Executive hiring is incredibly difficult to get right — Robinhood COO Gretchen Howard shares her playbook

Gretchen Howard: I call this like a knower attitude. They come in and they're like, oh yeah, I know how to solve that problem. Let me tell you how you would do this. Versus the candidates we ended up hiring had much more of a learning approach. So their answers to the same question would be. Oh, wow. That's an interesting and complex problem.

Here are some of the questions I would ask to try to get more information, to get to a better outcome. So immediately in the answers, you could see their style come through. The first one is what I call a knower and the second was a learner. And I think, again, that is a sign of humility, but it's also a sign of.

First principles thinking like, are they open to changing their perspective? Are they intellectually curious? That's what's going to make them successful.

Brett Berson: Welcome to in depth, a new show that surfaces tactical advice, bounders and startup leaders need to grow their teams, their companies, and themselves. I'm Brett Berson, a partner at at First Round, and we're a venture capital firm that helps startups like Notion, Roblox, Uber, and Square tackle company building firsts through over 400 interviews on the review.

We've shared standout company building. The kind that comes from those willing to skip the talking points and go deeper into not just what to do, but how to do it with our new podcast. In-depth you can listen into these deeper conversations every single week. Learn more and subscribe today at firstround.com

On today's episode of in-depth. I'm thrilled to be joined by Gretchen Howard. Gretchen joined Robinhood in early 2019 as the company's COO and just its second executive hire. She climbed aboard the Robinhood rocket ship after five years building at Capital G, Alphabet's investment fund. When she joined Robinhood as its COO, one of the most critical tasks on Gretchen's to do list was building out the company's executive team to support the co-founders of Vlad and Baiju.

So in today's conversation, we dive really deep into what she's learned about executive hiring. To start, she explains how to align the hiring profile to the trajectory of the business to make sure you're investing in the right places. She also unpacks her hiring philosophy as it pertains to Robinhood, including balancing financial industry expertise, with an innovative hands-on mindset that's critical for rapidly scaling startup.

Next, she walks us through the executive interview process she's crafted at Robinhood, including the three traits that are always at the top of her wishlist for candidates, including sussing out whether someone has a knower versus learner attitude. She also explains her complicated feeling towards certain interview exercises and how she leverages referenced.

Finally, she shares her tips for successfully onboarding new executives. So these hires don't result in what she calls organ rejection, along the way, Gretchen shares tons of real life, examples of how she's applied these principles in her role at Robinhood. If you're struggling with your executive hiring, whether it's coming up with the right candidate profile, aligning on culture fit, or finding that your interview process just doesn't seem to be surfacing the best candidates, this conversation really is a must listen. I really hope you enjoy this episode. And now my conversation with Gretchen. Well, I'm super excited to get to do this with you, Gretchen. Thanks for joining. 

Gretchen Howard: Thanks for having me and this'll be fun. 

Brett Berson: I thought it would be fun to start our conversation around building an exec team.

And I think it's something that we've noticed in working with hundreds and hundreds of companies that have. The trickiest thing to do once you have some level of product market fit and you begin scaling as a company, there's all sorts of trials and tribulations and challenges to getting it right. And so I thought maybe you could kind of set the context for the last few years of executive team building after you joined Robinhood and maybe just sonnet kind of talk about the state of the executive team when you joined and kind of how that evolved in those few.

Gretchen Howard: So to just go back in time, I started at Robinhood January 1st, 2019. So a little under three years ago at the time when I joined the two co-founders who were co-CEOs and they had hired their first executive Jason Warnick. Who's our amazing CFO. And he had started about two weeks before I did.

Jason. And I were really the first two outside executives. They had brought onto the team. And at that point we knew Robinhood had a great offering for customers with strong product market fit. And they knew at that time they had invent. In leadership to scale to that next level, we didn't even know exactly what that roadmap was going to be, but we knew that we had something special and we openly had a dialogue of how do we take it to the next stage of growth and who did we need around the table with what skillsets to be able to do that.

So I would say it was. An amazing time to join because Jason and I really got to spend some quality time with Vlad and Baiju and the four of us had a very open relationship in terms of communication and trust building. And when you're growing that rapidly, I think having. Time for leaders to really bond and know each other and really respect the differences and the different skills that we each brought to the table was incredibly important.

So I think some of the early conversations we had at that point was that there are different people who are right for different stages of our business. Some people can Excel in the early stage of a business. They may be great ideators, really creative, maybe. Wearing many different hats. And some of those people will like that next stage of growth where you have to specialize focus and scale, but others may not.

And that's okay. And so part of our job as leaders was to figure out how we could make that transformation effectively. So. I figure out the superpowers of each individual that you have figure out who do you promote from within to step up and take that next level role. And where do you have to bring in outside leaders to supplement the great talent you already have?

So I would say over the last few years, in my role as COO, I've spent a lot of time thinking about how do we help the founders build a really strong and diverse leadership team and. Really stepping back and thinking about what areas do we have to invest in when, because you don't have to do this all at once.

And it's not just about bringing in people with the right skills. It's about bringing in people who can collaborate and trust each other and think about what's best for the company and not just their own function. 

Brett Berson: I think that's great framing. So to break that apart into some sort of specific topics, what is the actual process look like?

