between those 2 points, or do they plan to come in guns blazing? And to be honest, in my career, I've come in too guns blazing at certain points in time, and I've gotten that feedback and had to adjust and go, okay, yeah, you know, even if 20 other companies do it this way, even if it's the best practice and, you know, it's broadly accepted, you have to understand that when you come into a company and you affect change, someone else often who's still at that company thought that whatever you're getting rid of was the right way to do this thing. It was someone's idea. Someone thought that this, this was the right way to do it. And so you have to be thoughtful about making those changes. It doesn't mean you don't make the change. It just means that you're thoughtful and aware as you make the change and you think about where is the company today? What is the state of that company? What stage are they in in their growth? And how do you take the information that you have and apply it to where they are at that moment? I think you also want to look at people's proven abilities. If you are hiring, particularly as you go to executives, you're kind of hiring for an existing capability. I would say that Raw horsepower starts— if you think about a line graph, the more junior a role, the more you're willing to hire just for core raw horsepower and experience might be less important. The more senior the role, the more you kind of want to index around, hey, can this person do this thing? Have they proven that? Do they have an ability to scale and evolve operations, teams, processes, policies? Right? Can they come in and morph and change with the company as we grow? Have they done it before? How did it go? Right? What would the people that were in those organizations who saw them do it, what would they say about it? Do I want that to feel— do I want it to feel the same way here with however it felt there? Right? How creative is this person? We talked about creativity for all roles, but specifically for an ops role, when you go into something that's a little bit more process-driven, Can this person kind of like pause all that they know and break it? Because maybe there's like something that needs to change. Like, how creative can they get around taking what they know and applying it to your organization in a way that fits the culture and fits the stage of where you are? And then lastly, like, what are the scale of the problems that they solved? And are you hiring ahead of where you are? So have they worked on problems that are at least as big as the problems you're facing, but ideally problems you think you will face in a year, 2 years, 3 years, so that they can continue to be the right person for this role versus being an amazing fit for the role today, but believing that in a year or 2 years you're going to outgrow their capability. So these are just some of the things I would think about specific to operations.

How about just that last point more generally when hiring? Like when you think, hey, this person is exactly what we need right now, but at our hypergrowth, unlikely to be what we need 12, 18 months from now. Do you tend to think wait until you find the right person that you think will scale, or how do you just sort of think about that generally?

Yeah, so I think there's 2 different ways to think about it. One is you go back to some of these other elements around capability, your belief in their future capability. So maybe they are exactly what you need today, But maybe they're growing really quickly. Maybe when you look at their resume and their past history, they weren't what you need today 6 months ago. And man, they have just had an incredible ability to step up to the plate and take on more and grow and scale. Like, I want to invest in those kinds of people, right? So maybe they're a perfect fit today and maybe they will continue to scale because you look at what they've done and you believe in their ability. You start to test them around problems for the future. And they, even though they've never done it, they have a really good ability to adapt and change and move into that. And then the second thing is you check in on those motivators. If they're really motivated by position and title and role, then what happens if in a year or 2 years you need to level them? You need to hire above them. Is that going to be devastating? Are they going to take that with a grain of salt? Right? It's hard, even though we know that as our companies scale, the exact same role becomes bigger. When you're standing on that slice of pie, it doesn't feel bigger, right? Your title hasn't changed, and it's happened so slowly. It's like watching a kid grow up, right? Like, a 4-year-old doesn't realize that they have grown up so much when they're 5, but when you haven't seen them in a year and you show up, you're like, oh my God, What's happened? And startups can feel that way, right? Your marketing team that used to be 5 people is now 10. It's doubled in size. Your product team, which used to be over one feature, is now covering 3 different product lines a year later. The person running product has a much larger role, but they're still called director of product. And so I think it's really important to constantly be checking in and communicating about that so that people feel their role getting bigger. They understand that even if you're standing still, if you're standing still while kind of the earth under you is expanding, then that land you're standing on is much larger. That responsibility is bigger. Your role has expanded. And so I think that's what you have to think about as a company. You can do this with compensation. You can communicate like, hey, you are making progression and separate that out potentially from title. But this is where you have to understand the motivators. And sometimes you have to have really difficult conversations where 2 years later, this person was a perfect fit 2 years ago, 2 years is a long time to have somebody that's a perfect fit. That's awesome. And now they're not the perfect fit. Is there something that they're the perfect fit for in your organization or that they can become a really good fit for and have that difficult conversation with them? So I don't think there's just like an answer to you interview someone. I think if you're 6 months into interviewing for a role and you haven't found anyone that can go way above and beyond and you find someone who is a slam dunk for what you need today, If you can have an honest conversation with them about how you imagine the role will grow and how you're excited for them to grow into that, but there's a chance that they may not, I think that's an honest conversation with them. And then you explore that when you get to that point and you see whether or not they were able to grow into it. And if not, you make a change.

