‍I. Session Takeaways

Date: March 2024

Executive Hiring: Forming your E-Team

Like your product, your leadership team will evolve with your company. Embrace change.

• The structure and makeup of your executive team will change as you scale and your business has new needs
• Increasingly, this will mean hiring external executives to scale functions where no internal leader is scaling
• As a capable leadership bench is filled, your direct reports will narrow. Most CEOs aim for 5-10 at scale
• Too many direct reports = low focus and less time spent on where you uniquely can drive value

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No “correct” leadership structure. Optimize for what lets you spend time on your strengths.

• No “correct” structure. Framework is to complement yourself with leaders that let you play to your strengths
• Pedro, after iterations, has organized Brex to enable him to stay close to product, design, and customers. 
• This is because he co-runs the company with his President, Karan Anand. Karan runs Engineering, GTM, and Marketing, but he spends most of his time on GTM today. This enables Pedro to spend time on EPD (his strength)

Pedro on Direct Reporting Structure ‍

“The sort of principle that I have with my President is we co-run the company together. I treat all direct reports of my direct reports as my direct reports as well. So I have a fair amount of access [to my CMO and CRO] and they spend a lot of time with me. I probably spend more time with my CMO, for example, than my President [does]. And we tend to be pretty fluid about where we spend time and how we divide and conquer. I spend a lot of time in Engineering, Product, and Design. He's spending more time on GTM these days. They used to be the reverse a year ago. So you know we tend to not let the org structure prescribe too much where we spend time.”

“I think my strengths are typically being close to the weeds in product and customers and I just sort of build a company around that.”

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Hire only when you have product-market fit in a function and will need to scale that team

• Executives excel at “scaling” functions. Typically, they do not excel at “building” functions from 0 to 1
• Bringing an executive in this 0 to 1 phase is high risk as you’ll lose time and end up having to fix the mess
• In the 0 to 1 phase, own the function and support yourself with player-coaches (80% ICs, 20% managers)
• Once a foundation is in place (e.g., function product-market fit), look to hire an executive or promote a leader
• A telling sign of this, per Tony Xu at DoorDash, is when you start to feel a major people management need 

Pedro on When to Hire an Executive

“Until you are at a point where it's repeatable enough. I think my mental model for executives in general is executives are really good at getting something that's working and expanding. They're not as good at 0 to 1. I have not met any execs that are good at zero to one. So I think like zero to one work is typically not the place where you want an exec to be. So I think if the sales process is still in that phase, I probably wouldn't hire someone.”

Vlad on His First Head of Sales

“In our case, it [hiring a Head of Sales] was after myself, one of my co-founders, and an internal person from customer success that we actually converted to our first AE. Once we were overwhelmed, once we knew what was selling, what was working, and we needed experience that we didn't have actually building a functional operating sales team. So we knew that if we were to hire that person, they would have something to sell in scale. And I wouldn't do it before that personally. Until you know the motion to sell…I've heard quite a few horror stories where people were gonna hire a sales leader and they're [the sales leader] are going to develop the go to market motion and bring that product to market. It almost never works.”

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Internal Promotion versus External Hire(s). No right answer.  

• Both Vlad and Pedro looked internally when they had leaders scaling well within the target function
• The reality is certain people won’t grow at the same rate as the company pushing you to look externally
• In these scenarios, hire externally or make an adjustment internally. Waiting too long to make a change has a large blast radius as the function won’t hit its targets, will add headcount, and directs will be less productive

Vlad on Balancing Internal Promotions with Company Needs

“We try to do that [scale internally]. We are usually only looking for a more skilled exec once we know something internally is sort of stretching or not really working. The other thing that I've just learned is that trying for too long to invest into folks on the team who don't quite have business scale experience that you are going to be at, let's say a year or two years from now. It actually doesn't just burn them, it's too much change for the people who report to them. You start to hear that they can see their leader being overwhelmed. A lot of times, as smart and capable as those people are, scale changes faster than people can gain that experience. And then you kind of have to think by giving them a shot for longer. Not only are you setting them up sometimes for failure, when you kind of have a sense that it might not work for much longer. You're also putting more change management, more manager changes on their directs, you're increasing retention risk for folks who are looking for a leader that they can learn from and that's far ahead of them. And there's just so many dynamics here where you want to invest into particular people, but at the end of the day, I've found that it is a net bigger positive to bring in folks who you know, have all the table stakes things like match on culture, they lead people in the way that the company expects in our cultural norms and the core behaviors sort of demand but it's just it's like a night and day difference when somebody comes in with years and years more experience. The entire team and even the people sometimes who are in that position who get leveled and now have a new boss that's coming in to take the job or promotion that they wanted. They go from this is absolutely not what I want to three months later saying holy crap, thank you for bringing X person in. I'm learning so much and my job is more enjoyable.”

