Principal Customer Success Manager
About the role
OneSource Virtual (OSV) has worked exclusively with Workday customers since 2008 to deliver compliant, in-tenant technology and expert services to automate the administrative, transactional tasks of payroll, taxes, earned wage access, accounts payable, and benefits. With over 1,500 customers, 92% retention, and $225+ billion in treasury movement annually, OSV helps organizations maximize their Workday investment and operate it with confidence. Payroll, benefits, and finance solutions — all in one place.
Job Summary
Senior strategic advisor responsible for driving high retention, expansion, and payment solution adoption across a portfolio of key executive, high-value OSV Financial and Accounting Services clients. The ideal candidate is deeply customer-centric — cultivating executive-level trust and turning clients into long-term partners and advocates.
The ideal candidate brings robust experience in Commercial Payments, with the ability to consult clients on optimizing disbursement workflows, Virtual Card adoption, payment monetization strategies, and Workday-integrated payment solutions. This is not a passive account management role — we are looking for a results-driven leader who sets high standards, holds themselves accountable to portfolio metrics, and brings urgency, creativity, and thought leadership to every client engagement.
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.
Qualifications
Required
Experience: 15+ years in Customer Success, Account Management, Sales, or Consulting with a focus on enterprise solutions and Commercial Payments.
Payments Expertise: Deep experience in Commercial Payments, Virtual Card, disbursement workflows, or financial operations as a practitioner or advisor. Fintech or banking background a strong plus.
Leadership: Strong ability to influence cross-functional teams and senior stakeholders without direct authority.
Analytical Skills: Proficient in using data and analytics to monitor health scores, identify trends, and drive action.
Communication: Excellent executive communication and presentation skills.
Commercial Acumen: Experience with upsell pipelines, P&L impact, and contract negotiations. Proficiency with Salesforce or comparable CRM.
Technical Acumen: Ability to understand complex payment and technology challenges and guide clients toward effective solutions.
Preferred
Workday: Workday ecosystem experience (Financials).
Agility: Ability to thrive in an evolving, high-growth environment with corporate professionalism and agility in equal measure.
Background: Experience in a PE-backed technology or services company.
#LI-REMOTE
You are encouraged to learn and share ideas when you join the OneSource Virtual team. We reward innovative thinking, fresh perspectives, creative collaboration, and hard work. As an organization experiencing routine strategic growth, we are always on the lookout for intelligent, talented, and forward-thinking professionals to join our team. OSV employees enjoy a values-based culture, upward mobility, and professional development with opportunities of all kinds.
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