About Flex Flex was founded to solve a simple but costly problem: making it easy for health and wellness brands to accept HSA and FSA payments online. For years, only giants like Amazon and Walmart could process these payments at checkout, leaving smaller merchants — and their customers — to deal with frustrating reimbursement paperwork. Our technology verifies product eligibility in real time, handles split payments for eligible and non-eligible items, and can even issue Letters of Medical Necessity during checkout. With $150 billion in annual HSA/FSA spending potential, we’re giving brands the tools to unlock new revenue and making it easier for consumers to use the benefits they’ve earned. About the Role We’re hiring a Customer Success Manager to own post-sale relationships with our enterprise and mid-market merchants. You’ll be the primary point of contact for assigned accounts—driving adoption, retention, renewals, and expansion. This role is perfect for someone with a strong account management background (5+ years), ideally in payments, ecommerce, or subscription technology (BNPL, Stripe, Bolt, Skio, etc.). We’re looking for a proactive partner who can guide customers through growth, bring strategic insight to the table, and thrive in a high-growth startup environment. What You’ll Do • Customer Relationship Ownership: Serve as the primary point of contact for assigned accounts post-sale. Build and nurture relationships at multiple levels, from day-to-day users to executive sponsors. Act as the “face of Flex” for all commercial conversations. • Retention & Renewal: Own the renewal process, including timelines, pricing, negotiation, and signatures. Monitor account health, escalate risks internally, and build remediation plans to reduce churn. • Expansion & Revenue Growth: Identify upsell and cross-sell opportunities within accounts and partner with Sales on larger or complex expansions. Align Flex’s capabilities to customer goals to justify increased spend. • Account Planning & Strategy: Maintain detailed account plans (org charts, KPIs, risks, whitespace). Run QBRs/EBRs to review value realized and set next-phase objectives. Provide accurate forecasts on renewals and expansion for revenue planning. • Cross-Functional Coordination: Orchestrate resources across Support, Product, CS, Marketing, and Execs. Act as the voice of the customer internally, surfacing product feedback and market insights. Coordinate resolution of escalations with Support/Dev teams. • Program & Process Execution: Ensure smooth onboarding handoffs from Sales/Implementation to steady-state. Document customer activity, health, and pipeline rigorously in CRM. Track adoption, usage, and ROI metrics; turn data into actionable recommendations. • Communication & Reporting: Provide clear and consistent communication to customers (project updates, product changes, best practices). Prepare internal reporting on account health, renewal likelihood, and revenue at risk. Manage executive updates internally (leadership reviews, board prep, etc.). Who You Are • 5+ years of enterprise or strategic account management / customer success experience with a proven record of retention and expansion. • Experience working with ecommerce or payments brands (BNPL, Stripe, Bolt, subscription platforms like Skio) strongly preferred. • Track record of managing multi-stakeholder, high-value accounts at scale. • Excellent relationship-building and executive communication skills. • Comfortable with CRM rigor, forecasting, and data-driven account health tracking. • Thrive in a high-growth, fast-paced environment and enjoy building processes from scratch. • Willingness to travel for customer meetings, conferences, and company offsites (~20%). Mindset • Low ego — open to feedback and growth. • Collaborative — thrive in cross-functional team settings. • Hustler — put in the effort required to make things happen. • Self-starter — quick to learn new technologies and skills. Why Join Flex • Backed by Y Combinator, First Round Capital, Core Innovation Capital, and SV Angel. • Competitive compensation, equity, and unlimited PTO. • Health, dental, and vision insurance for employees. • Opportunity to work alongside a hard-working, high-performance team that celebrates wins together. • Company offsites a few times per year to build relationships and shape strategy. • Direct impact on customer success, revenue, and strategic partnerships. Flex is an equal opportunity employer and encourages applicants from all backgrounds and life experiences. We celebrate diversity and do not discriminate based on race, religion, color, national origin, sexual orientation, gender identity, gender expression, age, veteran status, disability status, or any other legally protected characteristic.