Without a resume stacked with startup experience, the learning curve was incredibly steep for Zappacosta. Key to finding his footing along the 13-year journey of building Thumbtack? Knowing when to pull from established playbooks versus beginning from first principles. Here’s how he delineated between the two:
“Advice is incredibly valuable for tackling challenges that are commonly felt across similar companies. When it comes to G&A, recruiting or leveling, there’s a lot of infrastructure you can borrow from other companies who’ve done it well — you don’t need to be particularly inventive,” says Zappacosta. (But we'd note that we found plenty of innovation in his approach to hiring executives.)
It’s useful to recognize the ways in which you’re not a special flower. In the early days, you think you and your company are special in every way, and then over time, you realize there’s a lot of stuff that everybody goes through.
He points to where advice often breaks down: “You need to be very skeptical when advice is context-specific. When we were first building Thumbtack, basically every smart person we talked to told us that our category focus should be narrow instead of broad. I’m glad we didn’t listen to them, because we would have failed,” he says. “You started a business because you have a unique insight and think there’s an opportunity to do something different. That’s likely to mean a contrarian approach — whether that’s a product, business, marketing, or design strategy. Whatever it is, you need your own point of view and to trust your gut.”
But with a seemingly infinite amount of forks in the road on a first-time founder’s map, knowing when to tread on established paths is an incredible strength. With that in mind, in our exclusive interview with Zappacosta, he shares plenty of pages from the Thumbtack playbook that other startup leaders can borrow from. He pays particular attention to the areas that fall directly under the CEO’s purview, including getting the company culture right, refining your hiring process, and tinkering with your board meetings. These are perennially popular topics on the Review because nearly every leader out there is looking to make improvements in these foundational company building blocks.
Starting with company culture, he explains why applying the lessons from late-stage companies to early-stage startups is a big mistake — and what to do instead. He makes the case for revisiting your values so that they’re lived even in the company’s hardest moments. Zappacosta also opens up about some of his hiring missteps over the years, and how he’s architected the interview process to dive deep rather than just skim the surface with a candidate. Finally, he wraps up by taking us inside Thumbtack’s board room, and the tactics he uses to make sure board meetings have maximum impact across the entire org. Let’s dive in.
THE COMPANY’S CULTURE AND VALUES ARE AN EVOLUTION — NOT A DESTINATION.
Plenty of column inches have been devoted to architecting your startup’s culture, but Zappacosta believes these often skip over the critical foundational step. “When you read about culture-building, it’s all about explicit work — like defining the values. What that undersells is that early on the cultural attributes and values of an organization are really a reflection of who joins early on — the shared values that bring the early team together. Building the culture starts with who you hire, and it’s nothing more than that,” he says.
It’s a mistake to be too explicit about the culture and values upfront in the earliest days of a startup. You don’t know yet who’s going to be attracted to your idea or you as a founder.
Instead of viewing company culture as something etched in stone, Zappacosta shares the three phases of culture-building he’s seen Thumbtack go through — and cautions early startups not to skip ahead to phase two or three:
Phase 1: Emergent culture. “I started this business straight out of college, having never worked anywhere else. I didn’t always appreciate the impact one person can have on the vibe of the place. I wish I had known that more clearly and I would have been more maniacal about who we brought on in the early days.”
Phase 2: Defining values. “At around 50 people we started to scale from a headcount perspective and we needed to leverage others to interview candidates and assess culture and values fit. Those folks reasonably asked, ‘What are our values?’” says Zappacosta. “The second phase is a definitional exercise — you’re trying to take this implicit culture and set of values and turn them into something explicit.”
Phase 3: Aspirational culture. “It wasn’t until about 10 years into the business where I felt like we could treat culture and values as something more aspirational. It’s not simply a reflection of who you are and who you’re trying to attract, but who you want to be.”
Don’t overlook fit on the search for top talent.