To go from that norming stage of you joining. And in this case, Jason starting a couple of weeks before you, and then two co-founders who, so it's the four of you, like then what happens to figure out where to start in terms of executive hiring, getting alignment like that? Negative one to zero, we're ready to hire a chief product officer.

We are ready to hire X or Y what's actually going on. 

Gretchen Howard: Yeah, it's a great question. I don't think there's any secret formula to how to do it. I think what we did was align a lot of the thinking of where we had to invest in leadership to our big rocks or what we were trying to accomplish for, for our business at the time.

So Robinhood is a single app where we want customers to invest and save and spend all in one place. And so when I joined, they had really were focusing on scaling the brokerage business and the crypto business. And they had also just recently. Launched a self clearing platform. So one of the first things that I was asked to do was this self clearing platform.

No, one's built this in new technology in the last 30 years. This could be a huge differentiation for us and enable us to launch a lot of new products in the feature. So who is our leader to take the self clearing platform to the next level? So for me, I have. A very clear focus from day one. And the first hire actually made was our president and COO of Robinhood securities, which is our self clearing arm house.

And we talked a lot about as a leadership team. What attributes, what capabilities did we want in that person? And when we selected Jim, it was. He had more than 20 years of experience and self clearing. He had lots of different relationships across many brokerage houses. He had seen different cycles in the market.

He had the maturity to lead us into that next phase of growth. And so it was not only was he the best functional expert, but he also had the right cultural attitude. He knew. We could use technology to automate things that he had been struggling with for years as an operator. And he really also connected with our values.

He believed that it was a worthy mission to reach out to a new generation of more diverse customers. He believed in the mission of democratizing finance for all. And I think if he had just had. The functional expertise, but hadn't had the passion about rethinking operations, rethinking the whole self clearing model being okay to be bold.

He wouldn't have been the right fit for us. So for me, it was interesting journey because not only. Did I quickly have to be an expert in self clearing to select the best functional leader, but I also had to learn the Robinhood culture very quickly to make sure that this key hire wouldn't result in organ rejection.

It had to be someone who was innovative and collaborative and open to change and understood the power of technology. So it was helpful to me to have those discussions with Jason and flat and BU, and we had a lot of debate and they were all very involved in the process and how to say and who my first hire was.

That was incredibly helpful. 

Brett Berson: And so the discussion was, Hey, we all know that this is a really important bet. We need to hire somebody to own this. And then the discussion was what are we looking for in that person? Or what is the process to get. Alignment, because I think a lot of things go wrong when a CEO is thinking, I'm looking for X and another, co-founder's thinking I'm looking for Y and you end up in these like infinite searches that never closed.

Gretchen Howard: Yes. I think the first step was saying, okay, what are the four of us really good at? How are we different as a team? What do we bring to the table? And then what are those gaps that we don't have that we need to round out our experiences? So I think that first step of acknowledging where we can fill in the gap and then.

Identify the areas that we had to supplement with new hires was incredibly important. That was the first step. I think the next step was, of course we always hire for in this case, we wanted someone with deep financial services experience because. At the time we had hired a lot of great technologists, but we were probably underweighted on the deep financial services expertise.

I sort of bridged the gap in that I had worked at Google for a long time. I had worked at Fidelity Investments, but a lot of our folks were a lot of engineers were mostly on the technical side. So we needed someone with deep operational and deep regulatory skill that had been in that clearing environment.

So. The skillset, the functional expertise was the no-brainer I would say on the hiring, I would say the more difficult piece. And I think this is where a lot of leaders are. It's easier to make a mistake in this area. Is that for us? There were some non-negotiable. In hiring a leader that centered more around our cultural values.

So for me, the three attributes I looked for were really someone that had high humility, someone that had high authenticity, can they be themselves? Will they not be afraid to raise tough questions? Will they feel comfortable? Driving quality and velocity, and then trust, how will they build relationships across functions with product and engineering and how will they tackle innovation?

Are they open to change? Are they embracing change? So those three things, humility, authenticity, and trust for me. Softer attributes that I spend a lot of time on when I interview candidates because our recruiting team does a great job of finding best in class in terms of industry or functional expertise.

Of course, I interview for that, but I think what makes or breaks a leader being successful at Robinhood is some of those other skills because we operate differently than. Traditional financial services companies, and we operate differently than traditional technology companies. We truly are a FinTech company.

And I think that this mix of two very different industries and industry norms and bringing them together there are, we found that special sauce that works for. 

Brett Berson: When you think about those three cultural things that you spend a lot of time looking for, at least in this case with Jim, and then I assume it cascaded as you continue to build the exact team.

Are those things different than when you are hiring leaders at other companies in your career, or they're a consistent set of things you're always looking for, regardless of where you are. 

Gretchen Howard: It's an interesting question. I think at at least different points of my career and my own maturity, I probably early in my career.

Focused more on expertise. Will they be able to do the job? Will they actually be able to produce high quality work? Do they have the potential to grow and learn? I think over time as I've matured and seen patterns of what works in strong leaders and also evolve my own leadership style, I think I've probably weighted humility.