Yeah, that's fascinating. Let's go into revenue and building revenue org and looking for a revenue leader and a CRO.

Yeah, so I think some of these same things apply. Like a CRO, for example, is one of the last executive roles that most teams tend to build. And so you're really generally at a very different place in the maturity of the company. And I think you have to look at what exists today in your revenue org. In many companies, the sales team was a set of people that have never done sales before. that were testing out sales and now they're doing sales. And you probably already had to face that problem because when you hire a CRO, you probably already have a VP of revenue or sales. You probably already have one or more directors, right? So you start to mature as a sales or revenue organization. If sales is how you're driving your business, probably is if you have a CRO. And so you have to think about where are the gaps? in that sales organization? Why are you hiring a CRO? Why is your VP of sales not enough? Like, what is the gap that you're trying to fill for? And so that helps you answer the questions of, is this CRO actually supposed to really be a visionary around what's next? Or, you know, is what's happening now really working? And are you really wanting that person to be an operationally excellent person, right, who comes in and they just make what you're doing 10 times better because they've done it at a much greater scale. But there's very, very different roles for CROs. And I think a big one is around that. It's like, how much of this is like a souped-up VP of sales that's really focused on the funnel and driving outcomes? How much of this is a person to kind of imagine the future of revenue at your company, the new ways that you're going to make revenue, the new ways that you're going to set up subscriptions or build customers or change your sales funnel? Like, Are they really imagining the future or are they making what you have today just so much better? And so I think a lot of things around the head of operations also apply to your CRO. The other thing that I think you'll tend to see around that role is an importance around compensation. So that's probably going to be your highest paid role at the entire company. It probably makes more money than your CEO. That's a cultural change that a lot of companies have to make is this idea that Someone is coming in who's used to getting paid, oftentimes cash bonuses immediately or very closely aligned with their performance every 6 months or 12 months. That's very different from the general comp philosophy at most startups, which is, hey, you're getting paid well, but you really share an equity around long-term connection. And so it requires a little bit of a shift to being comfortable with like, hey, this person is more short-term motivated around compensation. How do I get them to stretch? Because we're not a public company, we are a startup and we want them to still be motivated around equity and longer-term things. How do I get them to bend a little bit on that so that it's not just them leaving a big public company, coming to us and expecting the same compensation? But also, how do I accept that this is the area they work in, this is normal for what they do and As a company, we have to also probably flex a little bit into that. They have a lifestyle, they have certain things they do, they've built their life around being in this role, having a certain comp. And so that's the other thing I see startups struggle with most around sales more broadly, and certainly around a CRO, is this real change in culture of compensation and how they think about that. And then how much do they want that culture around the sales and revenue organization to be the same as the culture that they have for the rest of the organization? How much do they want that to be insulated? And how much do they share in their beliefs on that with the CRO who's gonna have a lot of responsibility in making sure that that's maintained?

Yeah. And let's go a layer deeper. Before the CRO, talk about what to look for in marketing leaders or sales leaders and just building out marketing teams and sales teams. And maybe you can throw in BD if appropriate.

