Managing $10 billion in loans teaches you a lot about what truly drives repayment and performance. In this episode of Leaders in Lending, host Lynn Sautter Beal sits down with Jesse Obbink, vice president and general manager of servicing at Upstart, to break down the operational, analytical and human insights that matter most once a loan is on the books.

Jesse shares why servicing is “underwriting with an operational twist,” how data and machine learning help shape borrower outcomes and why empathy often outperforms traditional collections tactics. They also discuss what scale unlocks, how to manage dozens of vendor relationships effectively and how LLMs are transforming frontline agent workflows.

Whether you lead a credit union, bank or fintech, this conversation reframes servicing as a strategic lever for reducing losses, improving repayment and strengthening long-term performance.