And trust a lot more. So maybe my gray hair is a, you know, a little wisdom has come with that gray hair over time. I don't know. But I think also at Robinhood, we do have a very unique culture that probably requires these attributes more so than other companies. And I say that because sometimes I talk about Robinhood culture as an anthropological exercise, we are bringing in people who have 20, 30 years at financial services.

Companies, which are traditionally on the more conservative side, very hierarchical and not necessarily transparent, very thoughtful in how they evolve. And then we have. A lot of engineers and product managers from technology companies, the Googles, the Amazons of the world. And it's all about iterating, experimenting, testing, moving quickly, being entirely transparent.

Well at Robinhood, we're now creating a world where these two we're hiring from both of those worlds and we're bringing them together and creating our own culture. So how do we create an environment where leaders can thrive. Employees can thrive where there's really respect around the table, where you may come with really different norms and expectations, but you're all at Robinhood because you believe in the mission, you believe are doing something truly valuable for customers.

And how do you learn to adapt your own style and actively listen, actively allow the best idea to come from anywhere. I think that comes with. Really centering on humility, authenticity, and trust. And so I would say that at least in art culture, I think these are probably more required than in other situations I've been in the past.

Brett Berson: And so for these three areas that you tend to focus, what are you doing in an interview to get to conviction on these different areas? 

Gretchen Howard: I'll use the example of our chief product officer. So we recently hired this amazing woman Aparna who brings all of these skills, but she's got an amazing track record and design and product development.

I think we spent a long time talking to a lot of great product leaders, but I think one of the things that when I interview people, it's multiple conversations, especially for a leadership position at this level. And. A lot of it is about how do they think, how do they like to collaborate? How do they go to first principles?

Are they asking questions? Are they intellectually curious? And so for me, it's more of an ongoing conversation than a set of interview questions. I like to understand how people like to interact, how to build teams. And I also tend to spend the first period of time in a leadership interview, really spending time understanding.

What would make a new role, a new experience, interesting to that person, what do they want to learn? What do they want to get out of it? Because especially for leaders, I think for all jobs, but especially for leadership jobs, it's almost like matchmaking. It has to be a match on both sides. The candidate has to.

No, they're coming to Robinhood because they're going to have a lot of impact. They're going to learn something new. They're going to be part of a mission they really care about. And from our side, they have to also be bringing a set of skills, expertise, characteristics that will complement our journey and help us achieve the goals we want for our customers.

So it can't be a one-sided conversation. So I tend to. Structure my first conversations with people with really trying to listen and identify what they are seeking in that next role. And I feel that helps us get to an understanding a lot sooner. 

Brett Berson: And so do you just ask, like what would be important in a new role or you poking at that or getting at that in a specific way or sort of an approach to those set of.

Gretchen Howard: I usually start with saying, I've looked at your background, incredibly impressive. I want to learn more about that, but first give me a little color. Tell me about what's important to you. Why do you do this role? You're in, why are you in this function? What motivates you and what are your. Hopes for this next role?

Like what do you personally want to get out of it? And it's amazing people really open up. I think they're surprised when I asked that in the beginning, but it actually then enables them to be much more open and direct in the conversations and the questions that I asked to come. And when I get to that point, I really try to focus around a few, again, a few of our company values.

So. One of our principles is radical customer focus. So I try to ask questions to see if they frame issues solutions through the eyes of a customer. Right. I think there's a big difference between someone who thinks about solving customers for the good of a company versus the benefit of a customer. The other value that is really important to me.

Participation is power. That's something. We talk about a lot at Robinhood and a lot of companies have missions. I think our mission of democratizing finance for all is not for the faint of heart. We've been in the news a lot. You have to really have a personal connection. Be tied to that mission care about the outcome or.

It might not be the right place for you. And so I try to ask questions around the tie, back to our values, and it gives a sense of, they talk about their competence in that area, but it also gives a sense of color and what's important to them. And again, we want them to land well at Robinhood. We want them to be successful and without those ties to what we really believe in, I think it's hard for hard for people to be successful.

Brett Berson: I don't know if this is possible, but if you think back to, you know, call it the last X number of interviews that you've done, can you give a couple examples of what the conversation looked like? And the reason that I'm asking is that a lot of people talk about hiring for values, but I don't think they're particularly good at.

Starting with, well, okay. We're very clear on the five things we care about and translating that into an interview process, such that they can leave with some level of conviction that this person spikes in those areas. I'm hearing you say that you're not saying something we really care about is humility and you're not asking them.

Well, tell me a story about when your humility was exemplified. You're asking a whole range of questions. And you're reading into the classic example would be if teamwork is something that's important to you, you might ask questions. And the more somebody says, I versus we might be a leading indicator that they might not be a teammate, but I'm curious if you can kind of bring it to life with some of the values, or maybe if you close your eyes and think of an interview, and somebody said something that gave you a lot of conviction that they would exemplify or be valuable.

Gretchen Howard: Sure. I'll give you an example of one of the things that over the last couple of years I've been hiring for us, we have chief compliance officers and all of our different business units. So the brokerage clearing firm crypto business, and there are. So many qualified, excellent compliance officers out there.

I would say in my interview process with some of them, there were some candidates who felt the need to prove to me how much. In some cases, explain things in a condescending way, but it was all about, let me show you how much I know. And I call this like a knower attitude. They come in and they're like, oh yeah, I know how to solve that problem.

