Randall’s philosophy may sound a bit too good to be true – until, that is, you see his resume.

In addition to working as a retirement and group health consultant and analyst for companies like Milliman, Northern Trust and Washington Mutual, he was hired as a benefits manager by Safeway in 2009. In 2011, Tesla Motors tapped Randall as its senior manager of global benefits.

He left Tesla last year. The company went public in 2010, and its stock appreciated roughly 900 percent during Randall’s tenure, which in part explains his flexible and philosophical approach to running Ursa Major.

Along with personal financial freedom, Randall says, he left Tesla with two other things: a vision of how workplace benefits could be designed to address employers’ cost concerns and workers’ benefits needs; and a healthy dose of reality when it comes to the regulatory and market barriers subjecting today’s benefits market to, as Randall calls it, antiquated “19^th century thinking.”

“Every aspect of Tesla’s culture is designed to generate innovation, motivate forward thinkers, and question the status quo,” says Randall, who was one of 900 total employees when he joined the automaker; today, Tesla employs more than 14,000 workers.

That ethos eventually filtered down to the company’s human resource department, he explained.

“The engineers at the company were asked to reimagine the most basic, established concepts,” Randall said. “It didn’t make sense to roll out a benefits package that looked the same to all of these workers that were pushing to innovate on their end.”

Keeping up with that culture was a challenge -- and ultimately instructive to the company’s human resources specialist.

“Engineers are logical people,” said Randall. “They would come to us with benefit questions and ask about options that were really sensible — in one case, an employee wanted benefit dollars to buy a bike. That’s a really creative idea that has upsides for employers’ overall wellness initiatives.”

Randall’s biggest frustration, though, was that such logical, sensible thinking was impossible to apply to even the most innovative benefits design.

“As creative as you want to be, regulations limit you,” he said. “Much of the thinking in the benefits world is really, really old.”

As a compromise, Tesla freed up as much money as possible, allowing employees to spend the benefits dollars however they saw fit, within regulatory parameters and constraints designed by the company’s HR team.

“We wanted to offer benefits our employees wanted, so we set out to understand every option available, and determine how much of their benefit dollars we could free up,” Randall said. “But there had to be guardrails, of course — employees need core protections. Every company will have a different set of guardrails and different tolerance for how aggressively they want to innovate their benefits program.”

He said that his biggest takeaways from Tesla was that company cultures are different and there is no one perfect approach to innovation for all companies.

That said, Randall added, every company’s benefits program should be a reflection of its core culture.

Technology benefiting smaller employers

At no time did Randall describe himself as a “technologist” or a “disruptor,” which is refreshing for a Silicon Valley insider who is often -- rightfully -- called both.

Like other industry insiders, he bemoans the health care market’s relative resistance to technological forces, even questioning whether it can even accurately be described as a “market.”

“It’s not a truly open market, where a consumer can walk in, see the options, see the pricing, and make decisions based on transparency,” he said.

“Choice” is instead defined by a relatively small number of major medical group providers, with Randall suggested has stifled innovation and left consumers to choose from among a narrow set of complicated options. Technology, he said, will be the key to opening and transforming today’s benefits market.

According to Randall, the technology gap is already closing -- and quickly, especially in terms of innovation with benefits administration systems.

That trend benefits smaller and midsized employers, as so-called “mega” plans remain wedded to incumbent administration systems that, in Randall’s estimation, are sluggish compared with the slick new platforms being rolled out today.

“It’s a bottom-up change,” he explained. “Small tech providers are rolling out really smart options that make employee integration simple, and they are doing it with small groups. That’s great for those employers: they can offer their employees a benefits experience superior to what you find at a giant like Apple.”

More options welcomed in the workplace

In his experience at Tesla and in other companies, where choice was built into the offerings with either non-medical and other voluntary benefits or private exchanges, Randall said most employees welcomed the changes.

“When employers add flexibility, people tend to love it,” he said. “That doesn’t mean some won’t be overwhelmed, but as a general rule people embrace choice. I never had anyone at Tesla say they were angry at us for adding more options to our plan.”

While Randall hopes his vision of extensive consumer choice of health care and benefits will someday come to be, the realist in him knows the transformation to a fully open market will be a slow one.

In the meantime, employers and employees need a genuine, non-conflicted independent voice that can put emerging benefit options into context. To that end, Randall sees a world where benefits brokers assume more of a consultative role, and less of sales role.

“In my opinion, broker-consultants that exist today should be doing that anyway.”