Assembling an Executive Leadership Team is Daunting — Let Thumbtack’s CEO Help

Assembling an Executive Leadership Team is Daunting — Let Thumbtack’s CEO Help

Recruiting and hiring executives is difficult for any leader, but especially first-time or early-stage founders who may not have enough knowledge to test candidates for skill in their area of expertise. Thumbtack CEO Marco Zappacosta has been there — and has a roadmap that'll help.

CEO and Co-founder Marco Zappacosta launched Thumbtack after graduating college. Like most first-time founders, he wanted to reinvent everything. Since then, his company has changed how consumers connect to local professionals, with millions of projects completed across the United States since the company started in 2008.

One of his proudest accomplishments, however, was not an innovation, but a realization — one that took nine years to fulfill to his satisfaction. “We've recruited heads of engineering, product, marketplace, finance, HR, operations, marketing and general counsel. For the first time in our history, we've filled all the seats. They're incredible in their own ways and work well together,” says Zappacosta. “It took a bit, but I’ve learned to leave reinvention to our product, not its guardians. I’ve realized how immensely valuable it is to have an experienced executive team.”

For the first-time and early-stage founder out there, it can be daunting to recruit and hire executives — especially when you don’t have enough knowledge to test them for skill in their area of expertise. In this exclusive interview, Zappacosta shares his four-step process for identifying and vetting his leadership team. From job descriptions to interview questions to references, Zappacosta shares his approach to changing up executive searches to generate a stronger signal for better leaders. Any startup will benefit from his thoughtful choices and techniques on evaluating senior executives.

“First-time founder, you may be the first to bring your product to market. But you won’t be the first to build a big engineering team. Or build a brand. Or run HR.”

Senior Engineering Director at Google. Director of Product Management at Youtube. Principal at Bain. When Zappacosta looks at the pedigree of his executive team, they are not only all impressive, but some are far more senior in their career than him. So how did he find, recruit and hire them? “In all honesty, we’ve made all the mistakes. We’ve definitely been enamored by background, thinking candidates had all the answers. We’ve over-indexed on skill and under-indexed on fit,” he says. “Hiring execs is extremely high beta. When it goes well, it can be an enormous force multiplier, accelerating your company in ways that you won’t appreciate right away. The flip is that a high-upside hire is also a high-stakes hire. It can take four quarters before you can really know if it’s going to work out.”


Like most companies, Thumbtack’s executive interview process typically starts with a recruiter doing a resume screen upfront. It’s a first-level filter to establish that a candidate plausibly has the right set of experiences. But Zappacosta has made one tweak that has fine-tuned this first filter — and it’s made before a single applicant enters the funnel: the executive job description.

1. Constrain your JD.

A big mistake that Zappacosta sees with with exec searches are the extensive job descriptions. “How many times have you seen a JD that defines the position by listing a dozen different skills? Don’t describe the entire position in exquisite form, even though all those skills may be useful. That laundry list of requirements won’t exist in a human,” he says. “Invariably you end up with someone who’s mediocre at all of them, but not exceptional at the ones at which you truly need them to be exceptional. You hire for lack of weakness rather than for an explicit strength.”

At Thumbtack, hiring plans — from executives to entry-level hires — are focused around identifying and evaluating the three most essential skills to the role. “That practice forces a few things. First, a hiring manager must think more critically about what she needs at that juncture on her team. Second, it keeps her from optimizing for every desirable attribute,” says Zappacosta. “So for an executive, here’s how this might look in practice as a summary: ‘This role will be expected to grow the team from 20 to 200 — so they must spike high on team-building, recruiting, and mentorship.’ That may mean that they’re less technically deep in another domain. But we can live with that. And we’ll solve for it by hiring other great people.”

This level of focus also serves the reference check process, which Zappacosta touches on in more depth later. “Instead of saying ‘Hey, tell me about this person and what they’re good at,’ you can orient it strictly around the attributes you’re evaluating,” says Zappacosta. ‘The line of questioning becomes more specific: ‘Hey, I'm looking for a team builder. I'm trying to find someone who could help us grow from 20 to 200. Can you talk to me about what you saw in her as a team builder?’ This elicits more concrete, targeted feedback.”

2. Split your interview process to separate skill assessment from fit.

After a recruiter does an initial screen for those specific attributes, the candidate is introduced to Zappacosta. Here he’s also made some changes to the executive search process that has made it more productive in building out his leadership team at Thumbtack. He starts by splitting what is typically one interview with the founder or CEO into two sessions.

He suspects that most founders won’t do this given it requires more time and coordination between very busy people, but he’s found the practice to pay dividends. “The first conversation is just to get to know the person. The candidate typically has lots of questions about us and she’s asking me many questions about Thumbtack and me. There’s ‘selling’ both directions to see if there’s interest,” says Zappacosta. “The second conversation tends to be more substantive. We start to unpack some of the experiences they've had. We get down to brass tacks on the position, including its challenges and opportunities.” It’s in this conversation that Zappacosta gets deeper on “fit.”