Let me tell you how you would do this versus. The candidates we ended up hiring had much more of a learning approach. So their answers to the same question would be like, oh wow, that's an interesting and complex problem. Here are some of the questions I would ask to try to get more information, to get to a better outcome.

So immediately in the answer. You could see their style come through. The first was what I call a knower and the second was a learner. And I think that is a sign of humility, but it's also a sign of first principles thinking like, how do they interact with our colleagues? Are they open to changing their perspective?

Are they intellectually curious? That's what's going to make them successful. I assume the people that I'm interviewing have been vetted are highly intelligent, have amazing track records. So a lot of it is about how are they going to think outside of the experience they've already have and how will they evolve their thinking going forward that creative curiosity, I think when you ask the right questions and you can see the difference in people's answers quite rapid.

Brett Berson: Do you think that that sort of area, that Gretchen you were just kind of zeroing in one of the areas that increases the likelihood that you don't have the classic big company executive that doesn't translate to a startup environment or are there other parts to that problem and looking across lots and lots of companies, I've noticed that there are.

A lot of times when folks hire for experience, I'm hiring a sales leader and I'm hiring somebody from Google, who's managing a 900 person go to market team, and then there's often organ rejection. And I'm curious, is it that what you might consider as a know it all versus learning? Like, I'm going to take my playbook and just slam it down.

This company's throat. And obviously like the world is complicated. Companies are complicated and unique and so copy paste generally doesn't work. Or I'm really curious if you have any other thoughts because you have such an interesting set of hires that you made. Some of which maybe have been in financial services for 30 years, some of which may be, have even been in tech for 20 years or something like that.

And I think that is fraught with all sorts of organ rejection. And some of it may be pacing. Like they're just not used to what it means to be at a few hundred person company versus 50,000 person company. Some of it is to your point may be values aligned, but I'm curious any other thoughts on like what tends to go wrong?

When founders start to go and hire very quote, senior or experienced. 

Gretchen Howard: I've seen it happen all the time. And it's hard to know before you bring the person in house. It really is. I think we try to talk very openly about the concept of organ rejection and what works and what our expectations are before someone comes in the door and that has seemed to work for us.

It hasn't always worked, but we've gotten pretty good results from it. I think at Robinhood, we have an expectation that for leaders that you can. Step out to a thousand feet, do that strategic thinking. Be very visual. But there are times, many, many times that you have to roll up your sleeves and get into the details.

And that is just the norm here. When you're building a company, you have to act like an owner and you have to do things that maybe you spent more time 20 years ago doing, but you have to get in there and it's all about solving for the customer need. So I'll give you an example. We have. A huge spike in customer support tickets early in the year.

And we created this program very quickly in a day and called, put me in coach. And we had all levels of the company, regardless of the role jumping in and helping customers. And that's. Spirit of no one is too good. No one is above rolling up their sleeves and getting involved. And I think some leaders just haven't been in that position for a long time.

So I do think it goes back to attitude. I will say that we also talk openly about hiring people from many different sources. So we want to create the Robinhood way. We're not going to duplicate from financial services. TV or fidelity or on the tech side, Google or Amazon, we're going to take elements of greatness from all different parts and then figure out what is the Robinhood way.

And one mistake I made when I first joined is I started a week. A weekly interaction for managers and we called it leadership lab and it was all about, we didn't have a formal manager training program. So I said, all right, great. I've got all this experience. I'm going to come in and I'm going to teach all these people how to be great leaders.

And the first meeting, someone pulled me aside and said, this is great. We've never had this forum. I'm so excited, but like, we've got to figure out not how you did it before. But what is right for Robinhood in this moment, it turned into a dialogue. It wasn't me. Sharing knowledge, it was having a conversation about what would be most helpful and most effective.

And so I do think it's, it's very much that mindset of yes. Bring in your prior experience, bring in your knowledge. That is incredibly valuable, but come in with an open mindset that that's one in. To the new way of doing things. And I think when people don't talk about that openly upfront, when they bring a new leaders, it can be a shock because it will be very different from the norms that they've experienced before.

So I think a lot of transparency and previewing that what we expect of leaders is variable. 

Brett Berson: So zooming out a little bit, we kind of went down this cool rabbit hole. I was hoping we can kind of shift the conversation slightly and maybe zoom back out and talk about how you think about running a really good executive recruiting process.

And so maybe we could talk about it with a hire you made last year or a fictitious hire that you might make, and maybe you could walk us through how does it all work who's involved in? What have you learned about making that process? Both efficient and effective in increasing the odds that you bring somebody spectacular on this.

Gretchen Howard: Yeah, I think we are scaling incredibly fast and we're also fighting for top talent out there. It's one of the most competitive talent markets I've ever seen. So one of the things I like to focus on is how do we have quality interactions within every step of our hiring process? I think that. Open communication dialogue, ensuring that even if they don't end up joining us, that they have this sort of delightful experience interacting with us.

So I can walk you through how we do it at Robinhood. When we hire top leaders or executives, we partner very closely with our recruiting team or recruiting team spends a lot of time calibrating. Getting the business acumen on the profile that we want. So we may do a deep dive session with them, really understanding the functional skillsets and then the attributes that we are over-indexing on.

