Full-Time
Job Posting: VP of Customer Success — North America
Job Title: VP of Customer Success
Company: Checkout.com
Location: Chicago, IL (Remote / Hybrid)
Industry: Financial Technology / Enterprise Software
Employment Type: Full-time
【About the Role】
Checkout.com is seeking a high-impact VP of Customer Success to lead our regional relationship management and growth strategy from our Chicago hub. In this executive-level role, you will be responsible for the health, retention, and strategic expansion of our premier North American enterprise portfolio.
You will lead a team of high-performing Success Managers, ensuring that the world’s most sophisticated digital brands receive the technical excellence and strategic consultation they need to scale globally.
【Key Responsibilities】
Portfolio Strategy: Direct the overarching Customer Success strategy for North America, focusing on net revenue retention (NRR) and long-term partnership value.
Operational Excellence: Build and scale a world-class success organization, implementing data-driven frameworks to monitor merchant health and performance.
Executive Advocacy: Serve as the senior-level liaison for C-suite stakeholders within our global merchant base, aligning our technical roadmap with their business objectives.
Cross-Functional Collaboration: Partner closely with Sales, Product, and Engineering teams to advocate for customer needs and streamline the integration of next-gen payment solutions.
Talent Leadership: Mentor and grow the Chicago-based success team, fostering a culture of obsession with customer outcomes and technical precision.
【Who You Are】
Seasoned Leader: 10+ years of experience in Customer Success or Account Management within the Fintech, Payments, or Enterprise SaaS sectors.
Scale Specialist: Proven track record of leading organizations through rapid growth phases, managing portfolios with billions in transaction volume.
Technical Acumen: A deep understanding of global payment rails, financial infrastructure, and API-driven service models.
Strategic Communicator: Exceptional ability to navigate complex organizational structures and build trust with institutional leaders.
Midwest Hub Expert: Passionate about leveraging Chicago’s talent pool and financial ecosystem to drive regional success.
【Why Join Checkout.com?】
Lead the customer-centric mission for a global, profitable fintech leader.
Manage relationships with some of the most iconic brands in the global digital economy.
Direct impact on the company’s North American growth trajectory.
Flexible executive-level role based in Chicago, the center of American commercial innovation.