Principal Customer Success Manager

OneSource Virtual (OSV) has been a trusted partner for Workday customers since 2008, providing expert services and technology solutions. The Principal Customer Success Manager will serve as a senior strategic advisor, focusing on driving retention, expansion, and payment solution adoption for key clients, while building executive-level relationships and mentoring junior team members.

Responsibilities:

• Strategic Account Management: Define and execute success plans for complex, high-value clients to drive maximum value, long-term ROI, and payment optimization outcomes
• Retention & Growth: Own a portfolio of strategic accounts, delivering against NRR and expansion targets. Identify upsell/cross-sell opportunities and mitigate churn risk early
• Payment Optimization: Lead client conversations on disbursement optimization, payment waterfall, Virtual Card adoption, monetization strategies, and Workday-integrated payment workflows. Partner with Product and Technology to represent client needs and influence the roadmap
• Executive Relationship Building: Establish trust with C-level stakeholders across Finance, Procurement, Supply Chain, and AP. Lead Strategic Business Reviews (SBRs) and serve as an escalation point for service issues
• Cross-Functional Leadership: Partner with Sales, Product, and Support teams to align client goals with internal initiatives. Report portfolio health and growth to the Director, Customer Office
• Customer Advocacy & Thought Leadership: Champion client needs, providing insights for product roadmaps, and serving as an expert on payment industry best practices
• Mentorship: Mentor junior CSMs and help define customer success disciplines, tools, and processes across the organization

Requirements:

• 15+ years in Customer Success, Account Management, Sales, or Consulting with a focus on enterprise solutions and Commercial Payments
• Deep experience in Commercial Payments, Virtual Card, disbursement workflows, or financial operations as a practitioner or advisor. Fintech or banking background a strong plus
• Strong ability to influence cross-functional teams and senior stakeholders without direct authority
• Proficient in using data and analytics to monitor health scores, identify trends, and drive action
• Excellent executive communication and presentation skills
• Experience with upsell pipelines, P&L impact, and contract negotiations. Proficiency with Salesforce or comparable CRM
• Ability to understand complex payment and technology challenges and guide clients toward effective solutions
• Workday ecosystem experience (Financials)
• Ability to thrive in an evolving, high-growth environment with corporate professionalism and agility in equal measure
• Experience in a PE-backed technology or services company