And they do a huge sourcing project and they come back to. With lists of people, different profiles. And we go through a process and we say, yes, this one is exactly spot on. Or no, this one is a little off because it doesn't have this type of experience or no, this one's jumped around a lot. Let's deprioritize that person.

So we spend a lot of time in that calibration stage. And I think that even though upfront, that takes some time, I think. Allows us to go much faster through the process after that. So the next phase is if it is an executive, we usually have one of our executives. It could be flat, it could be me, it could be anyone on the leadership team who is ever the hiring manager reach out to that candidate.

And I think that's important. Sometimes we have recruiters reach out, directly 

Brett Berson: run most of your exact searches internally. Or do you mostly work with the retained search? 

Gretchen Howard: We do a combination. So I would say we have a fantastic in-house executive recruiting team, but for some specialty hires we use outside recruiting services.

So I have a list of recruiters that I've worked with in the past. Some which I got to know when I was at Google capital or capital G and. I tend to like to work with very small shops that have specialties. So sometimes I use them. So again, I'll go back to sort of the compliance experience. I was hiring two compliance officers about a year ago.

One of them I had actually worked. 20 years ago, the other one was a referral from an employee. So we didn't need to use an outside firm that said when we are hiring for some other compliance roles, we didn't have necessarily have some of the industry connections. We valued that outside perspective. And so we actually used an outside firm to help us with that search.

So there's not a strict rule book about when we do it in-house or would we use an outside recruiter.

Brett Berson: Got it. You were saying calibration exercise, do some sourcing from your exact recruiting.

Gretchen Howard: So you could say we could also do the calibration and sourcing with an outside firm. So the same process would, would work throughout.

And then we set up what we call loop. So we have four or five people on the loop. We always make it cross-functional. If we are hiring someone in finance, there would always be someone from another function who would work cross-functionally with this role. And we think that's very important in terms of our hiring, partly because we want to make sure that we are.

Creating an inclusive environment and we're trying to eliminate bias whenever we can. So we run these loops with a highly cross-functional team, and we usually start off with a screening process done by the recruiter and usually the hiring manager. And we try to get candidates through the loop very quickly.

We have different areas that we have each person focus on, and we try to get back to the candidates very quickly, close the loop and calibrate. We try to do batch. So we can calibrate across different candidates and really understand and discuss why certain candidates are resonating and why others are not.

So sometimes for executive searches, this can go over a period of months for other levels, we can move as fast as a couple of weeks, but we really try to make sure that we are casting a wide net and having a very diverse candidate set to talk to for every leadership. 

Brett Berson: How do you think about the balance of buying and selling throughout the recruiting process?

Gretchen Howard: Yeah. I think the mistake that I've seen, that's very common as interview teams come in and they just go right into the buy. Right? Why are you good enough for us? Why do you want to work here? Show us what skills you have and. Sometimes the candidates don't have enough context as to the color on the role, how this fits into the organization, what the future path for this role is.

So I'm a believer that, that hiring manager really needs to take that time upfront to set the scene, put color to the role. Explain how it fits into the larger organization, explain the career path within it. And that will just make the candidate have more context to go into those other interviews. And it will be more fruitful conversation.

So I think early on in my career, I've definitely seen candidates that I've met at the end of the process. And they'll say, and I come in to sell at the end and then. Can we just step back. I don't even really understand the context of this role and I think that's a mistake. So I think there's still more work for us to do in this area.

I think we have to correct for that. Make sure candidates understand who we are, what our culture is, what this function is all about. What are the core responsibilities? How does the team operate? So doing that selling upfront and then going into the buy in procedure, it is a common mistake that. 

Brett Berson: When you talk about dividing up evaluation criteria across the folks on the interview loop, can you give an example of what that looks like at Robinhood?

And do you also, one of the tricky things I found about the divide and conquer way of recruiting is it becomes trickier for you as the individual on the loop to be convicted coming out of the time you spend together. If you only focus on like a very narrow slice. And I'm curious if you balance that in some way, or maybe ultimately it's the hiring manager, that's making the overall call and you just need Jane who's on the loop to tell you, is this person customer obsessed?

And as long as they can give you the answer yes or no there, then that's their role on the loop?

Gretchen Howard: I agree. There's trade-offs with being too focused and not having that holistic picture. So I think one of the things we try to do, especially for major hires or big roles is we meet as a group beforehand. We talk about how we're going to divide and conquer, and they could be anything from coaching development, skill, leadership, skill, building, large teams to working cross-functionally.

So if there's someone that has to work very closely with engineering and they're not in the. The function we'll have an engineer come on and say, would you like to work with this person? How are their communication skills? So we break it up into a series of different attributes that again, go back a lot to our values.

But I do think it's important to at the beginning, at the outset, really hear from the hiring manager, what is critical for this role? What are they looking for? What will success look like? Because that gives the interviewers broader context as to what they should focus on. So. Even though one person might be focused on the people management skills.

If they're in the crypto space, they can still weave in questions around crypto, around that functional expertise to get a more holistic stance. So we're not so strict that you can only ask these questions. It's a very fluid conversation, but we do. We divide and conquer so that the candidate doesn't get the same questions and we approach it from many different angles and triangulate.

