Setsail Raises $26M Series A to Revolutionize Sales Compensation

SetSail is aiming to revolutionize sales compensation by distributing payments throughout the sales process, instead of relying on a single commission payment after a deal is finalized. The company recently announced a $26 million Series A funding round.

Insight Partners spearheaded the investment, with contributions from existing investors Wing Venture Capital, Team8, and Operator Collective. This latest investment increases the total funding secured by the company to $37 million, as stated by SetSail.

SetSail integrates with your CRM, email, calendar, and other relevant systems to gather data regarding the advancement of each sales opportunity. It then employs machine learning to identify key points within the sales cycle where rewarding the salesperson for their progress would be appropriate.

As CEO and co-founder Haggai Levi shared during the startup’s $7 million seed round announcement in July, the traditional single commission structure can discourage calculated risk-taking.

Levi explained that the concept of reimagining compensation plans resonated strongly with sales leaders during the pandemic, particularly as roles evolved and teams became geographically dispersed due to COVID-19. However, he emphasized that while rethinking compensation was a significant driver, SetSail’s ability to connect to various sales systems to facilitate these new payment approaches was equally crucial.

“I believe it extends beyond just compensation itself. It’s also about connecting to all your data through an all-encompassing platform that provides insights into interactions between you, your sales team, and your customers, and then leveraging behavioral science and machine learning to inform compensation strategies,” he clarified.

The company started 2020 with a base of five customers, a typical beginning for a young startup, but concluded the year with over 20 clients, including prominent names like Cisco, Dropbox, and HubSpot. Currently, the platform is utilized by more than 5000 sales representatives.

Despite the expanding user base, Levi affirmed that the company has no intention of aggregating customer data, ensuring that each client’s information remains separate to facilitate the creation of tailored compensation plans. “We avoid acting as a data aggregator to guarantee that every customer’s data is encrypted and stored in a distinct, secure environment. We believe the potential benefits of cross-customer knowledge are outweighed by the risks associated with data privacy,” he stated.

SetSail currently employs 35 individuals, with five additional hires scheduled to begin work in the coming weeks, and intends to grow its team to 70 by year-end. The company is actively focused on building a diverse workforce. As a starting point, Levi noted that the company’s board includes two female members. He acknowledged that hiring, in general, presents challenges for CEOs, especially in the early stages, and building a diverse team is even more demanding, but he stressed the importance of prioritizing diversity from the outset, as neglecting it limits access to half of the available talent pool.

Looking ahead, Levi anticipates maintaining some level of in-person office presence once the pandemic subsides, despite the team being distributed across San Francisco, New York, and Tel Aviv. He expects to adopt a hybrid work model, requiring less office space than might have been necessary before COVID-19.