• Internal promotions can scale, but they will require investment and mentorship to grow with the company
• In the early days, Brex didn’t have a way to develop people. As a result, 100% of the e-team was external
• Today, 3 of the core 7 leaders are internal hires only made possible because they were trained by prior leaders
• In some cases, Brex paired young leaders with external advisors via formal agreements to drive development

Pedro on When Internal Promotes Worked at Brex

“I think we didn't really have a way of developing people early on. So I would say probably until early last year was probably 100% external and now we have three people that are entering promotions into leadership roles. We don't call them c-level roles. My CTO, CFO, and my COO. I think the only reason it's possible is because we had leaders before that were really good training them to the point where they could go and take the stage.”

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Executive Hiring: Identifying Candidates

30%-50% of execs won’t work, but the ones that do will drive huge returns for your companies

• On average, 30%-50% of leadership hires won’t work - these mistakes will be costly
• Each change will require you to rebuild a function, shift the makeup of the team, and replace a leader
• So why hire executives? Much like in VC world, the ones that work payback your entire investment+more
• Therefore, it is in your best interest to get really good at this and to invest a disproportionate amount of time in hiring great executives. Both Vlad and Pedro spend 20-30 hours (or more) with the executives they hire.

Pedro on Executive Hiring

“I'm sorry to say but executive hiring is hit or miss. Every single founder I've met has said at best 50% work, maybe you're amazing and then 70% will work but you're still gonna get 30% that will not work and it will be incredibly costly, and a huge waste of time. And the reason why it's worth doing it is because the ones that work, kind of similar to VC land, pay off for the ones that don't work because they add so much value and impact. I think early on, our track record was much better and then it got a lot worse and then now I think it's getting better again.”

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The single biggest predictor of executive success: Ability to operate at all levels of detail.

• Conventional advice suggests that the best leaders are primarily great managers of people, not ICs
• The reality is the best leaders have a deep understanding of their function and the details of performance
• Red flag: If leaders 1) consistently defer for details and 2) push a narrative that they are a people manager
• The best leaders operate at all levels meaning they are exceptional ICs, understand their function deeply, and can also manage people

Pedro on Operating at all Levels

“I think the biggest misconception in hiring executives if I look at every single exec hire at Brex, and like what's the single biggest predictor of leadership success across the board, and of course your values matter, of course your goals matter, all that matters. But the single thing that became the biggest proxy for success for us, is the ability to operate at all levels.”

“We were running a CTO search and I was like, look, this person has to go through a technical interview. They have to know how to code. They have to understand systems. They have to understand what's going on. And the search firm said, when you get to CTO scale, they're not technical anymore. You're just people managers. And I was like, whoa, whoa, whoa. No. They have to be in the weeds. They have to know how to code. And I think the ironic thing that I found out is that the best leaders we've ever had, had a deep understanding of the technicalities, and the details of what made a function great.”

“I have allergic reactions when I hear things like “let me follow up with my team. Let me follow up with the person doing this”. No, No. You were doing it. Like you're responsible for this thing, not like your team.”

Vlad on Operating at all Levels

“huge plus one on expecting leaders to be in the details. I found that they shy away and use that excuse. [If they say] well, at this scale, it's more about people management. Huge red flag.”

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Build a criteria and archetype for what you want. Meet with the best people to inform your view.

• Knowing what you want is key to successful executive hiring, and this doesn’t mean writing a job description
• Both Pedro and Vlad spend time upfront coming up with an archetype for the role. In the case of Pedro, it's a simple one-liner that distills what they want into a single sentence. In the case of Vlad, it's 3-4 priorities that a candidate must have. This helps you sift through candidates objectively and focuses your interview process
• One tactic to do this is ask your network to meet the 3-5 best leaders in your target function. This helps you understand what is out there and also come up with an archetype that works for your company.