And I would say it's not just the managers called the end of the day. If the manager is supportive of the hire, but the rest of the loop is not supportive. We don't go forward with that candidate. We take all of the people on the loops input really seriously because we want this person to succeed at Robinhood.

And that's just not a good indicator if they haven't gotten the support from the. 

Brett Berson: So in terms of the overall approach of hiring execs, it has to be a unanimous hiring decision in terms of the focus on the loop? 

Gretchen Howard: No, sorry to clarify. It does not have to be unanimous, but I think there has to be a good enough discussion that people feel comfortable with moving forward and feel like this person would be successful.

So it's not a, you know, lateral decision and we have hired some controversial people where there are some that were so supportive and others weren't. And at the end of the day, we've got to trust the instincts, but I was stressing. All of the input is incredibly important. So more likely than not, we usually have universal support, especially an exec candidate.

There's not a rule that says you have to have unanimous 

Brett Berson: And so on this point. Gretchen, in terms of running a debrief on an executive loop, that's just been closed. Can you talk a little bit about how you structure that time and what that looks like? 

Gretchen Howard: Sure. We recently hired a chief security officer and we.

Definitely had people. Who are subject matter expertise in security on the interview loop. But we also had key partners like the engineering lead, sir, beyond the loop as well. And at the end of the day, this person was going to report to our CEO Vlad. So at the end of the day, it is his call. Now Vlad is a learner he wants to hear from all his leaders.

He wants to understand how this new function is going to interact. How. Not only how this person is going to go deep and what their vision is to building out our security org, but also how this person will work across the different functions and how they will contribute to the overall Robinhood leadership team.

So we usually structure the conversation or the debrief with everyone sharing their thoughts and usually. And manager in this case Vlad going last so that we don't bias the discussion and it's not overly structured, but we do. It's asking a lot of questions. It's pressure testing, people's assumptions.

And it's thinking through scenarios that may come up in the future. And how would this person, how do we think this person would adapt to it? So we go back and we look at, okay, what attributes did we prioritize when we were trying to hire this person? And how has. Specific candidate matched up or not matched up.

So it's a very fluid process, but it gives everyone a great sense of what does success look like for this person and what do we all have to do as a leadership team to make sure once this person joins he or she has set up for 

success 

Brett Berson: on that point? What advice do you have for new folks that are maybe joining your executive team for the first time?

A friend reaches out to you. And after spending the last seven years at company acts, they're joining us, the chief product officer at company Y and they want your advice on how to make that entry and that onboarding experience the most successful, or what can they do to increase the odds that they have a lot of success at this new company that they're joining.

Gretchen Howard: I think it's different for every role, but I think there used to be this old adage that was come in for the first 30, 60, 90 days. You just listen, be an active listener, but don't actually start making decisions. I actually think that's inherently wrong in a, especially a company that is a high growth, high velocity, high quality expectations company, like Robinhood.

So what I try to do, and I think it's made people successful. Yeah. First prioritize the relationships here, all the people you need to meet, build that trust. Start that communication, learn about them. Personally, learn about where they came from, learn about why they're here. That is the basis for everything.

So your first two weeks are all about that, but very quickly after that, you get to know your team. You get to know some big things. They're trying to solve, figure it out. Can enable them to have a quick win and the quick winch should not be about them, but it's in the service of something else. Maybe it's in the service of the team.

Maybe there's a huge pain point that you could eliminate for them. Maybe it's a great customer win or change or product change that you could identify through research and, and change, but have something where they actually can take action and show that they're like part of this company. I think that not only gets.

The leader, a lot of confidence, but it's a signal to the rest of the employees like, oh, they're in this, they're one of us they're aligned to what we're trying to do. And, and they're starting to take action. So I'm a big fan of doing that. Another piece that we do at Robinhood and we're, we're actually going to build out more of, this is something I really appreciated when I started.

The first week was all about listening to customers. So I think the first day I was there out of orientation, I went to our employee focus group with our research team. So it was listening to customers. We were previewing a new product with them, but it was amazing to have that culture sort of smack me in the face on day one.

Then I went on to sit with our customer support team, listen to more to customers. And so when a lot of companies say. Oh, we're customer first or our value is what radical customer focus. But if you actually bring that to life for your new employees and not just leaders, but all employees, I think that walking the talk is incredibly powerful.

If done. Correct. 

Brett Berson: I wanted to switch back a little bit more and close the loop on a couple other key recruiting questions as it relates to building the exact team. And one was, we spent some time going through the process that you developed. I'm curious, what do you think is required of a founder and CEO to be successful?

Building an executive team? 

Gretchen Howard: Yeah. I mean, I think one of the reasons I think Vlad will be one of the all time great CEOs is because he has a lot of self-awareness about what he's good at and actually where he likes to spend his time. And also where. He can have the most impact by spending his time. So I think he probably could have done my job.

He could have done lots of the executives jobs probably better than all of us, but he knew to keep reinventing himself as a CEO that he had to bring in leaders with very different focus areas, different skill sets, so he could continue to elevate himself and reinvent himself every six months. Company and gets larger and larger and gets more and more complex.

