How to Sell SaaS in a Slow-Moving, Regulated Industry | Allen Cooper | 369

In this episode of SaaS Fuel, host Jeff Mains sits down with Allen Cooper, co-founder and CEO of Ready List, to unpack what it really takes to build and scale SaaS companies in healthcare—one of the slowest, most regulated industries on the planet.

The conversation dives deep into navigating 12-18 month enterprise sales cycles, recovering from product failures, hiring salespeople with domain credibility, and building remote culture that sticks. Allen candidly discusses which products flopped (and why early validation matters), how piloting with hospitals builds irreplaceable trust, and where healthcare technology is headed as AI and automation remove low-value tasks from clinicians.

If you're building SaaS in a complex, regulated space—or considering it—this episode offers grounded, real-world insights on winning where speed isn't optional, but patience is mandatory.

Key Takeaways

[5:45] - From Investor to Operator: Allen explains how he transitioned from working capital partner to healthcare entrepreneur, finding the intersection between business interest and solving real transparency problems in healthcare quality metrics.

[7:05] - The Transparency Gap: Healthcare's biggest early pain point was lack of transparency and the over-utilization problem driven by low-deductible plans that conditioned patients to overuse the system.

[9:39] - The Ready List Origin Story: Ready List was born from a partnership with a West Coast hospital opening with a mission to eliminate paper—specifically targeting environmental services teams still relying on paper-based cleaning protocols.

[10:57] - BR90 & Birth Registration: How a gap in the birth registration process led to building VR90, which reduced what used to take hospitals 15-20 minutes per birth down to 15-20 seconds using robotics process automation (RPA).

[16:43] - Products That Flopped: Allen admits early products failed because they relied on someone's opinion and story without proper market validation—a costly lesson in distinguishing wants from true needs.

[17:02] - The Pilot-First Approach: The critical shift to piloting products with early adopters before full investment, ensuring real validation and ironing out issues with actual users rather than guessing.

[20:50] - Timing & Government Risk: Why timing matters enormously in regulated industries, where a single law or government decision can make or break your product overnight.

[22:33] - Navigating Long Sales Cycles: Healthcare sales cycles run 12-18 months, complicated by varied fiscal years across hospitals. Allen shares how understanding budget cycles and offering no-cost pilots can compress timelines.

[25:16] - The Trust Equation: Piloting builds trust exponentially faster than cold outreach. When hospitals experience both your product and your support, they become far more tolerant when issues arise.

[28:34] - Sales Hiring Evolution: Allen's shift from hiring SaaS-savvy generalists to requiring healthcare domain expertise—seasoned salespeople who already have relationships and understand the ecosystem.

[34:18] - Building Remote Culture: How Ancilla moved from full in-office to hybrid, discovering that quarterly in-person gatherings plus weekly virtual team socials (online games, baking sessions) build the trust needed for remote teams to thrive.

[39:38] - Advice for Complex Industries: Time is both friend and enemy—don't give up prematurely on Blue Ocean products, but also don't drag on what isn't working. Always validate that you're solving a need, not a want.

[42:05] - The Future of Healthcare Tech: Allen predicts increased adoption of robots and AI to handle low-value tasks (documentation, routine activities), freeing providers to focus on direct patient care where they add the most value.

Tweetable Quotes"A want is hard to sell. It's gotta be something that's needed—if you take it away from them, you're gonna be giving back a pain point." - Allen Cooper"Don't rely on someone's opinion and idea and hope that it works. Partner up, pilot it, validate it—especially if you're not an industry person." - Allen Cooper"Getting a sales individual that is in the network really goes a long way with that trust. Being in that space is the lens that I have now." - Allen Cooper"When you just get bombarded by vendors you don't know, you're just like 'I don't want it'—I'm trying to find a way to navigate through that to build trust." - Allen Cooper"Time heals anything you think you can't get out of. Don't drag your feet, but don't get discouraged when things aren't working today, this week, or this month." - Allen Cooper"A need is resilient to any downturn of a market because a need will be needed regardless of what happens. Always serve a need, not a want." - Allen CooperSaaS Leadership Lessons1. Validate Relentlessly Before You Build

Allen's biggest failures came from building products based on someone's opinion and compelling story without market validation. The lesson: Don't invest heavily until you've piloted with real users. Early adopters will tell you if you're solving a real problem or chasing a phantom need. Partner with 2-3 hospitals (or relevant organizations in your industry) to validate assumptions before going all-in.

2. Solve Needs, Not Wants

Healthcare taught Allen the critical difference between "nice to have" and "must have." Products solving true needs become indispensable—customers can't imagine operating without them. Wants are vulnerable to budget cuts and competitive pressure. Ask yourself: if we removed this solution tomorrow, would it create genuine pain or just mild inconvenience?

3. Pilot Your Way to Trust in Skeptical Markets

In industries like healthcare where skepticism runs high and relationships matter, free pilots are worth their weight in gold. Allen shortens sales cycles and builds trust by offering 30-day no-cost pilots. Prospects experience both the product AND the support, building confidence that pays dividends when inevitable issues arise. In tight-knit markets, trust beats features every time.

4. Hire for Domain Expertise Over Sales Skills

Allen initially hired SaaS-savvy salespeople and trained them on healthcare. That didn't work. Healthcare sales requires understanding the ecosystem, knowing who to talk to, navigating 12-18 month cycles, and—crucially—having existing relationships. You can teach technology; you can't quickly teach 10 years of industry credibility. Hire seasoned professionals who already speak your customer's language.

5. Understand Timing and External Forces

In regulated industries, government decisions, new laws, and policy shifts can make or break your product overnight. Allen experienced this when Wisconsin threatened to roll out a state solution that could have eliminated his product's value proposition. Stay attuned to stakeholders beyond your customers: regulators, payers, associations. Build products resilient to foreseeable changes, and always have a Plan B.

6. Remote Culture Requires Intentional Connection

Video calls alone won't build deep trust. Allen learned that purely remote employees struggled to integrate into company culture. The solution: quarterly in-person gatherings for team building plus weekly virtual social hours (online games, cooking together) to break down surface-level barriers. Hybrid models work when you're intentional about creating shared experiences that help teams weather challenges together.

Guest Resources

allen@ancillaventures.com

www.ancillaventures.com

linkedin.com/in/allen-c00per

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