Pedro on Knowing what You Want (CPO Hire)

“It’s more useful to have an archetype that you're looking for. So what we did early on is we asked our investors to introduce us to the three to five best product leaders they’ve met and then I think it gives you a sense of what exists and that helps you to basically sort of set a clear one liner of what you want. For Chief Product Officer our sort of description was we wanted a GM, like someone that managed all the functions that by the way had a product background.”

Vlad on Knowing what you Want (CPO Hire)

“So even though we work on a job description, every search that I've done in the last two years at least, I just focused on three or four key priorities and as a way to align with both like the candidates but especially the search firm early on and how they present candidates.”

“A product CTO that knows how to code, understands web design and web development because our product is all about web design abstractions and web development abstraction, so you have to understand HTML, CSS, JavaScript, etc.”

Partner with a search firm to access a wider network of great executives.

• Search firms are a great way to extend your network for executive roles without significant time investment
• Vlad @ Webflow didn’t partner with search firms initially because he was hesitant about cost
• The one thing he would have changed in hindsight is to partner with firms earlier to augment his internal work 
• Note that quality varies considerably by partner at each search firm - ask us for feedback if you need it

Vlad on Search Firms

“One thing that I wish we had leaned into earlier was just working with search firms. I think for the first few searches, we tried to do it all ourselves and search firms. A) They have a ton more connections right despite having great investors and good networks, especially firms that focus on a specific function. There's just like no replacement in my experience to getting access to their networks, and having their guidance and sort of structured process to go through and actually run the search. Earlier on even when we were like 10, 15, 20 million ARR, I was really concerned about paying these firms like $100K-$200k for these retained searches. And I wish we had started working with the best of the best sooner, because once you have that experience, it's worth every penny. So I'll just say that upfront.”

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Executive Hiring: Running a Great Process

• The process will involve 1) initial conversations, 2) follow up discussions, 3) an interview loop with the team, 4) a case study working session, 5) references, and 6) dinners and meals for closing. Vlad and Pedro meet with 25-30 candidates per process and 20+ hours with the finalist candidate.

Best Practices: Initial Conversations

• Go deep with the candidates into their backgrounds. Instead of hypotheticals, understand exactly what they accomplished in their roles and to learn about their guiding principles. This is a great way to test for ability to operate at all levels and decision making alignment. The best candidates will be able to go to the L3 level of depth. Red flag if they can’t properly go into sufficient depth in prior roles.
• Another way to test for ability to operate at all levels is to ask candidates what they expect of leaders. If they mention things that suggest they expect intensity and detail orientation, they likely expect this of themselves. Vlad uses this tactic to tease out whether candidates will dive into the details early in his interview process.

Pedro on “Going Deep” in Initial Discussions

“The thing here is just understanding what's the role they played. I don't like tricky questions or hypothetical situations. I think our interview style is typically like, let's dive incredibly deep in your background. Tell me exactly what your day was like when you were at Meta in London in the London office, like, what did you do? You woke up and you got to the office at what time? Which meetings did you have? Which people did you manage? You know what outcomes you drove? Like what kind of customers you were talking to? I think that's really valuable. And I think people just don't go deep enough in backgrounds in general. And then, you know, this was sort of like an overall first meeting. And then we had a second screening where we're talking about structure and I gave him a product demo. I always do product demos in meetings. Then I talked to him about war time.”

Vlad on Testing for “Ability to Operate at All Levels” Early

“One thing I use to vet [ability to operate at all levels] pretty early is asking them what they expect of their leaders and how they think about that. If they have a similar expectation of their leader [it's a good sign]. The first thing [his CPO] said was I expect my product managers to have engineering backgrounds. And I expect them to be in the details. Sign number one that they also expect that in themselves. You can't give people a take home after your first conversation so you kind of have to tease out earlier by talking about how they expect their leaders to operate and sometimes asking them to share how they structured career frameworks in the expectations that they outline is a super helpful way to see how they operate.”

Best Practices: Interview Loop

• Design an interview loop where they meet all the relevant team members. Align with the team on areas each interviewer should test and tie those back to the archetype/principles you created during the initial identification phase. Best practice is to batch meetings. Typically 10-14 hours across a few days.