So I do think you have to have that self-awareness and that willingness to let go, too. I think in early stage companies, CEOs and founders are involved in every single decision. As a company goes through. Hyper growth becomes more mature. You really have to think about where do I spend my time and what decisions are important for me to make.

We went through this exercise pretty early on in my time at Robinhood, where we actually took yellow stickies and we put it on the wall and we categorized different decisions. We were making based on the complexity and the cost associated with them. And it was everything from. What size screen should an engineer have at their desktop to a strategic decision about launching a new product or going into new geography.

And what we found was at the time the co-founders were making all of the decisions, whether they were highly strategic, highly expensive, or they were very small in nature. And so by going through that exercise, It actually became clear to us that we had to be very thoughtful about where we spent our time.

And also we had to send the signal to the employees that we trust you to make these other decisions. So pushing that decision-making into the organization into different levels, into different functions. I think that. Is a lesson that is really critical for, especially for founders who stay as CEOs and scale with the companies, they have to learn how to let go and trust and focus their time on the most impactful areas.

Brett Berson: Is it mainly with like an exercise like that, that somebody can increase the chances that they're able to do that successfully? Because I think it's tricky to say just empower people and let people make decisions. And so there are other structural things or. Put another way a CEO reaches out to you and says, Hey, I've gotten a lot of feedback that I'm not willing to let go.

What should I do? I assume maybe you have an idea or you could bestow something other than no, no, no. Just like. 

Gretchen Howard: I think, yeah, it's a lot more complicated than that. It's not solved. I don't mean to imply that it's solved through a simple exercise. I think that over time, the first stage is as being okay and bringing in other leaders.

So when Vlad and Baiju brought in Jason as the CFO and me to run operations, that was a signal where they said, okay, We're going to still concentrate on engineering and product and these other functions that are really important. We are going to try to give them to these other leaders. They didn't know.

They took a bet on us and we had to build the trust and earn that respect from them. So part of it is building those relationships. Once they saw us an action saw, we built that trust. We had that authenticity. We had the great communication. The leash got longer and longer, which I think is a healthy thing.

And they saw, they were able to spend more time on areas where either they had more expertise or they thought were more impactful to the business. I think that's the first phase. The second phase is then that second level of leadership. When you say, okay, now we're even bigger. Do we need a head of engineering?

Do we need a head of product? Do we need a head of security? Do we need a chief people officer? How do we actually make sure that. I can still be involved in these strategic decisions, but some of that day-to-day management, second level problem thinking actually can be handled by someone else. I do think that there's questions on like there's employee level decisions, there's product level decisions, then there's decisions that will affect the entire future of the company.

If the CEO is not focused, the majority of the time on decisions that affect the trajectory of the company. Then it's an exercise they need to go through to say, is it the highest and best use of my time, but you can't do that without spending the time to develop the relationship with these other leaders and building that trust.

It just won't work without 

Brett Berson: one thing we didn't talk a lot about is do you leverage projects or exercises as a part of the loop when you're hiring a senior exec to join your executive team? 

Gretchen Howard: Occasionally I have mixed, I have mixed views on. 

Brett Berson: I love talking about things when someone has mixed views on it.

So I'm curious to hear what you've learned or how you use it as a tool, or maybe you don't 

Gretchen Howard: I've experienced and tried having people create presentations, run us through a meeting. We give them a brief, how would you solve this problem? And instead of doing a straight interview, we make them do a lot of pre-work and.

Sometimes I've seen that work. And sometimes people are really just really good presenters. And the reason I have a problem with it is because Robinhood is not an environment where we do a lot of presentation. We're almost at a point where we're going to band slides altogether. We're really all about writing out documents, having complex debates, asking a lot of questions.

And so. Giving someone an assignment and having them present to us just as one person, doesn't really give us the signals that we want. I think it is a useful tool in that. I do think just an interview alone has bias to it in problems, but maybe it's me. Maybe I haven't crafted the right exercise to give me the signals that I need.

So I have mixed reviews about it. If you have any ideas of great exercises, I'm all ears. 

Brett Berson: It's the topic that I'm really interested in, in. The short take in the studying that I've done is it's the most valuable project or work product, or what have you, is the thing that most similarly reflects the thing that the person will do.

And I think in the case of execs, it's a little bit. Harder because to your point, if you're not doing a lot of slides and presentations, then that's not what the execs doing. So in in fact it, it tests for something that you could care less about and unlike an IC role, you know, you're hiring a content person, you could have them go right and do the exact job.

And so I think it's a little bit trickier. I do wonder if there are. For very senior folks, if there's basically a job simulation. So if it's a lot of written based work or what have you, is there something sort of analogous to the actual job that would be useful or you could simulate something that you're actually working on together and to your point, a lot of the most senior folks at fortune 1000 companies technology.

Are very, actually good at presenting. That is a currency is like charisma and presenting. And there's a lot of people that get really far when there's a lot of sizzle and very little steak. And so you're almost testing them for a thing that in some cases may be the least valuable thing or the most fraught with correlation between like that thing and success in the job.

Gretchen Howard: Absolutely. So I think there's probably an inverse correlation with good presentation skills and success at Robinhood. Right. It's not something that we value. I think where we've found success is less. So in an executed brief, like here's an assignment or a thought problem, come back and present to us.

