Why Operator Collective Invested in SetSail

I didn’t realize it at the time, of course, but my 11 years at Salesforce set me up perfectly to become an investor. I saw firsthand the rise of SaaS and the subscription economy and worked with some of the world’s most innovative tech experts. Above all, and thanks to my years of leading the Salesforce AppExchange, I learned how to evaluate apps quickly, succinctly, and with a great deal of success.

Last year I joined forces with Mallun Yen at Operator Collective, a venture fund that focuses on B2B software. A former lawyer and Cisco VP who went on to build both SaaStr and one of the fastest growing venture-backed enterprise startups ($0 to $100M and IPO in 3 years), Mallun has also seen her fair share of sales productivity software, as well as founders and small businesses. Together, we’re uniquely equipped to evaluate startups.

As investors, we see tons of sales productivity apps and pass on the majority of them. But because we’ve seen what works and what doesn’t, you can be sure the few sales productivity apps we do choose to invest in inspire real confidence. SetSail was one of those — and it wasn’t just the technology that impressed us. It was also the backstory and the founders.

It all started at Google

For years, Mallun and I had separately been hearing murmurs about something big happening at Google: A group of machine-learning whizzes were changing how they incentivized their sales reps. Haggai Levi and Bert Lui were leading the charge, and their results were amazing: they saw double-digit productivity gains for several years straight.

How? By using AI and “micro-incentives” to reward deal progress. We hadn’t seen anything like this before and our curiosity was piqued. Soon the duo split from Google so they could fully immerse themselves in this premise.

Then came Dropbox

The more we got to know Haggai and Bert, the more interested we became. The learnings from the Google experience opened their eyes to all that was possible — but even more important was that they were able to expand upon that foundation with early enterprise customers like Dropbox.

Given how early-stage SetSail was, the team at Dropbox was especially rigorous in their assessment. Dropbox created a control group that would continue using the existing process, as well as a pilot group that would use SetSail — and the benchmarks they wanted the pilot group to hit seemed nearly impossible.

But the pilot team blew the control group out of the water. Using SetSail, they saw:

• +34% in weighted net new pipeline
• +67% in emails received from customers
• +37% in meetings booked

Yes, they saw a huge spike in emails sent and calls made thanks to the incentives SetSail put in place. But increased activity wasn’t the point. Instead, SetSail encouraged their reps to focus on specific behaviors — such as multi-threading and engaging with senior contacts — that led to an increase in closed-won dollars per rep of over 12%. If they could do that for an enterprise like Dropbox, they could do it anywhere.

Current market conditions have SetSail perfectly positioned

The workforce was already transforming; then COVID-19 hit. We all went remote, the economy collapsed, and tech startups were laying off employees left and right. But SetSail with its “micro-incentives” approach is positioned to weather the storm.

With sales targets, quotas, and roles changing at virtually every organization, what to do with incentive compensation has become even more pressing. For instance, where core sales compensation plans typically focus on closing the deal, during COVID-19 and its increased focus on redirecting sales teams to spend time on customer retention, relationship building, and customer engagement at virtual events, companies were able to incentivize those behaviors and keep their reps motivated. They’ve continued to build better sales habits, while other sales orgs have floundered. This is one reason why during the quarantine and economic downturn, SetSail has continued to close new logos and grow the team.

Why Operator Collective invested

It was no one thing that pushed us to invest. Yes, it was our experience at Salesforce, SaaStr, and beyond that helped us understand the problem SetSail is solving. Yes, it was their Google experience and success with Dropbox. And yes, it’s been their continued success despite a global pandemic. We believe in the founders and their team. It’s truly the confluence of many factors that has us believing in the long-term success of SetSail.

We’re excited to see what the future holds for them. But don’t just take our word for it. Check out SetSail for yourself right here.

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