Best Practices: Case Studies

• Throughout the interview process, work through real problems with potential executives to see 1) if they are willing to go into the details and 2) their principles align with your company. In the case of Brex’s CMO hire, Pedro fixed website copy with the candidate and aligned on messaging. With his CPO, Pedro walked through their Middle Market positioning with the candidate and refined the pitch.
• Additionally, ask executives to work on a take home. Best practice is to have the case be a problem the company is facing now. Also include an “invitation to ask for more data” in the request - the best candidates will always ask for more information. Set up 60-90 minutes to discuss their takeaways.
• Include relevant decision makers in the follow up discussion. Best practice is to have this meeting be structured like an actual working meeting. This is a great way to see how the candidate interacts with the team, but it also gives the candidate a glimpse into how your team operates.

Vlad on Working Sessions During his CPO Hire

“We always choose something that the company is facing right now, the problem that they will have to solve once they're in seats. So in this case, we shared our company's strategy with all the finalist candidates. And we asked them a bunch of open-ended questions around how we are going from one product to multi-product. We leave it completely open-ended… Every single person who has been hired, takes it [the case] to the extreme. We say this shouldn't take more than a couple hours. But the ones that make it through are the ones that like once they get this prompt they will ping you with you know [questions]. There's an invitation here. Please reach out with any clarifying questions or requests for data. It's almost like a foregone conclusion that if somebody doesn't get in touch to ask for more information [they won’t be hired]. The best candidates always send a request of like 20 different things like latest board decks, latest customer breakdowns by segment, latest metrics, NPS reports. In this case, you know, our finalist asked for the voice of the customer, details on community, our practicing packaging details. Then they created a pre-read deck that she sent out to the rest of the working session team that walked through a ton of different frameworks and thoughts around how she would structure a multi-product expansion and that then is used in the working session. The encouragement for each executive is that they treat this time as if they were running this like they were solving this problem and they were already in the company. So it's not a one way presentation. It's a facilitated conversation where they get to see how our other peers and execs show up and our team gets to see exactly how deep they go into details etc.

Pedro on Testing for IC Skills

“We screen for very close to individual contributors skills at the exec level, which is very controversial and people hate it. When we were hiring our president, we were literally building a deck for how to pitch a customer and a product together and iterating on it and like going through it. You know, our CMO that we just hired, we rewrote my website copy with him to just literally see what the experience was like. So it was pretty intense. And then we had a challenging time with our CRO most recently. And when I look into why it was because we didn't do the same [test for ability to operate at all levels]. We didn't like you know, go into a sales call and say how do you pitch this? So that was like a big learning for us and something that we do in every single leadership hire like assess for IC skills and be really rigorous about it because they can't teach someone unless they know how to do it.”

Best Practices: References

• Do both front channel (candidate provided) and back channel (your network) references
• Share reference feedback with final candidates and go deep with them. This helps 1) understand feedback more accurately, 2) come up with a plan for development areas, and 3) tests for humility
• If candidates aren’t open to accepting feedback or do not acknowledge feedback, this is a red flag.

Pedro on References

“We did 15 references…We wanted to go really really really deep into like hey what exactly happened? Why are people telling me that you're political? I said [to the candidate] a lot of people (15 out of 16) said your political. How do you see it? He's like, look the reality is at any big company, you have to create allies to get anything done. And then you know, you go deeper and then you understand what happened. Otherwise I think you stay at surface level. We did a lot of it. Probably more than most people would, and we probably wouldn't do 15 or 16 if they were all glowing from the beginning. But x is a break glass kind of person and he doesn’t necessarily make everyone happy around him. But it's not a popularity contest, right? My co-founder pushed a lot on this, you know, let's make sure we understand what the good is and we could have disqualified him earlier, which would have been a huge mistake.”

Vlad on References

“I talk to at least 10 people. I'm mentally prepared that everything that comes up in this conversation I'm going to discuss with the candidate and you know it might not have all the details that might identify somebody but I'm always talking about things I heard. I mention it to every person I talk to. Whether back channel or front channel is my goal is to make this person successful to figure out whether what they say they've done in the past and how they show up is actually the reality in practice. Every one we hire will have the offer being contingent on us walking through all of the records of areas that are potentially gaps or patterns that keep coming up. I want to make sure that we talk about them as they are onboarded.”

