Healthcare payments consume between $650 billion and $1 trillion annually in billing and insurance-related costs—an amount comparable to the entire U.S. Defense Department budget. At the heart of this staggering inefficiency lies a fundamental problem: when patients receive care, nobody actually knows in real-time whether the insurance will pay for it. Mike Desjadon, CEO of Anomaly, spent nearly two decades in healthcare payments before building a company to solve this core issue. In this episode, we explore how Anomaly is creating "payment assurance" for h...
Healthcare payments consume between $650 billion and $1 trillion annually in billing and insurance-related costs—an amount comparable to the entire U.S. Defense Department budget. At the heart of this staggering inefficiency lies a fundamental problem: when patients receive care, nobody actually knows in real-time whether the insurance will pay for it. Mike Desjadon, CEO of Anomaly, spent nearly two decades in healthcare payments before building a company to solve this core issue. In this episode, we explore how Anomaly is creating "payment assurance" for healthcare—bringing the same real-time payment certainty that exists everywhere else in commerce to an industry desperately in need of it.
Topics Discussed:
- The massive scale of healthcare billing costs and why precision is impossible at this scale
- How the complex coding system (ICD, CPT, revenue codes) creates a "ridiculous Rubik's Cube" of payment determination
- Why healthcare lacks payment assurance while every other industry has real-time payment certainty
- The fundamental information asymmetry between providers and insurers that drives administrative waste
- Anomaly's approach to using AI and machine learning to predict payment outcomes early in the care process
- The strategic decision to focus exclusively on providers rather than serving both sides of the market
GTM Lessons For B2B Founders:
- Avoid "Annual Curiosity Revenue" in favor of deep customer relationships: Mike warns against chasing what he calls "ACR" - contracts driven by curiosity about new technology rather than real value. Instead of racing to accumulate surface-level customers, Anomaly focuses on 1-5 anchor customers where they forward-deploy engineers and dedicate leadership attention. As Mike explained, "I'd rather take a much smaller amount of those trusted pitches... find me 10 of the right conversations, don't find me a hundred surface level conversations." In healthcare's 14-month sales cycles, shallow relationships burn runway without building sustainable growth.
- Match your go-to-market strategy to industry realities, not investor expectations: Healthcare's long sales cycles and conservative nature require a fundamentally different approach than traditional SaaS growth models. Mike structured Anomaly's capital and hiring strategy around 14-month sales cycles rather than trying to compress them. "If you know that it's a 14 month sales cycle... being realistic about those timeframes and those capital structures, you just make sure your plan on burn matches your plan on strategy." This meant hiring customer success and engineering talent before traditional sales roles, aligning team composition with the actual customer adoption process.
- Segment ruthlessly based on transformation readiness: Not every healthcare organization is ready for transformative technology. Mike emphasizes the critical need to identify whether prospects are "looking for transformation" versus "looking to automate an isolated process." He shares that distinguishing between these segments determines the entire sales approach. Organizations seeking transformation are willing to work through implementation complexity for substantial outcomes, while those seeking automation want predictable, incremental improvements. Misreading this distinction leads to failed sales cycles and misaligned product development.
- Use forward-deployed engineering as a competitive advantage: Rather than traditional customer success managers, Anomaly deploys engineers directly to customers during implementation. This approach proves particularly valuable in AI/ML applications where the technology is rapidly evolving and customer needs aren't fully defined. Mike notes, "Having engineers in that has been hugely valuable for us because we're able to really quickly deliver value, very quickly deliver outsized value." This strategy enables rapid iteration, builds deeper technical trust, and often leads to expanded contracts through demonstrated capability rather than traditional sales pitches.
- Build category credibility through case studies, not connections: In healthcare, having impressive investors or warm introductions matters far less than demonstrating proven results with known organizations. Mike emphasizes, "What you need in healthcare is slapping six case studies down the desk... show me the six organizations that I know that you work with that are going to tell me I should work with you." This insight drives Anomaly's entire early-stage strategy—prioritizing customer success and measurable outcomes over rapid customer acquisition, building the credibility foundation needed for future sales acceleration.
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