The four ways I found help (once I learned to ask)

Five years ago I hadn’t built a marketplace nor a 50-person product team. Needless to say, I needed a lot of help.

The problem: I was too self-conscious to ask people who had done it, afraid of seeming weak or incompetent. (Research shows I’m not alone.)

The good thing: All of us love feeling needed and wanted. So, when you ask someone for help, they’re more likely than not to say yes. I just needed to learn to ask.

I now understand what help is out there, what’s most useful and how to get it. I want to share what I’ve learned so other young leaders can find the right help. I’ve structured this post around the four types of help I learned I needed.

1. Mentors & Advisors

These are a small set of people with whom you will develop a close relationship with and who will have a vested interest in the company’s success. I had one, but some of my peers had two or three to go to for advice on problems both broad (e.g., how to evolve your org structure) and tactical (e.g., a key team member has a compelling counter offer and is making demands).

Finding the right close advisors is a bit like hiring a key team member. I talked to more than 20 potential people over the course of six months before I was convinced I had found the right person. Investors were helpful in making suggestions and intros. The great folks at CapitalG even set up a dinner with 10 product leaders to enable me to “Advisor Speed Date.”

I was confident Parker Barrile was the right person for me after two conversations with him. We were very quickly able to have “high bandwidth” talks about key issues I was facing. With experience building a big product organization and a marketplace, he could give me solid advice. He had experience advising other product leaders. And he was excited to help. I knew if I felt like I was imposing on someone or fighting for his time, not only would he be hard to reach, I’d be reluctant to try.

Over the course of the last two years, we’ve grabbed coffee or lunch every two months. (We probably should have chatted slightly more often.) We also jumped on the phone when I had a time-sensitive issue. Despite experience building a marketplace, I’ve gone to Parker much more on organizational and process questions than on product questions. (It’s really hard to give product advice without intimate, day-to-day knowledge.)

Parker helps build my confidence as a leader by reinforcing that I have strong instincts and I am often on the right track. Pointing out what’s going well enables me to open up about what I’m really struggling with.

We granted Parker a small number of shares to thank him for his time. (You probably don’t want to work with someone whose help is contingent on compensation; on the other hand, you don’t want to take advantage.) He also signed an NDA, so we could share product and business questions openly.

2. In it together: Peers

I found that a group of peers — in my case other product leads — could help me on a similar set of issues that Parker did, less formally and frequently. These people are close enough to the issues I’m facing to quickly put themselves in my shoes but also have the experience and intuition to help me see around these corners. They’re also great people to vent to because they’re also facing similar frustrations.

The most helpful peers were people with significant product jobs at companies one or two steps ahead of Thumbtack. Jonathan Golden, a Director of Product at Airbnb, is one of these peers who was helpful because of the product parallels between Thumbtack and Airbnb; they often faced the same organizational challenges we did a year or two earlier. He was also a person I ran to at some of my most frustrating early moments like when a few engineers decided we didn’t need management.

This group of trusted peers developed organically for me, though I should have been more proactive about building this network. I met most of these folks through colleagues or friends who realized that we could be helpful to each other. Others I met socially. I generally grab coffee, lunch or a beer with these folks at least every four to six months.

3. Bring in the big guns

Like many companies, Thumbtack has some mission-critical product questions that we aren’t the first to face. We developed a stable of paid and unpaid advisors to help us create and refine our tactics. Interpersonal chemistry is much less important here. What matters is deep expertise.

I’ve invested the most in SEO advisors. Google is a significant customer acquisition channel for Thumbtack and we know there is huge potential. We have both advisors whom we pay (you could call these consultants) and those who we meet with informally for a two-way exchange of ideas.

For the top few issues like SEO and some key marketplace dynamics questions are for Thumbtack, it’s worth whatever time and money it takes to build and cultivate this network of specialized advisors. For an early-stage company, the right advisor can help clear a make-or-break hurdle. (I don’t think Thumbtack would be here without one such person.) For a growth-stage company, help on a leverage point like SEO can create hundreds of millions of dollars of value.

For paid topical advisors, we set clear expectations in the upfront contract about the cadence of interactions and any deliverables. The compensation to these experts was substantially greater than the small number of shares you might give ongoing advisors. We did a mix of cash and equity depending on the preference of the advisor.

4. Survey the experts

There are a bunch of key one-off decisions — often around organizational structure — that a growing company like Thumbtack isn’t the first to face. I find that having a handful of one-off conversations with companies that faced similar choices to be very informative in shaping my own decisions and giving my team confidence I was making an informed, thoughtful choice.

For example, two years ago when we realized we needed dedicated analytics people (previously analysis was done by the engineers and PMs), I wanted to know how best to build and structure that team. Through existing contacts and asking friends for intros, I met with eight analytics leaders at other companies. Understanding the war stories and successes of different approaches was instrumental in shaping our approach and how confident we were in that direction. (If you’re interested in the synthesis of what I learned on this topic, I’m happy to share it.)

Yes, this is time consuming. But it’s surely worth it if the issue is both significant and difficult to undo. Topics like starting a new team and expanding into a new product area where there’s significant up-front investment before you learn are good examples.


It took building confidence as a leader to open me up to help. Once that happened, having these “helpful” conversations became one of my favorite parts of my job.


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