SetSail nabs $26M Series A to rethink sales compensation


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SetSail wants to upend the way sales people get compensated by paying them throughout the sales cycle, rather than a single commission after the sale closes. Today, the startup announced a $26 million Series A.

Insight Partners led the round with participation from existing investors Wing Venture Capital, Team8 and Operator Collective. Today’s investment brings the total raised to $37 million, according to the company.

SetSail connects to your CRM, email, calendar and other systems that have signals about the progress of a particular sale, and then using machine learning looks at points in the sales cycle where it would make sense to reward the sales person for the progress they are making.

As CEO and co-founder Haggai Levi told me at the time of the startup’s $7 million seed round in July, the single commission system discourages risk taking:

“If I’m closing the deal, I’m getting my commission. If I’m not closing the deal, I’m getting nothing. That means from a behavioral point of view, I would take the shortest path to win a deal, and I would take the minimum risk possible. So if there’s a competitive situation I will try to avoid that,” he said in July.

He said the idea of changing the way we think about compensation resonated with sales executives during the pandemic, especially as everyone’s role got altered and teams became distributed because of COVID, but he says while rethinking compensation was certainly a big factor so was SetSail’s ability to connect to all of the sales systems to help build these new approaches to pay.

“I think it’s even beyond just compensation. […] It’s also connecting to all of your data using an end-to-end platform that helps you understand what’s happening between you, your reps and your customers and allowing you to tie that back in using behavioral science to machine learning-based compensation,” he explained.

The company began 2020 with five customers, a reasonable start for an early stage startup, but it ended the year with more than 20 including Cisco, Dropbox and HubSpot. It now has over 5000 sales reps using the platform.

In spite of the growing number of users, Levi says they have no plans to aggregate data, leaving each customer’s data as distinct to build the compensation packages that make sense to them. “We try not to play kind of the data, aggregator role because we want to make sure that every customer’s data is encrypted and secured in a completely different container. The trade off between getting knowledge between customers versus receiving their data is is too high in our opinion,” he said.

The company now has 35 employees with five more hired who will be starting in the next several weeks and plans to reach 70 by the end of the year. They are thinking hard about how to hire a diverse workforce. For starters, Levi says that the company board has two female members. He says hiring in general is a challenge for every CEO, especially early on, and hiring a diverse group even more so, but he says it’s important to be thinking about this from the start because from a gender perspective at least, you are losing half the talent pool if you ignore it.

When the pandemic is over, he sees having at least some in-person office presence in spite of being spread out across San Francisco, New York and Tel Aviv, but it will be probably be a hybrid approach and not require as much office space as they might have rented prior to COVID.


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