Sure. Let's talk about marketing specifically for a moment. I think the biggest one is to think about brand versus performance. If you're not a marketer, those terms may not even mean anything to you, but effectively brand ends up being creative development around who you are, how you are, and communicating that out to the world in a way that tends to be a little bit less data-driven. And performance marketing tends to be around driving specific outcomes in the near term, trackable specific outcomes. So examples of this would be, you know, Nike running a Just Do It campaign and it feeling great and people seeing that and like having better feelings about Nike versus Nike's performance marketing campaigns, which are, hey, we're going to try to get 100 people to buy shoes this quarter. What campaigns can we run and which ones are being effective and how much is it costing us to acquire a new customer to buy those shoes and is it working out? Most startups are hiring performance-based marketers and they need to be really careful as they're interviewing marketing leaders to understand their ability to do performance marketing versus brand marketing. Can they sit across both? How much experience do they have with each and what is their default? How oriented are they around performance marketing metrics And does that line up with you? Are you going to just be frustrated and disappointed and confused about how they're spending money and where they're investing their time because maybe you are super performance-oriented and maybe they're not? And so I think that's a really important thing culturally to figure out with marketing. The other is the breadth of their ability under marketing. Marketing could encompass comms, it could encompass your brand strategy, it can sometimes encompass design, it can encompass your performance marketing. It could be around creative content development if you have a blog or personality, social media, right? So understanding what these people have done and how much that lines up with what you need them to do today and what you imagine that growing into is really important. And then the last piece I'd think about on this, which applies to marketing but also more broadly, is their data orientation and understanding. They might have worked in an organization that is not super data-driven. If you're a very data-driven or data-informed organization, it's really important to have that in common with your executives. It's true across all of them. Tends to be that VPs of finance and heads of ops are more naturally data-oriented. You know, they are living in spreadsheets and they're used to reporting out on what they do in a very data-forward way. Some heads of marketing do that, some heads of BD do that, some heads of people do that, And others don't. They're just not used to that culture. And there's not a right or wrong way for this, but it is important that you're on the same page. Otherwise, you're gonna find yourself being very frustrated or having to train them on this. And it's a cultural training. It's really deeply embedded. And it kind of goes into like, what is success? How do you define success? And so I think that's something that you want to be aligned on very, very early on. Specific to BD, the one other thing that I would say for that is you want to understand how the BD people think about success. Do they associate getting a deal done with being successful? Are they kind of like a quantity volume of deals done type of BD person? Or can they sit in an environment where it's like, hey, we're trying to build partnerships, lots of partnerships are the wrong thing, they distract the organization, they take up resources, and very rarely do BD deals go as well as you hope they go when you're imagining them in your mind and doing the initial deal. So is this person comfortable with that? Are they comfortable getting deals all the way to the finish line and then killing them because they're the wrong thing? Are they comfortable going 6 months without getting a deal done because it's not the right thing for the organization or because the organization doesn't have the resources to support it? Are they good at communicating with the rest of the organization to make sure that the deals they're getting done are supported by the organization that is going to need to support them in order for them to be effective. It's these kinds of things to make sure they're not just going out and doing deals for the sake of it, and that those deals that they do, the work that they do, instead of it causing a cost to the organization, it's something the organization is ready for and wants and needs so that you can use those to drive the business forward.

Yeah, that makes a lot of sense. I want to segue over to finance. Keith also has this framework around value preservation versus value capture in hires. Value preservation, you want to hire for experience. Value capture, you want to hire for slope. I'm curious if— I think Keith says for many orgs, CFO is often a value preservation role. One, does that construct resonate with you? And then 2, what to look for in a CFO?