Returning back to the earliest days of weaving the cultural fabric, Zappacosta admits that there’s a tricky needle to thread. “Early founders, myself included, tend to over-index on talent and under-index on fit. It’s so hard to recruit when you’re two people with no brand, no money, experience, or traction — that’s a tough sell. So you often hire the most talented or skilled person you can get,” he says.
Of course, talent and skill are bars folks need to clear, but not the only ones to consider. “Typically what causes relationships not to work isn’t a lack of talent, it’s usually a lack of fit. Looking back, most interpersonal issues don’t crop up because one person is smart and the other isn’t. It’s that folks have a different approach or different preferences for how to do something. It’s not right or wrong, it’s just left or right,” says Zappacosta.
When there’s high fit on the team, there’s high trust. And when the team has trust, you can move faster because you don’t need to go to the mat on everything.
He points to an early Thumbtack example to sketch this out more clearly: “My co-founders and I are very documentation-oriented. It wasn’t something we explicitly talked about in the early days — it was just how we liked to work. We hired on a really seasoned, sharp executive that was clearly smart and capable. But he just wasn’t interested in working with that approach,” says Zappacosta. “He chafed at being asked to operate in a way that didn’t play to his strengths or what he thought wasn’t the best way to do it.”
Defining (and re-defining) your company values.
Another frequent cultural misstep Zappacosta sees? Mixing up the difference between values and habits. “The word culture is used in these two different contexts. One is habits — like eating lunch together, a weekly all-hands, or an open calendar policy. Values are the ways you make trade-offs as a company, or work through tensions, and provide a cultural compass,” he says. “Doing weekly demos isn’t a value, it’s a habit or ways that the values are lived.”
Once Thumbtack hit the second phase of culture-building, Zappacosta and team began defining the values, and he includes some details on how this manifests throughout the folks Thumbtack hires.
Lead with why: “Is this person curious, and intellectually honest? Are they able to reason from first principles and is there written evidence of clear thinking?”
Make it count: “How impact-oriented and results-oriented is this person? Are they satisfied by simply thinking about things versus getting things done?”
Own it: “This is all about a sense of responsibility — people who feel they owe it to themselves and their team to deliver on their commitments.”
Choose teamwork: “There are people who like to sign their names next to their accomplishments, and then there are those who want to highlight the group effort. We look for folks who are excited about working with others and invest in each other.”
Say what you mean: “Is this person comfortable enough in their own skin and clear enough in their values to give feedback and be critical?”
But Zappacosta cautions founders that this is not a one-and-done exercise. “Originally, our first value was called ‘Reason from first principles.’ But we found it put too much emphasis on reasoning — which created an anti-pattern. That reasoning was being over-applied — there was too much debate around the why of something past the point of diminishing returns,” he says. “When we went through a second round of assessing our values a few years ago, we felt that ‘Lead with why’ spoke to the behavior that we wanted more effectively.’”
Recognize that how you frame and talk about values can lead to different implementations, and don’t be afraid to make changes as the business evolves.
Living your values in both the company’s peaks and valleys.
Another way to think about it is that values should shine through in the company’s harder moments, which Zappacosta felt acutely in 2020. “COVID definitely tested us in late Q1 and into Q2 of 2020. There were real fears about what it would mean for our business and how demand may be depressed. Because of that, we had to do a big layoff,” he says.
“One of the biggest questions is how you approach that hard choice for your company, and we took a value-centric approach. Nobody blamed me or the leadership team for COVID. The only real question was, were people going to gain or lose confidence in our leadership by how we dealt with it,” says Zappacosta.
The power in hard moments, despite how searing they feel, is that they’re ultimately very revealing. If you reinforce and live the values that you say you aspire to, it’s a moment where you build enormous trust and loyalty.
He points to Thumbtack’s first value, Lead with Why, to illustrate this point. “‘Lead with Why’ means that whatever decision you’re faced with, you need a point of view that’s grounded in some first principles. The day after we did the layoff, I gathered the team that was still on board and took them through the decision tree,” says Zappacosta.
