In this episode, Host Taylor Baker sits down with Caleb Avery, CEO and founder of Tilled, to discuss how embedded payments and PayFac-as-a-Service are changing the way vertical SaaS companies monetize payments and what it takes to build a fast-growing fintech platform while scaling leadership, teams, and life outside the business.
What You’ll Learn
- Why many vertical software companies outgrow “one-size-fits-all” payment providers and start looking for better support, branding control, and economics.
- How PayFac-as-a-Service helps software platforms monetize payments without taking on the full operational and compliance burden alone.
- What Caleb learned from starting in payments at 19, and how early frontline selling shaped his understanding of customer pain.
- How to spot recurring market friction through consulting and advisory work, then turn it into a scalable product opportunity.
- Why hiring mistakes are often the most expensive lessons for first-time CEOs, and how cultural fit can matter as much as skill set in small teams.
- What it looks like to scale a venture-backed business while staying disciplined about focus, priorities, and execution.
- How to balance the demands of building a high-growth company with raising a young family—and the trade-offs founders should expect.
- Why tightening onboarding and “first 90 days” playbooks can be a major lever for enterprise partnerships and long-term retention.terprise.
Caleb’s story highlights the power of building where you have deep domain expertise, listening for repeated customer frustrations, and designing a solution that improves both outcomes and experience for software platforms. The conversation reinforces that sustainable growth comes from product clarity, strong partnerships, intentional hiring, and the willingness to make hard trade-offs as the company—and the founder—scales.
To learn more about Caleb Avery and their work.