The most dangerous hires are ones that fail slowly. Most founders wait too long to make a change.

• The most dangerous executives are the ones that fail slowly - their mistakes compound over years
• In the case of Webflow and Brex, they both had early executives they held onto for 2-3 years that they could have moved on from much earlier. In both cases, they coped with uneasy feelings coming from the decisions those executives made. 
• If you have a feeling something is not working out - trust your gut or at least explore that idea more. As the CEO and co-founder, you have more context than any externally hired executive.

Pedro on Executives that Fail Slowly

“I think that people that fail in six months are not the most dangerous ones. The most dangerous ones are the ones that slowly don't succeed. Because it just takes you away from the massive opportunity that is having an amazing player in the role. [The example he is thinking of] was here for two years. It probably took us a year longer and we just made, you know, not the best decision we could have made in the product experience over that time. And I think I got farther removed from the product, which was not something I enjoyed, but at the same time I wanted him to be successful. So I coped with it. And I think I was too apologetic”

Vlad on Executives that Fail Slowly

“I wish I had more conviction earlier that something can't be fixed. It's the opportunity cost. That's the killer. Totally agree. Like when somebody doesn't work out within the first six to 12 months, so much easier to recoup your opportunity loss than it is two to three years in. So. To the question of could we have vetted it in the interview process? Maybe if we had the same criteria that I just outlined for the [recent] search that you know somebody has to be technical etc. I didn't have that conviction before. I just didn't know what [I wanted]. I kind of was more thinking about, hey, these folks are like experts in their field or in their function in their practice. And you can just see over time, how lacking some of those things that are like more company specific needs, leads to longer term kind of divergence of whether they can be successful in the role or not.”

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Maintaining Your Company’s Identity

• As you scale, it’s easy to shift away from what made you successful initially. Executives with big company experience come in and they have expertise you don’t have. It becomes natural to defer to their plans or approaches because you want to 1) let them succeed and 2) they are the experts
• This happened to both Webflow and Brex. Both companies shifted away from a “builder” oriented culture to a culture centered around people management and process. Both companies reset their cultures in the last two years to orient around principles that initially made them successful.
• Per Pedro, it’s important to “not be too apologetic” and run the company the way you want to run it. At the end of the day, the decisions you made early on are the reason the company exists and is at scale today.

Example: Culture Reset at Brex

• Managers and executives were increasingly divorced from the work and overly focused on people managing
• Brex decided to reset its culture to reset how the company works and how the company builds its products
• To do this, Pedro made a change to the 1) team structure, 2) cultural principles, 3) working style with leaders, and 4) pay / wfh expectations

1. Team Structure

• Pedro promoted leaders who were closer to the details and eliminated the concept of “People Manager”
• He made this change because the people making the decisions were increasingly divorced from the work
• He also clarified that leaders are judged on the product/output and not on the size of their organization 
• Managers still have people management responsibilities, but only outcomes will drive career success

Pedro on Removing People Managers

“Two months ago, I decided to keep people that we're closer to the details of the job and not having a manager in between doing much. We eliminated the people manager role at Brex. Also, we did a lot of changes in culture, but there's this concept that this person has to be a people manager. We don't have those anymore because you can't manage people divorced from the work. You're managing the work, you know, and by the way, you have people involved. I spent a fair amount of time with Brian from Airbnb, who influenced a lot of my thinking on this. The analogy he gives is you can't imagine Johnny Ive at Apple managing the people and the design. No, he's managing the design and people is just the way you scale yourself right to get more leverage and more done, and sounds simple, but it's something that I think a lot of time gets lost.”

2. New Company Principles

Principle 1: People who work at Brex are high energy and have high conviction.