It's more in the conversation with. Hey, here's something where we'll take real problems. Here's something I'm thinking about or here's something I'm struggling with, or here's a product idea that we have, of course, under NDA. How do you approach this? How would you break this apart? Like be a thought partner with me.

And I think those type of exercise, they're very conversational and it's very back and forth, but if I leave a conversation and I learned something from that person, That's somebody I want on my team. I don't need them to have all the answers, but I want them to make me better. I want them to push my thinking.

I want to have an amazing thought partner with me on this journey. So I really appreciated those kinds of conversations, more than a formal exercise when I'm hiring executive. 

Brett Berson: Yeah, that makes sense. And then that, I assume that's the way that you collaborate with a lot of the folks on the executive team.

So it gets at like, this is an interaction that we're going to have all the time. And so if we can do that before you get hired, I can get a feel for that. One thing we didn't talk about in terms of like the underpinnings or parts of the process is reference checking. And I'm curious what you've learned about that and how that's a part of the way that you run a recruiting process for.

Gretchen Howard: It's an interesting question. And I'm sure fraught with lots of legalese that I won't get accurately. But I think with seasoned executives, there's always going to be people who love them and other people that they probably didn't land with. So I think you have to be really careful in reference checks.

I think you have to be pretty precise in what you ask and who you ask and go into those conversations with sort of eyes wide open. I think a person may have been in the wrong environment or might have been in a role that wasn't best suited for their talents, or it might be a bias perspective from a role that they had.

It might be outdated and maybe they worked together 10 years ago. So when people evolve and change and improve. So I think it's important to. Get other points of view. I really do, but I always, I try not to put too much weight in them as well. I think it's a good check and balance to have, but I tend to give the candidate the benefit of the doubt as well.

Brett Berson: Can you give an example of some of the stuff you might ask in a reference that you found useful as you recruited in your career?

Gretchen Howard: I really, when I do reference checks, I really keep it quite open. So I really try to. Ask the person about how closely did you work with this person? Would they be in your top 5% of people you'd want to work with again and any pros and cons?

I would give them context in the role in any pros and cons that person could provide. That would be useful context for me to have. So I leave it quite open and I really. Try to only do reference checks or put a lot of weight into reference checks with people that I know and trust pretty deeply. So it's also, I think there's the interaction I think, with the employee base, but in some cases, for example, some of the roles like.

For it's. What is their relationship with the regulators? Do they have a strong relationship? Are they respected? Do they have that trust? So especially in financial services, that's a different type of reference check. It's not just all about how do you work internally, but what is your external reputation?

Are you viewed as someone ethical and trusted? And are you recognized as sort of an industry expertise? So that has been one that's been particularly useful in this. 

Brett Berson: One of the interesting things. And you mentioned this at the start of our conversation, is that prior to Robinhood, you spent over five years helping build what is now called capital G.

Do you think there was anything in terms of developing an investment lens or seeing the world through the eyes of an investor that shows up in the way that you think about company building? 

Gretchen Howard: It's interesting. I think one of the metrics that we always looked at with our portfolio companies was LTV to CAC.

So lifetime value over customer acquisition costs. And actually it was one of the things that actually attracted me to Robinhood. There were many things that attracted me to Robinhood, but one that metric in particular, it was, I knew this company has such great product market fit and the CAC was so low.

Almost magical. Like I almost didn't believe it. And so I had this insider sort of knowledge knowing their financials before I joined, but it was something that I think is still really important as we think about scale and growth. How do we. Run a very lean operation that can support huge cost, not only huge customer growth, but then huge swings in transaction volume.

You know, we have unprecedented in transaction. Someone will tweet something and our crypto volume will 10 X overnight. So we have huge scaling challenges. And how do we make sure that we can scale and keep our. Extremely low, mostly by automating with technology. So we can pass that savings onto customers.

I think running lean, keeping our operations as automated as possible and having that customer focus. So it does show up in metrics like LTV to CAC, I think was a really powerful connection for me. And it made me think about, wow, I can have an impact on this very important metric that is assigned. Of the health of this business.

So I think there were a lot of important lessons from my investor days that have been valuable at Robyn. I 

Brett Berson: guess one final question that jumped to mind. Do you have a theory as to, as to why you think you've had such success in your career, if you were to sort of diagnose or go back to first principles about something about yourself, do you have a theory of, what's been the underpinning of this incredible career that you've had?

Gretchen Howard: I don't have a theory. Um, I would say I've been very lucky to be in environments that have charted new territory and where I've learned things. I think that not being afraid of. Not knowing all the answers or being a perfectionist has helped me. I think I was a history major in college and my first job out of college was actually coding and see, which I didn't even know how to turn the computer on.

So I wasn't one of those people who said, I want to be X when I grew up. I really didn't know. And so for me, I had to put myself in situations where I learned. By doing. And I learned by trying different things. And over time, I sort of figured out where I could add value, where I could have impact and areas that I wasn't good at it as well.

And so for me, it was very much a trial by error, but it was one of those where there's probably some luck involved, but there was also a lot of effort. So I don't have a theory. Other than that. 

Brett Berson: Oh, well, thanks for sharing. And thanks for spending all this time with us. This was fantastic. 

Gretchen Howard: Thanks for having me, Brett.