About Pylon America’s $13T mortgage market is one of the most important financial systems in the world. It underwrites the middle class and is the mechanism through which millions of families build wealth. But while every other financial instrument has been simplified to an API call, mortgages are still assembled by hand. We started from zero and created the first vertically integrated mortgage platform that turns origination into a single API. Publicly traded companies and the country’s largest originators are already building on Pylon. Revenue is compounding monthly. We’re backed by Peter Thiel, Conversion Capital, QED, Citi, Fifth Wall, and the founders of Ramp, Blend, and Mercury. Working at Pylon isn’t for those seeking comfort. The people who thrive here have high agency, strong opinions, and a track record of delivering outcomes without direction. Many of us are former founders. We move quickly, challenge each other directly, and take full ownership of results. It’s hard work, but it will be worth it. Join us in building America’s mortgage rails. ROLE OVERVIEW Pylon is building software-driven, real-time mortgage underwriting. Our Decisioning engine evaluates borrower data and underwriting guidelines to automate credit decisions that traditionally move through manual underwriting queues. As Head of Underwriting, you will bring the judgment of a world-class underwriting organization into that system. This is not a mandate to build a large conventional underwriting department. You will own the domain expertise, controls, exceptions, quality, and feedback loops that let Pylon safely automate more underwriting over time. RESPONSIBILITIES - Own underwriting domain expertise, quality, policy interpretation, and exception handling. - Review complex or unsupported scenarios and define how they should be handled going forward. - Translate underwriting guidelines and expert judgment into requirements Product and Engineering can encode into Pylon's Decisioning platform. - Identify recurring conditions, reviews, and escalations that should be automated or eliminated. - Establish QA, monitoring, override, and escalation mechanisms for automated decisions. - Partner closely with Processing, Compliance, Capital Markets, Account Management, Product, and Engineering. - Build metrics around automated decision coverage, manual-review rate, decision time, conditions, exceptions, overrides, and defects. - Help expand product and guideline coverage without sacrificing credit quality. QUALIFICATIONS - Significant mortgage underwriting and underwriting-leadership experience. - Strong preference for scaled wholesale lending experience. - Experience operating at hundreds or thousands of loans per month. - Excellent credit judgment and deep knowledge of underwriting guidelines and exceptions. - Ability to make implicit domain expertise explicit and systematic. - Strong process and quality orientation. - Comfortable working directly with technical teams in a rapidly evolving environment. WHAT SUCCESS LOOKS LIKE A growing percentage of Pylon loans receive fast, consistent decisions without routine manual underwriting. Human experts concentrate on genuinely difficult scenarios, automated decisions remain high quality, and every recurring manual judgment creates an opportunity to improve the Decisioning platform.