Limelight Health

Jason Andrew spent 22 years in the insurance industry before co-founding Limelight Health in 2014 with three partners. The company started as a multi-carrier quoting system for insurance brokers—a straightforward software solution to a pain point he knew intimately. In year one, they built a prototype using a single programming language and leveraged co-founder Michael's deep industry relationships to land their first customers. "We had about 20 to 30 clients that paid us about $1000 total in advance," Jason recalls. "They really did it based on the fact that we had a prototype that they believed we would deliver to them. It was on the relationships and the trust."

Just a year in, everything changed. Another relationship—an angel investor introduced by Michael—connected the company to one of the world's largest insurance carriers. The carrier wanted the product. Jason faced a critical decision: stay small in the broker channel or bet big on enterprise. With only 13 employees, he chose the latter. "We had to take our baby, which we just built, put it out on the doorstep in the rain, ignore it and go all in on this insurance carrier, which is gonna pay us about a million dollars in revenue for the next year of work." For two years, they rebuilt the product for the carrier while keeping broker customers alive with minimal resources. By 2018, they had two parallel businesses: 400 broker customers and five carrier customers.

Competing against entrenched players (most had been in the market 27 years and raised ~$100M vs. their $10M) required more than product excellence. Jason and co-founder Garrett Viggers, a musician, infused the company with authentic culture. They played music during late-night engineering pushes, eventually making it a company tradition. As the team grew, they serenaded customers on site, held company concerts during COVID, and became known for a quirky human touch. "We probably spent as much time thinking about culture and doing quirky stuff like that as we did building the company," Jason says. The strategy worked: customers dropped their guards, the sales team built deeper relationships, and the acquiring company later adopted the practice, sponsoring the largest SureTech event globally.

By late 2018, after raising a Series C of $30 million, Jason brought in a seasoned product leader who pushed hard focus. The company made the painful decision to cut the 400-broker customers entirely and concentrate exclusively on the five-carrier market. "We cut off completely the broker channel, which was really scary and got rid of 400 customers." This focus unlocked inbound interest from four large carriers they'd cultivated relationships with over years. However, Jason assessed the competitive landscape—immature product, massive capital needs, rapidly consolidating market—and concluded the path to scale would be protracted and risky. In 2020, after eight months of acquisition conversations, Limelight Health was acquired for a $93 million exit, with Jason having raised $44 million over four rounds. Revenue had grown from $1,000 to nearly $19 million, with a 50/50 split between SaaS ARR and services revenue from enterprise deployments.

Jason credits relationships at every stage—from customers to advisors to hires. He cold-called Pete Espinoza, former head of sales at Guidewire, who not only advised but brought his entire enterprise sales team into Limelight. A fifth employee from Guidewire joined the board. These relationships gave tactical roadmaps and credibility. Equally important: knowing when to tap out. "We had a very immature product" and competitors far ahead. The decision to exit proved "a really good tap out."