Building Thumbtack: Five learnings in five years

These past five years have brought with them some of the most difficult, interesting, and rewarding moments of my career and life. In 2011, I dropped out of business school at Stanford to join an eight-person startup where no one was paid a salary, and helped turn it into a $1B+ company, changing how a $700B piece of the American economy works.

As I prepare to leave Thumbtack full-time at the end of the year (I’ll stay on as an advisor), and hand product leadership over to Noam, I want to share a few of the things I’ve learned about building a fast-growing product and the talented team behind it.

1. Some chaos is good.

When I started, I tried to make everything as orderly as possible. I’d go home frustrated if we weren’t working on the optimal projects. I didn’t want to waste one minute of our small team’s product-building capacity.

This drive for optimal efficiency backfired big time. Engineers revolted and pushed for holacracy. Feeling attacked, I nearly quit.

Quickly, however, I realized that less structure is part of what makes working at young startups so fun — so creative. Having things too planned is demotivating. Chaos creates space for new ideas that push companies forward.

An example: a change dreamed up by two engineers one night after a couple beers drove a 20% revenue increase.

So, how much chaos is good? Like most things, it depends. Successful startups go through phases: exploring and searching for new things, and executing when the path forward is clear. You want more chaos when you’re exploring, but there’s a place for it when you’re executing too.

2. Customer acquisition matters more than customer experience for early startups.

Thumbtack hasn’t succeeded because we’ve built the most beautiful, elegant interfaces. We’re here because we’ve cracked customer acquisition, largely through mechanisms we’ve built into our product. Early in a company’s life — especially a marketplace — having the best customer acquisition strategy is way more important than having the best customer experience.

Without people on both sides of the marketplace, we have no product. We’ve invested a large portion of our product development team in attracting customers and pros to our site, converting them, and getting them to stick.

Granted, this has come at the expense of building more features and beautiful experiences for our users. Even today I feel a bit like I’ve failed when I play with a competitor’s product and they have more elegant interfaces or more features — like the ability for a customer to pay a pro through the platform (which we still don’t have). But it’s an example of the hard trade-offs we’ve made to invest in growth, and it’s the reason we’re still here.

Plus, when your product team cracks customer acquisition, you then get to scale the team and continue to invest in growth while also investing in experience. Though ultimate word-of-mouth driven by a great experience is the way to reach true scale, early product focus on acquisition creates that pivotal slingshot.

3. Offering every service in every city wasn’t crazy after all.

The textbook advice for building an online marketplace would say to start with one category in one geography.

In the early days of Thumbtack, I questioned whether trying to build a marketplace in all 50 states for every service was the wrong approach. Lots of other people — inside and outside Thumbtack — had their doubts too.

The problem is, building a brand around one specific service isn’t likely viable. For the same reason the Sports Authorities and Circuit Cities of the world have lost out to the Walmarts and Targets, a broad marketplace is likely to win in our space.

On top of that, being broad from Day One required us to solve problems at scale from the get-go. Handing out fliers on the street wasn’t an option.

We had to re-write the textbook. We learned to build features flexible enough to meet the needs of diverse categories. We even built a unique team within our product organization — Category Management — to tailor the product experience for more than 1,000 unique services. Thinking big from the start was our secret sauce — and it worked.

4. Millennials demand a lot. (I know because I am one.)

Over the past several years, my job has centered on building and leading a team of now 50 product managers, designers, data analysts, and category managers. Almost all of these people, myself included, are at least borderline millennials.

What I’ve learned about my team and myself is that we have very high expectations for the companies we choose to work for. Thumbtack has to work for us as much as we work for Thumbtack. At its worst, it’s extreme entitlement. (Tip: Learn to screen for that in interviews.) But more often, it’s an authentic and productive desire to be better.

Here are some tips for managing millennials:

• Let us stumble: Small failures are humbling and satiate our desire to adjust and improve.
• Feedback, feedback, feedback: Constructive feedback enables our growth; positive feedback ignites our ambition.
• Inspire us: Show us how our work impacts our customers and the company at large.
• Lay out a career path: While this is hard in a rapidly growing company with immense uncertainty about the future, outline the skills a team member needs to progress.

The best way to knock the (entitled) Millennial out of a Millennial? Let them manage another (entitled) Millennial.

As a leader, my team of Millennials have really pushed me to up my game. As I look back on the threats to quit, the tears, the difficult conversations, the wins, the challenges, and the laughs, I realize how grateful I am for all of it.

5. Set a vision. And then don’t shut up about it.

As a product leader, knowing where your product and company are headed — and being aligned with your founders — is important. But knowledge and alignment still aren’t good enough. You have to communicate and evangelize a product vision that inspires a whole company.

I should have spent way more time on this, especially over the past two years as our team more than doubled each year. There was always a fire more urgent than this foundational work I could do to communicate a clear and compelling vision. But that’s not a good excuse.

What do I mean by a vision?

• It’s an inspiring, north-star to orient your high-level decisions.
• It lays out the big, concrete steps your company needs to take over the next few years to make it happen.
• It should be short, memorable, and framed within a broader technological or societal context that’s inspiring to your team.

Once you have it, don’t stop talking about it. Use it as the starting point for all product planning. Refer back to it in key company meetings. Make sure it’s communicated in onboarding. Put it all over the walls.

Focusing on your vision will help rally your team to do their best, most meaningful work. Don’t take that for granted.

Above all, what I’m taking away from my time at Thumbtack is the knowledge that building a great product isn’t about the successes. Building a great product is about all the mistakes you make while trying to be successful, and what you learn along the way. It’s also about the people who share and enrich the journey. Thumbtack isn’t the only thing that’s grown over the past five years — I’ve grown a lot too, and I’m so grateful to have had such a warm, smart, and inspiring team by my side.