Most of us assume that major hotel brands have sophisticated financial systems running behind the scenes. In this episode, Jess Conroy, CEO and co-founder of ROH, explains just how wrong that assumption is — and why she's spent the last several years building the financial core that hospitality never had.

What We Covered:

• The manual payments problem hiding in plain sight
• Why the biggest hotel brands have the biggest challenges
• The hidden complexity of every hotel transaction
• Why the hospitality industry was overlooked by fintech
• How ROH got its start in meetings and events
• What "AI-first" actually means at ROH
• How ROH fits into the existing hotel software stack
• The go-to-market reality of a franchise-heavy industry
• A transaction-based model that aligns incentives
• Scale and growth: managing over $1 billion across the portfolio
• The stale data problem driving bad hotel decisions
• The vision: a financial foundation for every hotel dollar

Key Takeaways

• Hotel payments are a solved problem almost everywhere except hospitality itself — the industry's bias toward "human solves" left it behind.
• The complexity of hotel transactions (variable pricing, upgrades, OTAs, group contracts) makes automation far more valuable here than in simpler retail or restaurant contexts.
• Building something that didn't exist before is the hardest sales motion — you're not replacing a known tool, you're educating a market about a problem they've learned to live with.
• Year-over-year expansion within existing hotels is the clearest signal of product-market fit — customers keep expanding their use once they're on the platform.

About Jess Conroy

Jess Conroy is the CEO and co-founder of ROH, a financial infrastructure platform for hotels. A second-time founder, she has spent nearly 15 years building in and around the hospitality industry. ROH is currently managing over $1 billion in hotel transactions across its growing portfolio.

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