Calvin Gilman is an Insurance Advisor at Advance Insurance Agency in Minneapolis, where he advises SMBs and nonprofits on commercial coverage and risk strategy. Before entering insurance in 2016, Calvin spent nearly a decade in digital media and gaming — Electronic Arts, CBS Interactive, Playwire — which gives him a different lens on how technology intersects with risk. He and Vivek first met at gener8tor, a Midwest startup accelerator, in 2019. Calvin has provided insurance coverage for the company since its Qlicket days, stayed in touch through the pandemic, and now advises Teamforce AI on both its own coverage needs and the broader insurtech landscape. In this episode, Vivek walks Calvin through what Teamforce does and asks him to react — not as a supporter, but as a broker who has to justify every dollar his clients spend.
The Question Nobody Wants to Ask Out Loud
Every early-stage company tells itself a story about product-market fit. The pitch deck says the problem is real. The early data says the solution works. The advisors nod. But at some point, you need someone from the industry you are selling into to sit across from you and say whether any of this actually matters to the people writing checks.
Calvin is that person. He is not an investor. He is not a co-founder. He is a broker who spends his days helping businesses navigate insurance contracts that run hundreds of pages, distilling what matters and what does not. His job is to retain clients by lowering what they pay and improving what they get. If a tool does not help him do that, he has no reason to recommend it.
So the question on this episode was simple: does what Teamforce is building matter to the people you serve? And Calvin’s answer was honest. Yes — but not yet in the way we need it to.
The Case Study Barrier
Calvin’s clearest piece of feedback was also the most uncomfortable. The concept of using leading indicators — frontline signals captured before incidents occur — to reduce workers’ comp claims makes intuitive sense. But intuitive sense is not what gets a broker to bring a vendor into a renewal meeting.
What gets a vendor into that meeting is proof. Specifically, examples of current success as the best predictor of future success. Calvin made the point that preventative tools face a structural challenge: it is difficult to prove that something did not happen because you caught it. The attribution problem is real. When a company deploys Teamforce alongside twenty other safety practices, isolating the impact of any single tool requires a level of rigor that most early deployments do not yet have at scale.
This is the tension Teamforce lives in right now. The initial proof points are compelling — signals captured that no other channel surfaced, verified fixes with documented avoided cost. But the volume of case studies needs to grow before brokers and carriers treat it as a standard recommendation rather than an interesting experiment.
Why the Companies in the Most Pain Are Not the Right Customers
Calvin reframed something we had been thinking about for months. Early on, Teamforce targeted companies with recent OSHA activity or elevated experience modification rates, on the theory that pain creates urgency. Calvin pushed back on that logic.
Companies in financial distress from high claims are already under downward pressure. Asking them to invest in a new tool while their workers’ comp costs are 80 percent higher than two years ago is asking them to spend more money at the worst possible moment. They may recognize the problem, but they are in crisis mode, not buying mode.
The better target, Calvin argued, is the company that sees what is happening to its peers and has the means and the mindset to act before it happens to them. These are companies that attend industry conferences, hear that 30% of their peers are dealing with elevated claims, and are self-aware enough to know they are not immune — they have just been lucky. They have the budget to be proactive. And they are culturally ready to implement something that requires trust between the workforce and management.
This maps directly to why captives are emerging as the highest-leverage channel for Teamforce. Captive insurance members pool risk, hold one another accountable, and tend to be more proactive by nature. They are not waiting for the crisis. They are trying to avoid it.
How Brokers and Carriers Actually View Outside Tools
This was the segment that revealed the most about how the market works. Calvin explained what happens when a brokerage walks into a renewal meeting with a mid-market manufacturer. They bring a team. If workers’ comp is a pain point, they bring years of claims data, experience modification history, and often the carrier itself. Carriers like Travelers and Hartford are Fortune 500 companies with their own internal tools, and they want to retain business by providing bespoke solutions — not by recommending outside vendors.
The dynamic gets sharper with AI. Carriers believe they can build comparable tools in-house, which makes them more reluctant to engage with outside technology. Whether or not they actually can is a separate question, but the perception creates friction.
Where the opening exists is on the broker side. Brokers are not building tools. Their job is to retain clients, and they do that by lowering what clients pay and bringing solutions that reduce risk. If Teamforce can demonstrate that deploying its platform leads to lower claims frequency, better experience mods, and ultimately lower premiums, brokers have every reason to recommend it. The tool becomes part of their value proposition to the client, not a competitor to it.
Calvin put it simply: agents care about the bottom line. If there are tools that help them achieve that goal, they will use them because they want to retain the business.
Fraud Is Not What the CFO Thinks It Is
A CFO Vivek had spoken with months earlier said his first priority was tackling workers’ comp fraud before considering any preventative technology. Calvin’s response reframed the entire issue.
Fraud exists. But what most people call fraud is not criminal intent. It is a spectrum. On one end, there is the employee who genuinely does not want to return to a workplace that injured them, where nothing has changed, where they feel pressure to meet production goals but no corresponding investment in their safety. On the other end, there is the employee dealing with financial pressure who stays out longer than necessary because the incentive structure makes it rational to do so.
Calvin’s point was that fraud correlates more with company culture and economic conditions than with individual character. When the economy worsens, fraud increases — not because people become worse, but because financial pressures change the calculus. And the instinct to point the finger at employees is often easier than asking what the company could do differently to change the incentive structure.
This connects directly to the cultural readiness argument. The companies that treat fraud as a workforce problem rather than a systems problem are the same companies that are not ready for a tool like Teamforce. The ones that ask what they can do to create an environment where people want to come back to work, where they feel safe and heard — those are the companies where leading indicator tools actually land.
Is This Inevitable?
Calvin said yes. He drew the comparison to nurse hotlines, which did not always exist in the workers’ comp space but are now widely adopted and feel native to the industry. The same is true for modified duty programs that put injured workers into alternative roles to reduce time away from work. These tools were once novel. Now they are standard.
His argument was that any tool that demonstrably reduces claims cost will eventually become standard. The path from novel to standard runs through proof — enough case studies, enough data, enough brokers and carriers seeing the results in their own clients’ numbers. The question is not whether leading indicator tools will become part of the workers’ comp infrastructure. The question is how long it takes and who wins the market.
The Liability Question Nobody Has Answered Yet
The conversation closed on a topic that sits just over the horizon. As humanoid robots enter factories and autonomous vehicles enter fleets, the liability landscape is about to get significantly more complex. If a humanoid robot injures a worker, who is responsible? The manufacturer of the robot? The company that deployed it? The software provider?
Calvin drew a parallel to the early internet. The Communications Decency Act removed liability from internet companies to encourage industry growth. That worked for economic expansion, but it also created the conditions for the data privacy and platform accountability problems the industry is grappling with now. His concern is that a similar dynamic could play out with autonomous machines — liability protections that enable growth in the short term but create compounding risk management challenges downstream.
For manufacturers deploying these technologies, the implication is that risk management infrastructure needs to get ahead of deployment, not follow it. The tools and frameworks for managing human-machine interaction risk on the plant floor do not fully exist yet. That is a problem for carriers, for brokers, and for the companies that will be navigating incident liability in real time.
Watch the Full Episode
Calvin Gilman brings the perspective Teamforce rarely gets on camera: the broker who has to justify every recommendation to clients operating on thin margins. His feedback on what works, what is missing, and where the opportunity sits is the kind of honest assessment that shapes how we go to market.
Connect with Calvin Gilman on LinkedIn.