Director of Customer Success (Enterprise)

About Us Capitalize is building critical infrastructure for the $20 trillion retirement savings market with scalable technology and a world-class team. We’re bringing a digital, API-first approach to modernize the $1 trillion in retirement account transfers (401(k) rollovers) that happen annually. By doing so, we’re helping the almost 20 million Americans who change jobs each year with a 401(k) do the right thing with their assets. . Our Enterprise offering includes a full suite of APIs used by leading financial institutions such as Robinhood, Betterment, SoFi, TIAA, Morgan Stanley, and many more. Our recently launched Advisor offering helps wealth management firms and advisors leverage that same technology, helping end-users seamlessly find and consolidate their retirement savings into one account. We’ve raised $35mm from leading venture capital investors including RRE Ventures, Canapi Ventures, Greycroft, and others, and we’ve been recognized as one of TIME’s 100 Best Inventions, one of the Most Innovative Companies in America by Fast Company, and by Forbes as one of the Top 50 Fintech Companies in the US for several years running. About the Role Our Enterprise business is scaling rapidly as our Rollover API is being quickly adopted by more of the industry to drive asset growth and better transfers. We’ve more than tripled the number of Enterprise clients in the last 18 months and we’re growing fast. We’re hiring a Director of Customer Success (Enterprise) to help new Enterprise clients succeed and drive retention, expansion, and long-term growth. This role sits at the intersection of revenue, product, and operations. You’ll own key Enterprise client relationships, and work closely with Product, Engineering, and Operations to ensure a tight feedback loop between client feedback, product development, and revenue growth. What You’ll Do Be a strategic partner to Enterprise clients Build trusted relationships with product, operations, and business leaders at our Enterprise clients Lead structured business reviews grounded in data, outcomes, and clear next steps Act as the internal voice of our Enterprise client, ensuring their needs are clearly understood and addressed by the company Help drive launch and growing usage of our APIs Ensure newly signed Enterprise clients launch successfully along with others in the organization Reduce time-to-value by improving how partners integrate, go live, and scale usage Help optimize integrations and product placements once launched Own retention and support expansion Own key retention goals for relevant Enterprise clients, proactively ensuring client delight and successful renewals Identify and support expansion opportunities across clients, use cases, and product surfaces Build visibility into renewal risk and expansion pipeline Drive cross-functional alignment Partner closely with Sales on account strategy, deal support, and expansion opportunities Work with Product and Engineering to translate client feedback into roadmap priorities and platform improvements Collaborate with Operations and Analytics to track partner performance and identify areas for optimization What You’ll Bring Must-Have 8+ years in Customer Success, Account Management, or post-sale leadership in B2B SaaS, fintech, or enterprise software Experience owning or materially impacting retention and expansion metrics (NRR, GRR, upsell/cross-sell) Track record of working successfully in high-growth environments Strong experience working with Enterprise clients, including senior product, operations, and business stakeholders Strong analytical mindset, comfortable using data to drive decisions and prioritize work Working Style High ownership and accountability, you take responsibility for outcomes, not just activity Structured thinker who can bring clarity to complexity Comfortable operating in ambiguity and building from the ground up Strong cross-functional collaborator who can align teams around shared goals Nice to Have Experience in fintech, wealth management, or financial infrastructure Experience working with API-based or integration-dependent products Background in regulated or compliance-driven environments Experience in rapidly scaling companies Perks Competitive salary and equity Medical, dental, and vision insurance, with 100% premium covered for employees and 50% for dependents 401(k) plan access Unlimited paid time off 12 weeks of fully-paid parental leave Compensation based on leveling: Director: $140K - $160K Base Salary Annual variable bonus based on performance Why Join Us We’re a mission-driven company focused on doing what’s right—for our customers and for our team. That means assembling a diverse, hardworking group of people who want to be their best in an open and inclusive environment. We believe that a diverse, equitable, and inclusive company enriches both our professional and personal lives. If that speaks to you, we want to meet you.