I've experienced both. So I've met with lots of CFOs that I absolutely think are view their role and are comfortable with their job being to keep the trains running on time, to make sure that the reports go out and to make sure that you're in compliance. And a lot of HR leaders are like this as well. They think it's their job to make sure that you're compliant and that you can hire in different places and that you can send your paychecks and you can execute on the things that you need to do. And so again, this is about mapping what you're looking for for this role to what this person is exceptional at? To what extent are they trying to keep those trains running on time and preserve the value that you have? And to what extent do they really imagine punching through the ceiling and doing things in a new and innovative and different way? How consistent is that with what you want and what you need? If you set up an amazing organization, if your finance organization is closing your books really quickly and they're on a modern stack and your board is always really clear about how your company is doing financially and they're going out and getting, helping you get lines of capital and it just seems like all engines are moving and you're hiring a CFO because you want to take the company public and you just want to expand the team, you're probably trying to preserve a lot more of what you're trying to do and add in a set of skill sets around experience, like specific experience, for example, like going public. And that's probably what you're looking for. That's very different than if your finance team is broken, you've been using an outside accounting firm as an interim sort of finance operation, you're struggling to close your books, you're often having to go back and amend your reports, your board is always asking questions that you can't answer, you're struggling to recognize revenue, you're running into all these tax issues that you didn't plan for, that you're being really reactive instead of proactive in your planning. then you're probably looking for a CFO that can reset the team, right? That CFO needs to be able to uproot, rebuild. You know, they need to have a strong opinion on things and a viewpoint of how to get those things done. They need to be coming with a set of people that they can bring, right? It's a very different skillset. And so I start with like, what are the needs? I think functional expertise is probably most important in these roles. In a VP of finance or CFO, you're often hiring functional expertise. There's just a lot of compliance and a lot of components that you can't replace knowing how to do SOX compliance. Like they either do or they don't know how to do it. And if that's what you need to do, that's what you need to do and you have to own that. I think about the current ceiling versus the potential. So if you're hiring a VP of finance, what are their aspirations? This goes back to that motivations things. Do they want to be a CFO? Do you think they can become a CFO? Is that the reason they're joining your company or is it not, right? Like, what are their aspirations and is it what you need? And the 2 other things that I think are really specific to finance, one is what is their appetite for risk? I see many people in the finance roles that perceive their job as looking to tell you no And I am looking to understand how. This is also very true of GCs and heads of legal. If you want them to tell you when you're like, Jared, you're crazy, don't do this, like you're going to get us arrested, absolutely, please tell me that. But when there's something that we could potentially do, I want the default position of these partners that we work with that sit between us and the law, that sit between us and compliance, To say, oh, well, that's not normally how people do it, but let me think if there's any way we can do it. I want them to approach that with curiosity versus defensiveness. And so that's a really important thing to look for in legal and finance roles. And then the last thing, which is true for both of those roles as well, is your level of trust and perceived confidentiality. So this role And your head of HR or head of people roles, they have access to so much information that no one else has access to. There's different access for your finance team versus your HR team versus potentially your legal team, but they have access to a lot of very privileged, very sensitive information. They understand what's going on at the company. They understand when bad things are happening at the company. They understand what people are paid. They know what all of their teammates are paid. You know, they understand, they work in a different space in terms of access to information. When you're going through fundraising, they know that you've been going through fundraising for 6 months, whereas the rest of your company may not know that you've been doing that. And so they may feel like it's not going very well. And so it goes back to that, hey, is everyone prepared? Is everyone trained? Is everyone comfortable with the idea that it might take us 12 months to raise funding? You know, like, if they're not, then somebody in your finance team may start to get a little uncomfortable at month 6 or month 3, or maybe they're really unfamiliar and 30 days in they go, oh my God, why have we not gotten a wire in? Like, I saw the deck that went out, we worked on the deck a month ago, right? And so it's about setting the right expectations and managing that transparency that they have. So you need to make sure when you're hiring for that, this is a person that you perceive will be totally confidential with that information and that you feel an incredible sense of trust with them because you are giving them keys to the kingdom in a way that you aren't as much in many other roles.

Yeah. How about people function? The right VP of People or Chief People Officer, just that function in general. What's really important to get right or what mistakes have you seen?

Yeah. So all of the things that we just talked about that are true for this function as well apply. A couple things I would say on them specifically. One is, what is their orientation around how they scale? Do they scale through people or technology? Do they just throw more people at the problem, or do they tend to look towards technological solutions? And the reason why I say this specific to the people team is that they are sitting around people. They're their skill set, they're often running your talent and recruiting team. And so they may be disproportionately inclined to solve problems by hiring people. And so I think it's something that you have to be careful about. This is like a surgeon is disproportionately likely to recommend an operation because that's their skill set, right? And so I think you need to be thoughtful about that. If the right answer is, hey, there's actually some technology, some system that we could use that would cut the amount of work this thing is in half, and they don't know about it or they're not inclined to look at it, they may think, well, I've been in 10 different organizations, especially if this is a really senior, very experienced people leader. I've always hired HRBPs for every 100 new employees we hire, and so we should hire another HRBP. They may be minded in that way, and I think you just have to see how curious they are and how much they've been able to adapt and change their perspective. The second is this person who runs your people team is going to be deeply embedded in the culture. They're going to be your eyes and ears often into the organization. They're often going to hear the early warning signs of problems, and you want to understand how they're going to react. So I think you need to align on your beliefs about how the organization should be run. And this is where you have to look at, okay, What are the roles of values? When different issues come up, how do I think we should react? How do you think we should react? And check for those moments where you're both dug in and not on the same page, right? If they think that when an employee has a complaint that you should address it at an all-hands and you just think that's totally inappropriate, you should look for those things. You should try to understand, like, what— where are they feeling really strongly and where do you feel really strongly? If you're in opposition on that, that is foundationally about how you run the company. All the rest of the stuff doesn't matter. It's just not going to work. You're going to be frustrated. They're going to be frustrated. At some point, you're going to start undermining each other. It's going to be really bad. And so you need your head of people to either be on the same page as you or inspire you to be on the same page as them in how you're going to run your organization. And you want to see that they have flexibility and curiosity around how to do that better and differently over time versus again, kind of taking that handbook that they might have developed at 1, 2, 3 other organizations and coming in and just starting to copy and paste that. I think that adaptability is particularly important in this role and you have to be aligned with how you run the company. Otherwise, it's just not going to work out.

