Director of Customer Success (Enterprise)

Capitalize

$140K — $160K *
Enterprise Technology
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 8+ years in Customer Success, Account Management, or post-sale leadership in B2B SaaS or fintech
  • Experience owning or impacting retention and expansion metrics (NRR, GRR, upsell/cross-sell)
  • Proven success in high-growth company environments
  • Strong background with senior product, operations, and business leaders in Enterprise clients
  • Analytical mindset for data-driven decision making

Responsibilities

  • Build trusted relationships with leaders at Enterprise clients
  • Lead structured business reviews grounded in data and clear next steps
  • Act as the internal voice of Enterprise clients' needs
  • Ensure successful launches of new Enterprise clients
  • Reduce time-to-value by optimizing client integration processes
  • Own key retention goals and proactively ensure client renewals
  • Partner with Sales for account strategy and expansion opportunities

Benefits

  • Medical, dental, and vision insurance with full employee premium coverage
  • 401(k) plan access
  • Unlimited paid time off
  • 12 weeks of fully-paid parental leave
Full Job Description
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

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