What I learned about hiring a Chief Operating Officer

Today, Sift Science welcomed Russ Fujioka as our President & COO. Russ helped grow Adobe from a $40 million company to a billion-dollar category leader, led enterprise efforts at Dell, and most recently served as President of the Americas at Xero. I’m thrilled to welcome him and his expertise as we rapidly scale our world-class solution for building online trust.

This is a meaningful inflection point for Sift. We’ve found product-market fit and it’s flattering to have someone of Russ’ caliber believe in our mission and our potential. Throughout the hiring process, I learned a lot about myself and our business. I’m documenting a few lessons in case it can help others.

It’s not about you

We’ve grown a lot this past year — more than doubling headcount, growing revenue more than 250%, and raising a $30 million Series C. We’re incredibly excited about our progress and direction. But this also prompted a real wakeup call for me — that we have to play to win, not just survive, in a very competitive market. The growth afforded me an opportunity to step back and reflect on my strengths and weaknesses as CEO. Instead of believing that you can/must tackle every scaling challenge, check your ego and embrace that it’s OK to look for help. Don’t take it personally — it’s about putting the business in the best possible position to succeed. As former GE CEO Jack Welch said, “The team with the best players wins.”

When to hire

When a company should hire a COO is unique to each business and its market, current team, competitive landscape, etc. However, I’d recommend a minimum amount of scale (I’d suggest $10M+ Annual Recurring Revenue) before searching for a seasoned business partner. For Sift Science, we’re also in a very competitive market with little room for error. I didn’t want to wake up a few years from now and regret mistakes that could have been easily avoided. While no path is without its bumps, I do believe that the right experience and wisdom can help smooth the road.

Who to hire

Once you embrace the reality you don’t know it all and feel that your company is at the right stage, you must figure out who the right person for the COO role is. In our case, my and the early team’s background is in engineering and product. I’ve also never worked at a company larger than 150 people. While I’ve learned a few things about go-to-market strategy and execution over the years, it’s no substitute for decades of experience. It was clear that we’d benefit from someone who’s been on a few rocketships and can help us see around corners as we scale the “business” part of our business.

Throughout our hiring process, I learned that COOs come in many flavors. Some specialize in turning around a sinking ship while others are experts in finance and strategy. I even met high-quality candidates who had run product and engineering. At the start of your process, before deciding exactly what you’re looking for, keep an open mind and meet with a wide range of candidates to understand the landscape of backgrounds and skillsets. It will help you flesh out exactly what you’re looking for and you’ll be more assured when you find the right candidate.

How to hire

Our search took seven months, a few months longer than I had originally planned. That’s okay. This is one of the most important hires you’ll ever make and a false positive is very disruptive. I ran a multi-stage process:

• Coffee with me
• Meet with subset of our executive team
• “Working session” with me (review past board decks and discuss specific challenges)
• Meet rest of our executive team
• Meet our board
• Dinner with me

If I decided the candidate should continue after our initial coffee, I was upfront about the entire process and made it clear that either side could opt out at any point. This all seems like a lot, but the stakes couldn’t be higher for both parties. This is also a huge decision for the candidate, and these touchpoints give them a chance to do their homework.

Finally, go deep and wide with references. You’ll learn so much more from these calls than from interviews. Not only do references help you make a more informed decision, they give you some sense of how to work well with the right candidate. I strongly recommend at least 3–5 backchannel references. If you can’t find an introduction through your network, try a cold LinkedIn message — I was pleasantly surprised how many folks responded.

Deciding

When it’s time to make a final decision, trust your gut. Don’t succumb to unconstructive pressures and fears. Ultimately, this is your decision. You’ll be working most closely with this person, and you are responsible for their success and failure.

In Russ, I saw someone with incredible breadth and depth of business experience — someone who can help us see around corners and reach our full potential. But just as important, his experience was tempered with the humility and collaborative mindset that we cherish in Sift Science culture. Going deep on my reference checks built even more confidence that Russ would be a cultural asset, cultivating the qualities we want to keep and raising the bar so that we can perform at our very best.

I’m thrilled to welcome Russ aboard, and look forward to learning even more from having a seasoned business partner on board than I did finding one.