• Brex does not have room for “people who do not believe in the opportunity ahead of Brex”
• A lot of people were at Brex because it was a good company and they were good on “paper”

Principle 2: People at Brex are builders that can operate at all levels

• Brex clarified the archetype of who works at the company and reset expectations for everybody

Principle 3: Growth means increased responsibility of the work product, not a larger organization

• Brex clarified that success means more responsibility, not more people or larger organizations
• This might mean simple, but growth at large companies typically means more management oversight

3. How Pedro changed his style

• Pedro felt he became apologetic and deferred how the company was run to executives as they scaled
• For certain things you strongly believe in or hold core principles, it is ok to dictate approach to the company
• Pedro felt he let executives have too much control on parts of the business he felt strongly about
• With this change, Pedro reset the company to operate the way he felt would make it the most successful
• As an example, Pedro killed their old product team-led planning process. Now, planning is top-down oriented

Pedro on Changing his Style

“A lot of the time execs come in and say, oh, like, this is how it's supposed to be done. No, this is the way your company did it. We're here, we're gonna do it this other way. I'm not saying ignore all exec advice. I think what I'm saying is some things you know, don't be apologetic in what you believe. Because like, at the end of the day it is your company and we've had enough situations of an executive leaving and guess who's left off with the mess. It's you, right? And then the exec sometimes says, oh, you know, I want to make this change. I think we should run it differently. I want to change your expectations for roles. There is this balance between giving them autonomy but at the same time, it is your company. And I think over the past six, seven years, I think we probably gave more leeway than we probably should in terms of how we ran the company. And now we sort of took it all back. And, you know, product was an example. We killed our whole planning process. Now we just have one roadmap for the whole company. And we release four times a year, three themes for release. And I pick every single thing. PMs hate it, but you know, we have a lot of clarity and focus.”

4. Other Changes

• Brex reset employee equity and tied future growth in compensation to equity instead of cash
• Brex increased in-person time for the entire company

5. Outcome

• The change was very bimodal - either employees were energized by it or they left the company 

Pedro on Sticking to his Convictions

“I stopped being apologetic about how I wanted to run the company. It was: what is the environment that I feel like I can be the most successful in and sort of plays to my strengths. And I think my strengths are typically being close to the weeds in product and customers and I just sort of build a company around that….I wanted to [make the changes] because I thought the company would be more successful. And we did it but we had to break a lot of glass and I'm glad we did it after all.”

Pedro on Outcome

“It was very bimodal like either people loved it or they hated it, and a lot of people just left. So you know, it was a little bit unpopular, but I think we sort of got into a big company mentality too early, which was not great.”

Here is the post Pedro wrote on the changes they made at Brex in March 2024 and that he published publicly.

Example: Culture Reset at Webflow

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• The archetype of the team at Webflow shifted away from the technical builders close to the craft
• Increasingly, people at Webflow were people managers and not builders of product or outcomes
• To address this, Webflow introduced 1) new cultural principles around builders and 2) tied performance to these cultural principles. This made it clear who would be successful at Webflow and who would not
• Webflow also made it easy for people to leave by giving a financial cushion to anyone who didn’t see a future at Webflow. This was easier than having managers put people on PIPs to manage them out of the business

Vlad on Resetting Webflow

“We'll call it Webflow 2.0. A new set of cultural principles, and it was all around orienting around builders, like people close to the craft, not just you know, people management, and then we hired leaders, our CTO and our CPO oriented around that. And then each of them are baked into career guidelines. It just made it clear that this is how people are being gauged in promotion cycles and essentially how people are rewarded. People saw the writing on the wall, where they would not be able to become technical overnight. In our case, we didn't do a hard hard line RIF, but it was like a multi-month process where some people stayed, well many people stayed because they already had that archetype but quite a few people who were, on paper, amazing, in terms of their LinkedIn experience, etc….It was sort of mutually beneficial for us to part ways. We made it easy for them by saying, Hey, we're not going to put you through like a pip process and here's a financial cushion to make the decision easier”

Chief of Staff

A Chief of Staff is an amplification of you. It is a 2-3 year role and great training for future executives

• The Chief of Staff role is different at every company and depends on what the CEO and founding team want
• Typically, a Chief of Staff will stay in the role for 2-3 years before moving onto a new role within the company
• The ideal Chief of Staff is someone you trust to make decisions as they are an extension of you and your style
• The Chief of Staff role is also a great “training ground” for exes. Pedro’s first Chief of Staff is now Brex’s CFO 

Vlad on Chief of Staff

“I hired a Chief of Staff in late 2020. We were probably north of 75 million ARR. At that point, the company was 300 Plus. My Chief of Staff is more like a Chief of Staff to the entire exec team. So it's not a scheduling role. It's very much like a VP light type of thing where she tries to make sure that the entire exec team is operating really well. She is a reflection of me and an extension of me, but it is not an EA plus type of role. It's a lot more strategic…I felt it was necessary when it felt like a lot of things were falling apart on the exec team. Mostly because of operations and like not enough time spent together, right? So it's a way just kind of like the glue of knowledge between the exec team and the rest of the company.”

