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

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

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

At Propel, you'll enjoy:

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
Propel builds compensation bands referencing the 75th percentile of compensation for companies like us. 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.

Additional Considerations:

We are committed to building a diverse and inclusive team, and welcome applicants from all backgrounds and abilities.
Interview Accommodations: Propel is committed to providing reasonable accommodations throughout the interview process. If you need accommodations due to a disability or medical condition (such as additional time or accessibility support), please let us know as early as possible so we can support you appropriately.
We're currently accepting applications from the states we have an established entity, which includes California, Colorado, District of Columbia, Florida, Georgia, Illinois, Maryland, Massachusetts, New Jersey, New York, Oregon, Pennsylvania, Texas, Virginia, and Washington.
Background Check Requirement: For roles with access to confidential employee or customer information, a background check may be conducted following a conditional offer. All background checks are handled in accordance with applicable laws, including the Fair Credit Reporting Act (FCRA).

More About Propel

Propel is a technology company that’s strengthening the social safety net for people who receive government benefits. Over 5 million Americans trust the free, modern Propel app to manage their government benefits, save money, and get updates when their benefits change. We’ve also partnered with renowned institutions and organizations like Vote.org, GoFundMe, and GiveDirectly.

Propel is a for-profit, venture-backed company that holds its social mission at its core. We're proud to be supported by a blend of nonprofits, impact investors, and world-class investors, including the Robin Hood Foundation, Andreessen Horowitz, Nyca Partners, Financial Health Network, JPMorganChase, Kevin Durant, Serena Williams, and Nas.

Learn more about our impact from the press

Join us, and let's build something amazing together!

Senior Insurance Brokerage Operations Associate

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