Propel

Build and optimize automation tools, support operational partnerships, analyze data to improve business performance, and ensure compliance in a fast-paced startup environment. | Requires 3+ years in operations, analytics, or product support, with strong SQL and Excel skills, and experience supporting consumer-facing products, ideally in regulated spaces like insurtech or healthcare. | 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 Fintech Company Propel Announces $10 Million Fund For Food Stamp Late Show With Stephen Colbert How to Propel the Fight Against Poverty in America How Tech is Helping Poor People Get Government Aid Propel Routes Money to those Who Need it Most How one tech startup is giving cash to SNAP recipients Recipients Affected By Government Shutdown How hunger relief groups say you can help feed your neighbors during the shutdown and beyond Helping our Users Navigate this Crisis Join us, and let's build something amazing together!

Own and elevate the end-to-end Marketplace experience, defining strategy, leading design execution, and collaborating across teams to drive engagement and trust. | Over 10 years of product design experience, proven success in consumer discovery/browsing experiences, strong leadership skills, and ability to operate autonomously in fast-paced environments. | About Propel Propel is on a mission to build technology that strengthens the social safety net. We’re a passionate team of ~100 Propellers who envision a future where every American has the tools and resources they need to thrive. Position Overview We’re looking for a Marketplace Design Lead to own and elevate the end-to-end Marketplace product experience at Propel, reporting into our VP of Design. This person will set a clear design strategy and long-term vision for Marketplace, while also staying close to execution as a player/coach. Marketplace is a critical surface area for Propel — it’s where we help millions of low-income Americans discover and access products and services that can meaningfully improve their lives. This role will partner closely with senior leaders across Business, Product, Engineering, and Brand to build a Marketplace that feels personalized, opinionated, and high-trust, while driving measurable outcomes across engagement and revenue. What you’ll do: Own the end-to-end Marketplace user experience — from discovery and strategy through detailed execution — shipping high-quality, accessible product experiences. Define and drive Marketplace design strategy and vision, aligning cross-functional partners on what “great” looks like in the short-term and long-term. Build a Marketplace that feels personalized and opinionated, helping users quickly find the right offers with clarity and confidence — not just browse a generic catalog. Design for trust, clarity, and decision-making, ensuring Marketplace experiences are credible, easy to understand, and built for real-world constraints. Partner deeply with Product, Engineering, and Data to define goals, prioritize the roadmap, run experiments, and iterate quickly based on performance and user insights. Scale Marketplace into new verticals and categories, including Propel-branded products and services, while keeping the experience coherent and consistent. Raise the bar on craft and quality, through strong design direction, critique, and hands-on contributions to key flows and experiences. Help shape the Marketplace design team over time, including identifying skill gaps, supporting hiring, and setting a strong operating rhythm for execution. What you need: 10+ years of product design experience, including ownership of complex product areas from strategy through launch Strong track record designing consumer experiences centered on discovery and browsing (e.g., marketplaces, commerce, travel, media, content-heavy products, etc.) Proven ability to set a clear product/design vision and translate it into shippable work in fast-moving, ambiguous environments Excellent judgment balancing user needs, business goals, and long-term trust High craft bar — strong interaction design, visual polish, and attention to detail that raises the quality of what ships Strong cross-functional leadership skills — you can operate as a senior partner to Product and Engineering, align stakeholders, and move decisions forward Clear, compelling communicator — you can tell the story, make tradeoffs understandable, and bring teams along High ownership and autonomy — you operate like an owner, look around corners, and make smart local decisions Big plus: People management experience (leading small teams, player/coach roles) Comfort prototyping and vibe coding with emerging design and AI tools 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. 20 Days of PTO 4% 401K match $10k lifetime spend towards Carrot Fertility Excellent Medical, Dental and Vision options A strong equity package that reflects the leveling and anticipated impact of this role Propel builds compensation bands referencing the 75th percentile of compensation for companies like us. Expected compensation for the role as scoped is $215,000 - $265,000 and will be based on how a candidate matches to our internal leveling guide. Bands may be expanded if someone is leveled more senior than the role was initially scoped. Additional Considerations: We are committed to building a diverse and inclusive team, and welcome applicants from all backgrounds and abilities. We're currently accepting applications from the states we have an established entity in, 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 Fintech Company Propel Announces $10 Million Fund For Food Stamp Late Show With Stephen Colbert How to Propel the Fight Against Poverty in America How Tech is Helping Poor People Get Government Aid Propel Routes Money to those Who Need it Most How one tech startup is giving cash to SNAP recipients Recipients Affected By Government Shutdown How hunger relief groups say you can help feed your neighbors during the shutdown and beyond Helping our Users Navigate this Crisis Join us, and let's build something amazing together!