The decision tree had three key components, which were shared with the entire company. “The first question we tried to answer was over what horizon are we optimizing for — is it 6, 12, 18, 24 months? We told them why we picked the number that we did. Next, given that, the second question was our expectations about what COVID is going to do to our business between now and that time frame. Here are the six scenarios we came up with, here’s why we picked scenario number four. Given scenario number four, here’s the gap we have between the current finances and what we need to achieve confidence in long-term viability,” he says. (As the next year remains uncertain and folks may be revisiting these estimations, we recommend leveraging our Scenario Response Template.)
As Zappacosta puts it, he laid it all bare for the company and trusted folks to receive that information — even if it was a painful moment in the company’s history. “It’s easy to support your values when it also supports your business. The challenge is how you apply them in hard moments.”
DURING THE INTERVIEW PROCESS BE A DEEP-SEA DIVER, NOT A SNORKELER.
Zappacosta has unpacked some of his exec hiring frameworks on the Review before (and it’s well worth a read or a re-read). In our latest conversation, he expands on some of those same ideas and adds new pages to the playbook by pointing out some of the most frequent missteps.
For starters, he points out a frequent mistake founders make before even setting up the first interview — getting greedy. “When you’re hiring a role, you make your list of what you want this person to be great at, and your list is 12 items long. What happens is you end up hiring for lack of weakness rather than exceptional strength in any one area — that leads to a mediocre outcome,” he says. Zappacosta’s tip? Push yourselves to define the role in terms of three specific key attributes that you want the role to bring, and gear your interview plan according to that narrow focus.
Always ask these two questions — and go deep.
In just about any interview with Zappacosta, candidates can expect two of his favorite questions. First up: What professional achievement are you most proud of? It may sound pretty standard, but it’s his approach that makes this one of Zappacosta’s go-to questions.
“I ask them to take me really deep, so it’s not just like ‘Oh I’ve grown a lot in my career.’ I want to hear the specific thing that happened at your job and why you’re really proud of it. I want to know what your role was and what you uniquely brought to the project,” he says. “I’m trying to get a sense for how ambitious this person is, how balanced they are in assigning responsibility for success amongst the team, and how honest they are with whether it was just up and to the right, or if there were challenges along the way.”
Zappacosta also holds back from rapid-firing through a long list of talking points. “I’m always surprised by how little interviewers probe. With the ‘Tell me about your biggest accomplishment’ question, I’m not all that interested in the headline. The real insights come when you keep digging deeper and deeper. I’d rather spend 90 minutes on one or two topics rather than asking 17 unrelated questions because you think you need to touch on all these issues,” he says.
You get more signals about someone’s judgment and thoughtfulness by pulling one thread all the way through.
He immediately follows that discussion up by asking: What’s your biggest professional regret? In his view, the power of these two questions comes from pairing them together. “Typically someone is riding high off the last question because they got to brag and go deep on something they feel really good about, so this next question often surprises people,” says Zappacosta.
He finds the response typically goes one of two ways. “One is the person says, ‘Oh man, there’s one thing that instantly comes to mind. It’s hard to talk about, I’m not proud of it, but I’ve been able to really reflect on it,’” he says. “Then we can go really deep and talk about what they learned. I’m under no illusions that I’m hiring perfect people, but I want to make sure I’m hiring people who are self-aware of being imperfect.”
But more often than not, he receives a different type of answer. “It’s often like, ‘Oh, I only got a B but I really wanted an A. Or this thing was only a modest success, not a tremendous success.’ It’s just one more chance for them to brag,” he says. “I’m very turned off by those types of answers. It means they’re either not self-aware, or they’re not self-confident enough to own their mistakes. That’s not who I want to work with.”
Choose your behavioral interview scenarios carefully.
