Hiring: Head of Underwriting Company: Pylon Location: New York, NY Job Posted Time: 2026-09-16 12:03:38 Target Skills & Keywords : Capital Markets, Rails About the job Required Skills: •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. •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. Qualifications: •Significant mortgage underwriting and underwriting-leadership experience. •Strong preference for scaled wholesale lending experience. •Excellent credit judgment and deep knowledge of underwriting guidelines and exceptions. •Demonstrated capacity to make implicit domain expertise explicit and systematic. •Strong process and quality orientation. •Comfortable working directly with technical teams in a rapidly evolving environment. •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. Interested candidates, please apply directly through the job posting on company's career page or try via AI auto apply on this platform. Don't miss this opportunity to join a forward-thinking team!