Interview questions for that first meeting are specific to the company, CEO and candidate, so those are more general informational sessions to get the lay of the land. But Zappacosta has tested out a number of questions to get at ‘fit” during the second interview. “I take a broad view of fit. It certainly means aligning on values. But also on ambition, how they like to work, how they view leadership and building teams,” says Zappacosta. Here are a few interview techniques and questions Zappacosta has used to evaluate executive candidates.

  • Name the job after this job. “A big one is ambition. How ambitious are they—and does that ambition map to that of the business? You need to know how that will connect with your personal ambition and what the company can offer,” says Zappacosta. “Ask candidates: what do you want to have happen to the business? If the candidate’s ambition is to sell to Google and mine is to go public, then we’ll be at loggerheads at some point — and in tension until then. It’s not about one person being right or wrong, but having two futures of the company. Plus, execs recognize that the reality is that it's not going to be the only job they ever have. So, you want to know how this factors into the career that they’re building toward.“
  • Find the invisible hand. “It’s critical to know what drives people. Some execs are motivated by money. Others by impact. Or the desire to lead high-performance teams,” says Zappacosta. “If you ask someone what motivates them, you get spoon-fed a pat answer. Ask: What accomplishment are you most proud of in your career? Answers to this question surface value systems. I might hear: ‘We had this huge stretch revenue goal. Nobody thought we’d hit it—and we did hit it.’ But I’d rather hear: ‘We were given this tough challenge. I rallied this team. We worked super hard. It actually failed, but we all looked back on it as an inspiring and motivating time.’ Again, one of these is not right or wrong, but it shows me a source of pride.”
  • Show me a worst. “Anybody who has worked for decades has failed immensely at some point. And if they haven't, I wonder: have you been through enough? Or are you not willing to be raw with me? Or are you not self-aware? It’s typically not a good sign, if they can’t talk about big missteps,” says Zappacosta. “Because talking about failure gets into the question of how vulnerable they’re willing to be, and if they’ve had transformative, first-hand learning, which happens after mistakes. So ask: ‘What failure are they most proud of?’ I want to work with leaders who are willing to be vulnerable quickly.”
“A misevaluation of fit, much more than talent, is usually the reason executive hires don't work out.”

3. Backchannel to assess skill.

If the two interview sessions give you a stronger understanding of interest and ‘fit,’ references and backchanneling gives you the data you need on their skills. “Once I wrap up the second conversation with a candidate that will continue on, I tell them that, in parallel with their meetings with other team members, I will start to be asking people about them,” says Zappacosta. “There are two important parts to this approach. First, I’m upfront about it and we take care to manage sensitivities with their current employer and a candidate’s timeline. Second, I don’t ask for references. I tell them that I believe the interview process is about mutual interest and fit, and that I want to hear from people in your past about your strengths and weaknesses. I tell them that I’ll reach out to various people. The best answer? ‘Awesome. Talk to everybody.’ But many clam up or preface how there are two sides to every story, which of course is true.”

The reason Zappacosta takes this approach can be traced back to one person in particular: Peter Currie, the former CFO of Netscape, “I asked Peter — and lots of executives since — if they trusted their gut more or less when it came to hiring, particularly comparing the end of their career versus the beginning of it,” says Zappacosta. “And 100% of the time I’ve heard: ‘I trust my gut less and references more.’ So, at this point, when it comes hiring execs, I tell people I’m assessing for fit, yes, but references will help me confirm that you have the skills and aptitude needed for the role.”

Zappacosta then talks to not two or three references but 10 to 20 people that he draws from various stages of the executive’s career. Historically, Zappacosta has spent as much time on interviews as he does with references. So if he’s spent 15 hours with a candidate, he’ll spend the same amount of time backchanneling. “You want a holistic view, so you look to talk to peers, managers, and reports from the most important years in their career. I ask about their experiences with the executive to understand the shared context. I want to understand how this person spent their days. Where did they spike? How did they help create leverage for the business? As much as possible I’m looking to learn exactly what they uniquely contributed and how well they worked with others.”

Here are some other questions Zappacosta asks:

  • How was this person perceived by others? This is better than asking “What did you think of this person?” because the reference is more likely to be honest, making it easier for the interviewer to audit the answer.
  • I’ve talked to three other members of the executive team at this company and they all called out this issue. What’s your read on that? This question gives references permission to be honest about red flags or faults.
  • What haven’t I asked that if you were me you would want to know about this person? This question gives references free license to say what they’ve wanted to share. This is often a good question to ask in the middle — versus the end —  to “unlock” other conversations.
  • If this person's on the executive team of a company you're thinking of joining, would that make you more or less excited? This question helps place the reference in the actual hiring decision — and potentially answer more honestly.

Notably, the process of speaking to references is not one-off, but cumulative in nature. “I also build my set of references from each reference. So I'll ask everybody, "Hey, if I want to be convinced that this is the best possible person to hire, who should I talk to? And if I want to convince myself this is the wrong person to hire, who should I talk to?’” says Zappacosta. “My point is not to dig for dirt. Every executive who has had a long, storied career will have something that they wish they could change. I'm not going to ding somebody for those things. But I want to understand the range of the spectrum from the best to the worst.”

