Principal Customer Success Manager

OneSource Virtual

1d•Remote

About The Position

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.

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.

Nice To Haves

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.

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.