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Role Description

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.

• 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.
• Strategy & Planning
  • Contribute to the operations roadmap and annual planning processes.
  • Support goal-setting, benchmarking, and company-wide communications.
  • Develop as a trusted IC voice in planning and prioritization discussions.

Qualifications

• 3+ years of experience in a startup, management consultancy, or similarly fast-moving environment.
• Background in operations, analytics, or product preferred.
• Experience supporting a consumer-facing product is a plus.
• Strong bias toward action and iteration; comfort building imperfect systems and improving them over time.
• Excellent attention to detail and organizational skills, with the ability to manage multiple workstreams simultaneously.
• Comfort working with external partners across parallel initiatives.
• Strong SQL and Excel/Google Sheets experience.
• Familiarity with analytics tools such as Amplitude and Metabase.
• Clear, concise written and verbal communication skills.
• Experience in insurtech, Medicaid/Medicare, insurance brokerages, or adjacent regulated spaces is a big plus.

Requirements

• 3+ years of experience in a startup, management consultancy, or similarly fast-moving environment.
• Background in operations, analytics, or product preferred.
• Experience supporting a consumer-facing product is a plus.
• Strong bias toward action and iteration; comfort building imperfect systems and improving them over time.
• Excellent attention to detail and organizational skills, with the ability to manage multiple workstreams simultaneously.
• Comfort working with external partners across parallel initiatives.
• Strong SQL and Excel/Google Sheets experience.
• Familiarity with analytics tools such as Amplitude and Metabase.
• Clear, concise written and verbal communication skills.
• Experience in insurtech, Medicaid/Medicare, insurance brokerages, or adjacent regulated spaces is a big plus.

Benefits

• Meaningful work and a strong shared sense of mission.
• Remote-friendly work environment with a dog-friendly office in Downtown Brooklyn. The team meets in-person for optional retreats a few times per year.
• 20 Days of PTO.
• 4% 401K match.
• $10k lifetime spend towards Carrot Fertility.
• Excellent Medical, Dental and Vision options.
• Other health and mental health focused benefits and perks.
• Expected compensation for the role as scoped is $100,000 - 120,000 and will be based on how a candidate matches to our internal leveling guide.