A Workers’ Comp Tech Strategy With A Bootstrapped Mindset 

By James Benham, Co-Founder, CEO, JBK, and author of Be Your Own VC 

If you lead a workers’ comp program today, you don’t need one more vendor pitch to know the landscape is changing. You’re hearing about AI intake, automated medical summaries, predictive triage, and new dashboards almost every week. At the same time, your claims teams are handling more complexity per claim, aging workers, co-morbidities, psychosocial factors, even as lost-time frequency continues its long downward trend. NCCI’s 2024 State of the Line guide notes that lost-time claim frequency for Accident Year 2023 is estimated to be 8% lower than 2022, more than double the long-term average annual decline of 3.4%. 

The 2024 Workers’ Compensation Benchmarking Study from Rising Medical Solutions, summarized in Risk & Insurance, talks about claims organizations “balancing digital transformation with human-centered claims management” and shows top payers using AI and analytics to amplify adjusters rather than replace them.  That’s encouraging, but behind the buzz is a quieter reality: every new tool, pilot, and integration comes out of the same finite pool of resources you use to support injured workers and the people who serve them. 

Whether you use the phrase or not, you’re already your own venture capitalist (VC). You are effectively funding innovation from within your own results. In my book, Be Your Own VC, I outline bootstrapping principles that helped my team develop insurance technology for over two decades without outside investors. Those same principles can help workers’ comp leaders decide which vendors and tech partners deserve a place in their programs, and which should stay on the conference floor. Here are a few that I believe to be the most relevant: 

Principle 1: Cash is King 

When I say “cash is king” in the bootstrapping world, I’m not talking about piling up money for its own sake. I’m talking about keeping enough oxygen in the system so the business can keep serving customers, keep paying people, and keep its promises when the economy zigzags. That mindset translates directly into workers’ comp. 

Over the past few years, workers' compensation has been described as a financially strong system, with steady reserve positions and a declining claim frequency. NCCI’s State of the Line materials highlight that lost-time claim frequency has fallen 8% year-over-year, with medical and indemnity severities seeing moderate increases of around 2% and 5%, respectively.  Fewer claims doesn’t mean less work; it means each remaining claim is, on average, more complex and more important to get right, clinically, legally, and humanly. 

That’s the moment when every dollar you move into “innovation” needs to be accounted for. A seventh claims system or another AI pilot doesn’t just sit on a shelf; it displaces something else you could have used to support adjusters, nurses, physicians, or injured workers. 

A bootstrapped mindset doesn’t say “don’t spend.” It says: if you’re going to fund a new partner or tool, insist on a plain-language story about where that spend improves life for injured workers and the people who serve them. Does this shorten the time to first contact? Does it help you identify the proper care earlier for a complex injury? Does it free adjusters from low-value tasks so they can spend more time on conversations that change outcomes? 

There is real potential in the tools on offer. In the latest Workers’ Comp Industry Insights Survey from Healthesystems and Risk & Insurance, more than 60% of respondents say advanced technologies like analytics, machine learning, and AI are gaining prominence as ways to address their top challenges. A separate data snapshot from Zipdo suggests that AI in workers’ comp has reduced claims processing time by about 40% and cut adjusters’ administrative burden by roughly 35% where it’s implemented well. 

The question is whether a specific partner, in your specific program, can earn its place by clearly supporting better outcomes. 

Principle 2: Build what you have to so you can build what you want to 

I learned to code in a Texas A&M dorm room, but my first real business wins didn’t come from software products. They came from services, helping people get online, configuring systems, solving practical problems for paying clients. Those cash-flowing services funded the products my team really wanted to build later. In the book, I describe this as “build what you have to so you can build what you want to.” It became one of the pillars of how we ran JBK and launched tools for construction and insurance. 

Workers’ comp leaders can use the same lens when considering technology. You don’t have to build everything yourself. In fact, trying to build everything internally is one of the fastest ways to overload your teams and stall change. Instead, you can treat your internal capacity, your limited pool of analysts, IT time, clinical experts, and frontline leaders, as the scarcest capital you have. 

There are capabilities where it makes sense to lean on vendor partners: document ingestion, basic medical record summarization, standard workflow routing, communication infrastructure, or tools that handle common patterns across many lines of business. Articles like “How AI Is Changing the Claims Landscape” in Risk & Insurance and Aon’s “How Artificial Intelligence Is Changing Workers’ Compensation” both describe how AI is already supporting claim triage, identifying nurse‐case‐management needs earlier, and taking manual friction out of routine tasks so people can focus on higher-value decisions. 