Hiring execs as a first-time (or even seasoned) founder is a tricky hurdle to clear. “When you’re hiring folks earlier in their career in an IC role, you can audit their talent and output fairly well. But for executives, their output is decisions. The main thing you’re hiring for is good judgment, which is a very fuzzy and vague concept,” says Zappacosta.
To suss out judgment, he leans heavily on behavioral interviews — but he rarely uses Thumbtack examples in these scenarios. “I’d much rather have the candidate take me through specific experiences in the past rather than how they would react to a Thumbtack example. It’s easy to be miscalibrated when someone is speaking to something that you have infinite context on and they have zero context,” he says. “It’s easy to say that they don’t get it or they weren’t quick enough on their feet when you’re actually just totally not appreciating what someone with zero context is going to know.”
Don’t just check the box with references.
When it comes to hiring, Zappacosta has found that plenty of leaders treat references as an afterthought — a final box to check that’s somewhat of a formality before extending an offer. But for Thumbtack references are critical to the hiring process — if not more important than the interview itself. “Interviews and technical tests are often imperfect — they’re contrived, and they’re stressful in a way that regular work is not stressful. But it’s hard to fake something for 10 years across three different jobs and seven different reference calls,” he says.
He breaks it down between talent assessment and fit assessment. “When it comes to talent, I typically trust the market signal and the references. How has this person’s trajectory been? What do their peers and colleagues say about them? What successes have they been a part of,” says Zappacosta.
But when it comes to values, culture and manager fit, he trusts his gut. “I overweight our impressions of fit and underweight what the world tells us about this person — even if the references don’t highlight the concerns we have. Fit is as much about us as it is about the candidate. Just because someone is not the right fit doesn’t mean they’re good or bad,” he says.
Here are his top tips for approaching reference calls:
Narrow your focus. “Be really clear with what you’re trying to understand about the candidate so you can structure your questions accordingly. There’s nothing worse than starting with, ‘What do you think about this candidate?’ But when you ask a specific question like, ‘Tell me a time when you saw this leader build a new team,” then people typically let their guard down and share more details.
Read between the lines. “The reference likely knows and likes the candidate more than they know or like you, so you have to be attentive to the language people use. People are always careful and it’s a coded conversation so small words can mean a lot.”
Ask for more references. “I try to end each call by asking, ‘If I wanted to be convinced that this is the right person for the job, who else should I go talk to? And who should I talk to that’s going to tell me this might be a mistake?’ Be explicit about wanting folks from both sides.”
Trust the process.
Startups put tons of time and resources behind their interview processes — but a Thumbtack internal retrospective on why hires didn’t work out highlighted a key finding. “Interestingly, what ended up being an issue with the hire was almost always cited upfront in the interview debrief. That taught us an important lesson — it wasn’t that we were blind to X issue. But you spot things in the interview and you try to rationalize it away,” he says. “You’re trying to hire quickly, so you’re optimistic or you make a compromise. The problem boils down to not having enough conviction in the interview process.”
WHEN IT COMES TO BOARD MEETINGS FOCUS ON THE WHY, NOT THE HOW.
For first-time CEOs, there’s perhaps no meeting that comes with a mountain of anxiety and nerves quite like board meetings. There are piles of prep work ahead of time assembling the board deck before you even get to the meeting. Then you’re standing up in front of the room with your slides, trying to rattle off all the key points. It’s long, grueling and often inefficient.
“Founders can find themselves overrun by personalities with board members who have more experience and cachet. The most important thing is that the board doesn’t create negative value. New founders need to feel comfortable pushing back on board expectations and coaching people in a room when the discussion veers off track,” says Zappacosta.
Over the decade-plus of building Thumbtack, Zappacosta has faced these same stumbling blocks — he’s carefully honed his advice for other founders navigating the board room for the first time. He encourages founders to start by spelling out the three different roles the board plays:
Administration. “This is the easiest piece of the puzzle. Each board will have some amount of option approvals and minutes and other tasks to make sure the business is dotting the I’s and crossing the T’s. The key here is to make this portion of the meeting is efficient by being diligent in preparation and clear on what you need from the board members so you can clear through those line items.”