As a reminder, during this time, the candidate is not in stasis. This backchanneling is all happening in tandem with the candidate meeting with functional heads, direct reports, and board members. This allows Zappacosta to get more signal on fit from a broader group of people. “The prompt I give to all the people meeting with the candidate is: ‘Was an hour conversation too short of a time with them?’ I want to know if they felt like the ran out of time and that they want to spend more time with them. That’s been a good proxy. But ultimately, it’s just an input. I tell everyone that these executive hires won’t be decided by committee. I mention that I want to make sure they will be a fit here, but that I will make the final call.”

Sure, I backchannel to confirm candidates’ skills. And I want the exec’s take, too. But most of all, I want to know how comfortable they are stepping in front of the mirror.

4. Present results of references and swap 360s.

The final and most personal part of the executive interview process happens at the end. Zappacosta arranges another meeting with the executive and presents a summary of his findings from his self-selected reference checks. “I’ll tell them that I spoke with people across different companies and domains, and we go through each theme for areas of excellence and improvement. Take note that you’ll get a wider band of feedback here than was discussed in any interview,” says Zappacosta. “My question for nearly each section is: ‘Why do you think I heard that?’ I’m listening as much for the answer as I am for how the candidate responds. Are they defensive and try to explain away the observation? Or do they say something like, ‘This is what I've been working on for a long time. I'm not a natural public speaker. And, as my role has grown, that has become more of a necessity. I’m more comfortable in small groups, but I’m taking a more active role in All Hands and sign up for a few conferences a year.’”

To put candidates more at ease — and make the evaluation bi-directional — Zappacosta offers his latest 360° review. “One of the last things I do is I share my most recent 360. I give the person a copy so they can see where I hit the mark and what I’m working on. It’s a gesture of my willingness to be completely open. I tell them to ask any question,” says Zappacosta. “For example, one thing that I bring up if they don’t is how I've always gotten feedback that I need to give more praise and recognition. I don't do enough of that. I’m working to make that better, but an executive shouldn't be surprised by it later. And, more so, those who know they need words of affirmation to be productive and happy may take note and speak up.”

After answering any questions, Zappacosta makes an request of his own. “Then I ask them what their current team says about them. It can catch people off guard and make them uncomfortable, but no one has said no. It really gets to their self-awareness and ability to be vulnerable,” he says. “We all have strengths and weaknesses. At this stage of the process, the truth is that we’re stepping into a reality of what it would look like working together. So it’s critical that we can share and exchange at this level.”

Even the most talented people have gaps. That’s why I share my 360 with executive candidates — and ask them to reciprocate.

If at the end of this executive interview process, there’s not a match or personalities clash, it’s not the end of the world. “Here’s the nice thing about interviews for your executive leadership: the stakes are high enough for candidates that at this point they're not trying to force fit,” says Zappacosta. “They have the capabilities and credentials to work many places — it’s not like they’re going to be unemployed. What they do want is a job where they can be successful and happy. This process has really helped suss that out.”

At this point, Zappacosta also takes stock. “It’s a good sign if, after all these conversations, that I feel as if I've bonded with this person.” says Zappacosta. “It's less about the specifics at this stage and more about the direction and nature of our interactions. Is it getting more vulnerable? Is it getting more intimate? Does it get more comfortable? For the leadership team I’ve hired, I’ve said ‘yes’ to each of these questions.”


Hiring people is at the top of the most formidable and frequent tasks a startup must do. So when it comes to a leadership team, the stakes are even greater. The confidence that allows founders and CEOs to launch and lead teams can backfire when it comes to gauging and measuring other leaders’ capabilities. First, constrain your job descriptions to the most critical three skills needed. The founder should split the first interview into two, taking care to separate skills and fit. To truly gauge skills, ask others, not the candidate. Let the executive know you will backchannel and spend as much time with references as with the candidate. Then present the good, bad and ugly back to the candidate and go through each area one by one. Then turn the spotlight on yourself and share your latest 360 review. Field any question. Ask your candidate to share her 360 review as well. Ultimately, you want evidence of someone with whom you can be victorious and vulnerable. Many people will have the chops, but this process helps establish whether there’s a genuine fit.

“Undoubtedly, first-time and early founders can find it really intimidating to evaluate seasoned professionals. That’s because, like many other areas as a leader, you don’t know what you’re doing. It’s paramount to acknowledge that — at the very least to yourself,” says Zappacosta. “Put it this way. If you met a professional chef who'd been working in kitchens for two decades and you were asked to assess their abilities, you’d very quickly say, ‘Hey look. There's no way. I don't know. I can't do it.’ And yet, most founders don't do that when it happens for roles they hire for. They assume they can glean what it takes to evaluate a product leader, head of engineering, or people ops executive. That’s patently false. The good news is that this is a process that can be learned and applied — and, when you get your rhythm with it, you can assemble a set of leaders that you not only gel with, but who’ll also change the trajectory of your business.”

Illustration by Alejandro Garcia Ibanez.