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

 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.

 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.

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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. 

 Thanks for having me and this'll be fun. 

 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.

 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. 

 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. 

 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.

 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.

 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. 

 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. 

 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.

 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? 

 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. 

 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.

 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.

 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.

 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.

 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. 

 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. 

 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.

 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 

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

 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. 

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

 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.

Gretchen Howard is the COO of Robinhood and former Partner at CapitalG, Alphabet’s investment fund. She covers the ins and outs of building your executive team — from developing the profile and recruiting to interviewing and onboarding.

Robinhood COO Gretchen Howard shares her executive hiring playbook

Gretchen Howard, COO of Robinhood, covers the ins and outs of building your executive team — from developing the profile and recruiting to interviewing and onboarding.
