After years leading product across startups and scaled companies, I've spent the past several months on the other side of the table as an executive-in-residence at Cowboy. I've spent time with founders, investors, operators, and clinicians across healthcare, looking at companies tackling everything from skilled nursing admissions to operating room orchestration, new care models for autism, eating disorders, migraines, memory loss, chronic disease and more.

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A handful of interconnected themes emerged again and again. Together, they reinforce our optimism – with eyes wide open – about the opportunity for AI-powered companies to solve meaningful healthcare problems. Here are a few that stood out:

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1. The possibilities in healthcare have changed. The rules haven't.

The last wave of digital health investment produced important innovation, but it also reminded the industry how difficult healthcare can be. Many companies underestimated the complexity of clinical evidence, reimbursement, provider adoption and building sustainable business models. Those fundamentals haven't changed. What has changed is what's possible. AI is making it viable to monitor patients continuously, support clinicians in real time, personalize care at scale, and automate work that was previously too expensive or operationally complex. Combined with evolving regulation, new reimbursement pathways, and dramatically lower software development costs, founders can now tackle problems that simply weren't feasible a few years ago.

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2. Prevention is becoming a consumer line item.

Consumers are increasingly willing to pay for health information that's not easily accessed through traditional healthcare. Function Health has rapidly become one of the fastest-growing consumer health companies, giving people direct access to comprehensive testing that historically required a physician order to rule out a medical condition. Neko Health has a similar approach with preventive imaging, already completing more than 100,000 scans, building a waitlist of more than 350,000 people, and recently raising $700 million at a nearly $7 billion valuation. Consumers are no longer waiting until they become patients to engage with their health. The next challenge – and opportunity – is turning this episodic preventative testing into durable, recurring relationships.

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3. Healthcare is shifting from appointments to always-on insights.

Oura and WHOOP have brought continuous health monitoring into the mainstream. Oura, at nearly $1 billion in revenue, has evolved well beyond sleep tracking into cycle tracking, metabolic health, and glucose monitoring (through its partnership with Dexcom). WHOOP, recently valued at $10B+, has gone beyond its roots with elite athletes by adding blood biomarker analysis, strength training, and Healthspan, expanding its focus from performance optimization to long-term health. As continuous monitoring becomes more common, there's growing opportunity for specialized sensors, new diagnostic signals and software that brings together data from wearables, labs and other health signals. The next wave of innovation won't necessarily be another wearable, but products that turn this data into proactive, personalized guidance for consumers and new, actionable insights for clinicians.

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4. Specialty care is being reimagined.

New care models are expanding access to high-quality specialty care by overcoming the limitations of traditional care delivery. Midi Health, recently valued at more than $1B, helped pioneer a tech-powered approach to menopause care at scale. Equip has done the same in eating disorder treatment, caring for more than 5,000 patients, 87% of whom would traditionally have required a higher level of care, while delivering strong clinical outcomes. As demand for specialty care continues to far outpace provider supply, some of the most compelling opportunities will come from companies that rethink how high-quality specialty care can be made more accessible and effective. We're particularly excited by the innovation we're seeing across mental health, women's health, and senior care.

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5. Regulation is creating new tailwinds.

Regulation has traditionally been a barrier to innovation, but recent policy changes are expanding the range of viable business models. Expanded nurse practitioner practice authority is enabling independent practice in many states, creating new care models and business opportunities. New CMS reimbursement pathways are creating opportunities for tech-powered care models to be reimbursed, making entirely new business models economically viable. At the same time, clearer regulatory frameworks for clinical AI are accelerating adoption of applications like ambient documentation and clinical decision support. As regulation evolves, it is creating entirely new areas for innovation across care delivery, staffing, and reimbursement.

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6. Administrative workflows are finally automatable.

Healthcare has long relied on faxes, phone calls, PDFs, and manual data entry to coordinate care across providers, payers, and health systems. The combination of AI advances and new interoperability standards is making it possible to automate workflows – from prior authorization to provider credentialing and revenue cycle management – that have remained stubbornly manual for decades. Basata, one of Cowboy's portfolio companies, is using AI to automate referral management and patient intake, helping providers process referrals six times faster while increasing new patient conversions by nearly 20%. Healthcare is now setting the pace for enterprise AI adoption, with 22% of healthcare organizations using paid commercial AI applications in 2025 compared with just 9% across the broader U.S. economy.

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7. Clinician demand is reshaping enterprise sales.

With clinician burnout at an all-time high, products that meaningfully improve daily workflows are creating powerful bottom-up demand. Abridge grew from initial clinician pilots to deployments across 300+ health systems. OpenEvidence is now used by approximately 65% of U.S. physicians, reaching nearly 27M clinical consultations in a single month before expanding into enterprise-wide health system partnerships. But as the U.S. healthcare IT software market approaches $190B, clinician enthusiasm alone is not enough. The companies scaling most successfully pair strong bottom-up adoption with a clear path to enterprise purchasing from the outset, aligning their products to the economic incentives of healthcare buyers.

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8. A reimbursement strategy can't be an afterthought.

Consumer healthcare attracted unprecedented investment during the digital health boom of 2020–2021, but many of those companies ultimately struggled to build durable businesses. High customer acquisition costs, inconsistent retention, and limited pricing power made it difficult to scale on a direct-to-consumer model alone. While many hoped to expand into employer, provider, or payer channels over time, they often underestimated what it would take to make that transition. Today, founders often still start with a consumer offering because it provides the fastest path to validate demand and generate real-world data on effectiveness. But if reimbursement is part of a long-term strategy, it's as important as ever to shape the clinical evidence, product roadmap, payor and commercial strategy from the very beginning.

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We're most excited about opportunities at the intersection of these themes.

These shifts are interconnected, creating new ways to solve some of healthcare's most challenging problems. We believe the most promising companies will emerge at these intersections, while also fitting naturally into how healthcare is delivered and paid for.

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Perhaps my biggest takeaway from the past months is just how much I love building products that improve people's lives, and there's never been a better time to build in healthcare. As I wrap up my time as an EIR, I'm excited to stay close to the Cowboy team as a Wrangler while rolling up my sleeves again.

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If you're working on something ambitious in healthcare, we'd love to connect. You can reach the Cowboys at hello@cowboy.vc and me personally at donna@donnaboyer.com.