Lead and scale a high-performing customer success team, drive client strategy and revenue growth, align cross-functional teams, and build scalable systems for customer success in a marketplace environment. | 10+ years customer success/account management in high-growth startups, 5+ years consultative sales for marketplace products, 3+ years managing account teams, strong product and data-driven mindset, and passion for social mission. | 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 Are you looking to make a big impact on an early-stage company? Does the thought of scaling an innovative technology business solving real problems for an underserved community excite you? Do you excel at building and leading strong, high-performing teams? We launched the Propel Marketplace to connect our ~5M monthly active users to products, services, and exclusive offers from leading brands across retail, healthcare, and financial services. It has grown into a powerful, industry-leading performance tool for our partners and a critical revenue driver for Propel. We’re looking for an exceptional Head of Customer Success to help take this business to the next level and by driving client performance and revenue. This role is an ideal fit for someone who has a strong product and data driven mindset, and enjoys the challenges of aligning our internal systems and external partners together to drive us towards growth. You’ll also be a part of a strong leadership team - you’ll work closely with our VP of Marketplace, Director of Strategy and Operations, Director of Sales and BD, and Director of Growth and Merchandising. In this role, you'll have an outsized impact on our growth and success. Here's a taste of the type of work you will lead: Drive our client strategy. Partner with CSMs to refine account strategies and ensure we hit ambitious annual growth targets across existing accounts. Design and implement GTM playbooks (pricing, QBRs, etc). Lead on GTM narratives and pitches when launching new products and initiatives. Lead a high-performing team. Coach our team of Customer Success Managers (CSMs) as they set account strategies, handle complex client situations, and seek opportunities to grow revenue. Support team growth and career development while establishing clear performance standards so team members know when they are exceeding, meeting, or falling short of expectations. Align GTM and Stakeholder Priorities. Build strong relationships with Sales, Marketing, Product, and Design teams to deliver results. Advocate for the customer success team’s interests and needs with cross functional partners. Manage and protect the customer success team’s time, bandwidth, and focus. Own and scale our systems. Work with Product to identify tools and platform improvements that help scale excellent customer experiences. Work with BizOps and Data to develop practices and processes for analytical problem-solving, insights, and reporting. Build systems to advise customers on campaign setup, optimization, and growth. Set the targets. Establish goals that push the team to a new level of growth and success, with metrics to measure individual and team performance. Partner with BizOps to ensure account-level goals ladder up to ambitious but achievable team targets. Drive us forward: Deliver account-level reporting to leadership that ensures we have a strong understanding of the health of the business and high-fidelity forecasts. Own a 12-month hiring plan to align with segmentation, portfolio balance, and business development pipeline. Requirements: A strong product mindset - experience driving alignment across sales, marketing, engineering, and product to deliver results and a willingness to get your hands dirty to understand our internal systems and tools 10+ years of customer success, account management, or partnership experience in a high-growth start-up environment 5+ years of driving consultative sales experience for a two sided Marketplace product 3+ years of experience leading and managing an account management team with varying degrees of experience (junior to senior level) A proven self-starter comfortable navigating ambiguity Deep knowledge of customer success best practices and experience coaching others Existing knowledge or ability to quickly learn vertical-specific trends, business models, market opportunities, and metrics A data driven mindset - strong problem-solving and quantitative analytical skills Passion for building a business with a strong social mission at the intersection of private and public sectors We Offer: An immediate opportunity to make an impact on our users and the business we’re building. A get-stuff-done culture that is also fun and caring. Work that really is helping people with meaningful challenges A remote-first working environment with headquarters in Brooklyn and satellite offices in San Francisco, Los Angeles, and Salt Lake City. Propel believes that everyone should be compensated fairly and equitably. We set our salary ranges using compensation data from hundreds of NYC based startups at our stage. Additionally, pay is not determined based on location. The salary range for this position is $200,000 - $240,000, depending on experience. A 10% bonus for team performance, equity and excellent benefits come with this position as well! Here’s how our role is different: Propel’s Marketplace is a critical revenue driver for the company and this role will play an instrumental role in taking this business to the next level. With no comparable platform in the market, this person will help redefine how low-income Americans access products and services by working with leading brands across retail, healthcare, and financial services. More About Propel We believe that Americans with limited income deserve modern, respectful, and effective experiences around their government benefits and money. Unfortunately, the status quo often fails to treat them as first-class citizens in their daily interactions around the social safety net and financial services. The tech industry hasn’t pulled its weight in solving the problems faced by low-income Americans. Propel’s mission is to change that. We’ve built Providers, the single most popular app in the country built specifically for low-income Americans. Over 5 million families each month use Providers to seamlessly manage their government benefits (programs like SNAP, commonly known as food stamps), conduct their banking, and save and earn money. Providers has been recognized by the White House, featured on the front page of the NY Times, and carries over 500,000 five star reviews. 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. Join us, and let's build something amazing together!