Pedro on Chief of Staff

“My mental model is yes, my Chief of Staff helps run the exec team. No question. I typically [hired] someone from inside the company that we would promote into the role and then later on, I try to put them in a bigger role after. The reason is [this is] someone that will help run the team, but at the same time, just learn a lot about how I think and how the business runs. So the history of Chief of Staff: My first one, my SVP of operations was really strong and joined Brex super early. And I was like, hey, like, I know you don't want to do this but come be my Chief of Staff. And then we hired another leader for operations. He came to be my Chief of Staff. And he did it for three years. He was amazing. My principle for Chief of Staff was like, if a bus hit me, would I trust their decisions in terms of how to run the company and the exec team. It doesn't mean they're like a CEO replacement, it just means that on the small day to day decisions that you have to make, like, do I trust him and I really did with X and then he later on became our CFO, which was, an unorthodox path for a Chief of Staff.”

Scaling Recruiting

In hyper growth, create systems to scale the the founding teams hiring bar to maintain team quality

• If you plan to 2x headcount, it means that 50% of your company will have <12m tenure by the end of the year
• It’s almost impossible to maintain hiring quality without systems to scale the quality bar of the founding team
• Brex faced this challenge when they 7x’ed the team in one year - going from 50 to 350 people in 12 months
• To scale quality hiring, Pedro realized it would be impossible to train every manager given the pace of hiring
• Instead he decided to manage recruiting directly and hold the bar through his recruiting team of 5-6 people
• This let Pedro scale his hiring bar through a small team of recruiters versus 10s of managers at Brex

Pedro on Managing Recruiting to Scale Hiring

“We went from like, maybe 20 to 50-60, then from 50-60 to 350. And what I learned during that moment is–and we had to do it–because we were growing. I mean we went from 10 to 100 million ARR in 11 months, so you just literally couldn't keep up and we just had to hire. And I wouldn't have done it that quickly if it was up to me, but we had to. And one of the things we learned was your hiring managers are new, and they can't hold the bar. Not because they're bad, just because they don't know the bar. And what we did instead is I spent a lot of time really close to recruiters. And because there were like five or six recruiters, it was easier to hold the bar through them versus to hold the bar through every single hiring manager. And recruiters had a lot of power to say no…recruiting  really, really helped hold the bar high.”

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II. Case Studies

Webflow’s CPO

Archetype
Vlad picks 3 or 4 key priorities to guide candidate identification and focus areas. For CPO, they wanted someone with:

1. Technical background with deep domain expertise in web design and development
2. Track record of leading, hiring, and retaining teams that skew technical and craft oriented
3. Significant experience (or leading as a GM) in commercial growth teams of at least $300M ARR scale
4. Experience with expanding from a single to multi-product company; M&A track record is a big plus 

Initial Meetings
Vlad met with 25-30 candidates in the process. Vlad had 1 or 2 initial meetings before passing candidates to meet the broader team and to invest in a working session. During these initial meetings, Vlad goes deep into their background and tries to align on whether they fit the 3 or 4 key priorities that they outlined. This amounted to the following for Vlad:

• 1 hour with all 25 to 30 candidates to calibrate and see who he wanted go deeper with
• +2-3 hours with 5 to 10 candidates to go deeper on the 3-4 key priorities with Vlad

Interview Loop & Take-Home
For finalist candidates, they set up a series of onsite interviews to test for the criteria that Vlad outlined. Each of the interviewers posted their questions in a shared Google Doc and uploaded feedback directly to Greenhouse so that Vlad could review it. Vlad chose to do this instead of a group discussion, so he could get unbiased feedback.