Accountability. “At its core, a board is about creating accountability for the CEO to deliver on an overall plan — and I think that’s super healthy. Does the board understand the commitments that are being made, by whom, and what success metrics look like? My suggestion is that folks present this in a deck that focuses on a small subset of the plan where there might be questions or concerns that need to be highlighted.”
Big strategic decisions. “This is where you should focus the most time in your board meetings. What are the important questions for the health of the business? An example from the last year is our post-COVID future of work plan. We had a strong point of view, but we wanted to make sure that our board stress-tested our decision. It’s not a superficial conversation where we just want them to read the plan and rubber stamp it. We want them to really wrestle with where we’re coming from. What questions are we not asking that we should be? What concerns do you have? This process really sharpens our thinking and makes us confident to take big bets.”
One of the biggest head-scratchers for first-time CEOs is figuring out when’s the right time to surface things to the board. “It’s not on day one of a project where you’re still trying to figure out up from down, but it’s also not close to launching where there’s no opportunity for real feedback,” says Zappacosta. “Consider where along the journey you have a coherent and organized point of view, but not so late that you’ve already coded and designed things.”
When presenting on a partially-baked plan, it can get the stomach butterflies fluttering in overdrive — and Zappacosta admits it’s a learned skill honed over time. “You’ve got to trust that they’re not going to question your leadership simply because you don’t know exactly how you’re going to do something yet. Being vulnerable with your board and letting them into your decision-making process is healthy and strengthens the relationship,” he says.
And when it comes to bringing points of discussion to the board, Zappacosta recommends a few key areas of prep. “The first question to figure out is what you’re actually looking for feedback on. With our future of work discussion, we didn’t want to get into the specifics of the implementation — like our real estate strategy or how we might adjust comp,” he says. “We wanted to focus on the risks and the trade-offs that we were making and if we had any blind spots.”
The next step is getting clear on the framework used to approach decisions. “The mistake is when someone brings something to the board without the context of how they got to that decision. Everyone comes from different prior companies and has personal points of view, so everyone needs to be grounded in the same framework,” he says.
You’re not trying to ensure that your board would do the exact same thing in your shoes, but that your board recognizes the trade-offs that you’re making.
Take the lessons outside the board room.
Those board decks that can cause so many founders grief? Zappacosta’s figured out a way to maximize their impact — by sharing them across the entire 800-person company. “It’s useful to leverage the board meeting for more than just a few hours every quarter and to instead be something with benefits more broadly. We use board decks to drive internal alignment by telling one story to everybody. You’ve got one set of concerns and priorities for the entire company, and it’s clear what’s on and off-track,” he says.
Having never worked anywhere else, my approach has always been to ask what I would want if I just worked here, not as a founder. Typically the answer boils down to wanting to be treated like a partner and trusted with all the context I need to do my job well.
Presuming good intent is key here. “Maybe one day this will no longer be plausible as the company gets bigger, but this has never caused any problems for us. You hire good people and they act in good ways and I’m always inclined to create policies that solve for the base case,” he says. “Too often HR or legal policies solve for the exception — but then you force everyone to operate in a worse environment simply because someday there could be a bad actor who does a bad thing. I’d much rather solve for the 99%.”
WRAPPING UP: BRING FOLKS WITH YOU ALONG THE JOURNEY.
Returning to one of Zappacosta’s favorite interview questions about his most proud accomplishment, we turned that same question back to him. Here’s what he said:
“The thing that I take the most pride in is that you could take a sampling of people over the last 10 years and you would see a real common thread. There’s a real consistency of values and principles and that investment and dedication to team and culture is something I feel very proud of,” he says. “I didn't come into this business with an amazing amount of experience or skill, so I believe one thing I've really helped do is attract amazing humans and engage them and retain them and bring them together to do something that collectively we never would have been able to do any other way.”