About the role
About Us Propel is on a mission to empower low-income Americans by simplifying access to government
benefits with modern technology. We're a passionate team of 100 Propellers - all working to help our users get through the month, every month.
The Role Propel owns Willoughby, a licensed entity building the first app-based digital Medicare brokerage, initially focused on dual Medicare-Medicaid users. We’re looking for a Senior Associate to help build and scale the operational foundation of our business. This is a highly cross-functional, individual-contributor role focused on automation, operations, analytics, and partner execution. You’ll work closely with Product, Engineering, Data, Compliance, and GTM to reduce manual work, improve reliability, and enable Propel to scale into new markets and partnerships. The core of what you’ll do Back Office Automation Build and own internal-facing tools that automate core backoffice and post-enrollment workflows Identify high-impact opportunities to reduce manual effort, improve accuracy, and increase operational efficiency Partner with Product and Engineering to scope, ship, and iterate quickly on automation Operations & Partnerships Support and increasingly own key operational partner relationships, including FMOs Manage carrier contracting and onboarding to enable GTM and state expansion Build, maintain, and refine Intercom workflows and macros to support advisors effectively at scale Data & Analytics Use tools like Amplitude , Metabase , SQL , and spreadsheets to understand and improve Propel’s funnel Partner with Product, Engineering, and Data to translate insights into execution and prioritization Develop strong intuition for operational metrics and business performance Compliance Partner with the CCO and our compliance consultant on annual compliance filings Support compliance incident response and enrollment QA, automating processes where possible Ensure compliance processes scale cleanly as the business grows