Where you may want to “build what you want to” is in the places that express your philosophy of claim management. That might include: 

• How do you sort claims by how risky and complex they are? 
   

• How do you define and measure the moments that matter in a claim’s life? 
   

• How do you weave together clinical, psychosocial, and return-to-work supports? 
   

For those elements, you may still rely on a vendor’s plumbing, but the design and logic are yours. A good tech partner will understand that distinction and help you protect it. They’ll bring you a stable platform for what’s common, then collaborate with you to encode what’s unique about your program without forcing you into a one-size-fits-all template. 

In a bootstrapped environment, it’s survival. Spend all your internal “build” capacity replicating what the market already provides. You’ll have nothing left to invest in what differentiates your program for injured workers, employers, and brokers. 

Principle 3: Choose your partners carefully 

One of the more personal chapters in Be Your Own VC is about partners. In my world, that has meant co-founders, vendors, early employees who sat in yellow plastic chairs with me in our first Argentina office, and a small circle of advisors and clients who stayed through good times and bad. I’ve seen what happens when those relationships are strong and aligned, and I’ve seen what happens when they’re not. 

When you run a workers’ comp program, your long-term vendors are, in practice, partners. They may not sit on your cap table, but they influence your workflows, your data, and the day-to-day experience of injured workers and adjusters for years. You shouldn’t choose them quickly. 

The Workers’ Compensation Research Institute (WCRI) recently published “Artificial Intelligence in Workers’ Compensation: An Overview of Promises and Challenges,” based on interviews with leaders from insurers, employers, providers, worker advocates, and regulators. One theme in that report is that AI’s value depends heavily on governance and alignment: how it’s implemented, how transparent it is, and how well it supports, not undermines, the mission of helping injured workers recover and return to work. 

This report shows that finding the right partner is a test of partnership. A strong vendor partner in workers’ comp looks less like a faceless software company and more like an extension of your team. They spend time understanding your jurisdictional footprint and how your people actually work. They are honest about where their tools are proven and where they are still learning. They participate actively in training and adoption, not just configuration. They accept being measured on things you care about, such as time to first meaningful contact, reduced administrative load per claim, better visibility into complex cases, or smoother return-to-work pathways, rather than just logins and usage charts. 

The newly released Workers’ Compensation Benchmarking Study report from Rising Medical Solutions underscores how leading claims organizations are trying to “balance digital transformation with human-centered claims management.” That is exactly where the right partner makes or breaks you: do they help your adjusters, nurses, case managers, and providers become more capable and more connected to injured workers, or do they treat them as obstacles on the way to a fully automated vision? 

When you are your own VC, you don’t have the luxury of partners who look good in a launch webinar but disappear during the hard months of integration, policy interpretation, and refinement. You need teams who will answer the phone when an adjuster in a tough jurisdiction says, “This isn’t working the way we need it to,” and who will treat that feedback as design input, not a nuisance. 

Be Your Own VC in Workers’ Comp 

If you strip away the jargon, being your own VC in workers’ comp is pretty simple. You recognize that your resources are finite. You acknowledge that every initiative you fund is a choice about how you want to show up for injured workers and the people who serve them. And you apply a few clear principles before you sign anything. 

First, you steward cash like it’s oxygen. You don’t chase technology for its own sake. You ask how a partner or tool will concretely support better conversations, better decisions, and better journeys through injury and recovery. 

Second, you build what you have to and save energy for what you really want to shape. You let vendors handle the generic plumbing, but you stay deeply involved in the parts of the system that reflect your values and your strategy for care. 

Third, you choose partners slowly and intentionally. You look past the pitch deck and ask: Will these people stand in the hard places with us, through regulatory nuance, culture change, and the unglamorous work of implementation? 

The workers’ comp industry is already experimenting with AI, automation, and new tools at a rapid pace. The differentiator won’t be who bought something first. It will be who funded the right things, with the right partners, for the right reasons. 

You don’t need to become a startup to think like a bootstrapped founder. You just need to remember that the resources you’re spending are your own, and that the real return you’re aiming for is a system that can continue to support injured workers year after year, no matter how the tools change. 

James Benham 

James Benham is the Co-Founder and CEO of JBK, a technology and consulting firm serving the insurance and risk management industry. He also hosts The InsurTech Geek podcast and is a frequent speaker on insurance innovation. 

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