You've worked with some really great leaders. We mentioned Mads Levchenko, we mentioned Kritra Boy, Jack Dorsey, many others. I'm curious, what's a takeaway that you have in common with some of them at Earned Secret and what's an Earned Secret that perhaps you differ?

Yeah. Well, I'll tell you one that I think has become a truism and I think is definitely true for all of those leaders is that recruiting is just absolutely critical. Having exceptional early employees will fundamentally change the trajectory of your company. And I think that when you think about those individuals, if I was to reflect on thinking about this from like an investment standpoint, if I was only to invest in exceptional founders, the returns of that portfolio would massively eclipse compromising on that variable, right? If I was to compromise on that and you say, yeah, but it looked like a good business or a novel solution or it was a popular idea, that would pale in comparison as a criteria for investment success and the ultimate success of those companies. So I think that you want to invest in incredible people. Part of that is because you can trust them to do more, right? So I broadly subscribe to the idea that you should have shared ownership and you need employees to feel like owners and to act accordingly. So if you have exceptional people that treat the business as their own, that tends to result in a quality and speed of work that is unparalleled. And basically every leader I've ever worked with subscribes to that thought. So that is something that is shared. I'll talk about some things that I think are Maybe not shared or not as common. So I've talked about 2 of them already so far today. And one was around transparency. I have my own beliefs on good transparency and bad transparency. Some people share that and some people don't. The other is around autonomy. And we talked about that. I really believe in people having autonomy. I think there's bad autonomy and I think there's ways to think through that in a way that really gets you towards some shared outcome. But I want to talk about a couple others as well. So the first one is something that I actually learned at Square, which is that details matter. And that might sound sort of trivial. I didn't fully absorb that when Jack said that to me at some point when we were doing a review, but it has sunk in and it has come back as really, really good wisdom. And so I want to talk about what that means, because I really didn't learn it until that point. Jack felt really strongly about the quality of our design and even the design and presentations in internal meetings. So at Square, we had people put a level of craftsmanship into some of the smallest details. And it turns out that that has a really big impact. So by doing this, you set the tone and the standard for what work should be, and that really ripples out across your company. So for example, like, you can set the tone that product quality matters by making your all-hands exceptional. It actually just raises the bar. Now, the hard part is that minding every single little detail is probably a mistake that slows you down. So you have to choose the right details, the ones that are going to be high impact, to get those right. But I have seen this work time and time again. to uplevel how people think about what they can put out into the world. And it starts internally. It starts by thinking about how much time and attention do you put into the little details inside the company, and that will ripple out into the products you build, how you communicate, the marketing you put into the world, the code that you write, how you show up in conversation, how you recruit, right? It is a level of care and thoughtfulness that really stands out. It stands out to candidates. It stands out to investors. It stands out to customers. And so I think that's the biggest kind of differentiating lesson that I have learned over time that I think is really different from what I see at many companies. It is actually to sweat the small stuff and to think about how— I sometimes talk about pressure point feedback, like How can you think about pressure point feedback in the organization? Where are there pieces that you can take and make exceptional to serve as examples of what you want to see across the organization? When you link that with autonomy and ownership, and when the people you're giving that autonomy and ownership to are exceptional, then you're taking exceptional people and you're telling them, this is the bar, and they actually have the ability to deliver on it. And they have the power to deliver on it, and you've given them the space and the resources and the time and the agency, they're going to go do amazing things. That is the single best way that you can improve the speed at which you're executing, the quality of your work product, the happiness of your employees, and the overall culture of your company.

That is a great place to wrap. Jarrett, thank you so much for coming on the inaugural episode of this podcast. This has been a lot of fun and a lot of wisdom.

Yeah, thank you so much for having me. It was a pleasure. Always fun to talk, and I'm sure I'll see you in a few years. Exactly. Hopefully before.

Thanks for listening to today's episode. Execs is produced by On Deck, where top talent goes to start companies, find their next roles, or invest in their careers. If you're looking to start a company, uplevel your career, or navigate a career transition, I encourage you to visit beyonddeck.com. See you next time.