Insight Squared

Fred Shohmer founded Insight Squared in January 2011 with two co-founders to solve a problem embedded in the sales operations world: Salesforce was missing critical reporting and analytics features that teams needed for forecasting, pipeline management, rep coaching, and board preparation. Rather than compete broadly in the crowded business intelligence space, Shohmer made a deliberate strategic choice to pick sales as their "major" and become subject matter experts in that vertical—a rare positioning at the time.

Unlike many bootstrap founders, Shohmer raised venture capital from day one, securing $1M in seed funding from Boston-based investors. This decision reflected both the team's ambitions and personal constraints: the co-founders had families to feed and substantial career opportunities they were leaving behind. "We wanted to get off to a running start and build a team," Shohmer explained. The capital allowed them to make significant R&D investments in the early years that would have been impossible under a bootstrap model. Over time, they raised $27M total in venture capital.

Insight Squared started with SMB customers—companies with 25-200 employees using Salesforce—but as the product matured, they moved upstream into mid-market and enterprise. By the time of this interview, they had surpassed 750 customers, including publicly traded companies and well-known brands like Gainsight and Pendo. Their positioning in the emerging "sales technology" category proved prescient: while analytics was crowded, sales analytics was wide open. Shohmer observed that sales was experiencing a similar digital transformation that marketing had undergone a decade earlier, creating massive opportunity for specialized tools.

In 2015, Insight Squared doubled headcount following a funding round and moved into a larger space. However, this aggressive growth backfired—the company "got a little bit over our skis" in Shohmer's words, requiring layoffs about a year and a half to two years before this interview. Shohmer took full responsibility as CEO and emphasized that despite the difficult decisions, his core value remained: making Insight Squared "the best place any of our team has ever worked." The company won best place to work awards every year since founding, even as they managed the painful restructuring.

After the reset, Shohmer shifted focus toward sustainable growth and profitability. Rather than chase aggressive scaling, the company focused on product maturity—working with larger organizations as the platform's power increased. Revenue grew substantially relative to headcount: despite only a slight increase in team size post-correction, their customer base and revenue expanded significantly. Shohmer credited this to the maturation of their product and ability to serve larger organizations.

With 135 people concentrated in Boston (and a few remote team members), Insight Squared operates in a market Shohmer sees as still early. Sales technology was fragmented—five years prior, a CEO wouldn't even understand the concept of a "sales tech stack." Now, companies like Insight Squared worked alongside multiple specialized tools (Clearbit, FullContact, Amaze, Chorus, and others) to drive account-based selling and machine learning-driven coaching. Shohmer refused to share exact ARR figures but indicated they had substantial revenue. Looking forward, he positioned sales enablement as the next frontier of enterprise software, roughly where marketing tech was a decade prior—a massive opportunity for focused, specialized players who mastered a single domain.