Onsite #1

• 45 minute Meeting with Vlad on product strategy
• 45 minute Meeting with COO on operational excellence
• 45 minute Meeting with CTO on engineering excellence

Onsite #2

• 45 minute Meeting with CMO on customer and community
• 45 minute Meeting with Director of Product on coaching and development
• 45 minute Meeting with Director of Sales on enterprise sales
• 45 minute Meeting with People leader on leadership and DEI
• 45 minute Meeting with Chief of Staff on alignment and partnership

Onsite #3

• 45 minute Meeting with Vlad on core principles and relationship building
• 45 minute Meeting with co-founder on new product philosophy
• 45 minute Meeting with Head of Product Design on product design
• 45 minute Meeting with co-founder on design philosophy

Take home / Working Session
Vlad provided an open-ended prompt on expansion from single product to multi-product company. They asked the candidate to prepare their feedback on this topic and to present during a 60 minute working session with the relevant team. Candidates are encouraged to ask for more information. Internal team members are encouraged to treat it like a normal working meeting. The best candidates go above and beyond and prepare detailed presentations or memos on the topic to lead the discussion.

Final Onsite #4

• 60 minute Meeting with Product leadership as a debrief/continued discussion from working session
• 30 minute Meeting with Board Member #1 as close meeting
• 30 minute Meeting with Board Member #2 as a close meeting

References
Vlad spoke with ~10 people. During these interviews, his goal is to understand whether what the candidate says is reflected in their actual work. After collecting all feedback, Vlad makes the offer contingent on going through the feedback and identifying areas for development together. Below is his rough interview script.

• Background on working relationship
• [Manager and Peers] What advice would you give me to make this person successful?
• [All] In what areas and skills have you seen [X] grow most significantly when you worked together?

[All] In your experience, what top words would people use to describe [X’s] management and leadership?

• Dig into words they use to understand details behind each term
• [All] Do you have any examples of when you disagreed on something? How was it handled?
• [Directs] What was it about X that made them a great manager? What is one thing they were better at than anyone else?
• [Technical] Can you think of any examples where [X] demonstrated deep technical or domain expertise?

Brex’s CPO 

Archetype
Pedro distills needs into a simple one liner after meeting with great Product leaders at other companies. For their CPO, Pedro identified the following archetype: An executive that has GM experience (e.g., experience running a P&L and all the functions of a team) and also has product experience.

Initial Meetings
Pedro met with 25-30 candidates in the process. Pedro had 1 or 2 initial meetings before passing candidates to meet the broader team and to invest in a working session. During these initial meetings, Pedro goes deep into their past experiences and rarely focuses on hypotheticals. He finds that this is the best way to screen for “the ability to operate at all levels of detail” early in the process. Questions he asked during these meetings:

Background

• Go deep into personal background - where they grew up, why they made decisions, college/school
• What are your product philosophies and principles?
• Why would your X teams not have achieved outcomes without you?
• Go deep into work background - what they accomplished at each role? What did THEY do? Why?

Working Together

• How would we work together? How would our 1-1s, team meetings, product review be?
• How would you feel about me going deep into the product? Engaging with PMs?
• What is your style in running a product? Do you go deep or let teams run with their goals?
• Where are we going to clash? Simulate a disagreement and see how it goes.
• What are your product primitives?
• What do you need help with? What are your weak spots?

Operating at all levels

• Pedro walked through their Enterprise deck and they brainstormed feedback/messaging

Interview Loop & Take-Home
For finalist candidates, they set up a series of onsite interviews and working sessions.

Interview Onsite

• 60 minute Meeting with CFO
• 45 minute Meeting with Head of Sales
• 45 minute Meeting with former CPO
• 30 minute Meeting with Chief Legal Officer
• 30 minute Meeting with PM of Middle Market
• 30 minute Meeting with PM of Banking
• 30 minute meeting with PM of Platform
• 30 minute meeting with PM of Growth
• 30 minute meeting with PM of Design
• 30 minute meeting with board member #1
• 30 minute meeting with board member #2

Take home / Working Session
60 minute working session to discuss positioning of Middle Market and Website. They worked through the deck live and iterated to make improvements on it. Pedro, co-founders, Head of Engineering, Head of Sales, PM of Middle Market, and Chief Marketing Officer were all in the meeting.

References
‍Pedro spoke with ~15 people. After speaking with references, Pedro walked through the feedback with the candidate to deeply understand reasons for each consistent point. Sharing feedback back with candidates is critical as it helps test for humility and self awareness

The information presented here was produced in March 2024 for avra batch #2.