Job Description

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.

The Payroll Tax SME & Knowledge Expert is the internal authority on payroll tax. This role is deployed where the depth of tax expertise creates the most leverage: complex configuration decisions, escalated issues, high-stakes pre-sales conversations, and product advisory. The SME is available to Implementation, Enablement, Sales, and Product whenever a genuine tax authority is required.

This role also carries responsibility for the long-term tax knowledge of the team. Working closely with the Training team, the SME also ensures that complex tax knowledge is translated into training content, configuration guides, and decision frameworks that scale beyond any single conversation.

Product Management

• Serve as the primary tax SME for Product and Engineering – ensuring features and logic are consistent with current regulations.
• Translate customer and prospect feedback into prioritized product enhancement recommendations for consideration on the tax product roadmap.
• Assist product leaders in prioritizing product initiatives and aligning engineering teams to execute key roadmap initiatives.
• Participate in UAT to validate new releases against real-world tax scenarios across applicable customers and environments.
• Assist in problem-solving complex or escalated customer issues spanning implementation, data mapping, file exports, agency interactions, and software usage, providing resolution with the authority of someone who understands both the tax rules and the underlying systems deeply.
• Feed product learnings and market information back into the customer story/marketing assets to maximize the product’s differentiation and impact on the market.

Customer Advisory

• Advise customers on complex tax configurations, best-practice usage, and escalated issues spanning data mapping, file exports, and agency interactions.
• Handle one-off advisory requests – data reviews, scenario-specific guidance – that fall outside standard support workflows.
• Act as an expert voice at critical points during the sales cycle where expertise can be highly leveraged; join select prospect conversations to answer deeper tax questions, build credibility, and help prospects understand how the solution addresses their specific tax challenges.
• Assist in building and testing demo environments as needed that accurately represent product and service capabilities, ensuring demos are current, technically sound, and tuned to the audience.

Knowledge & Training Contribution

• Work closely with the Training team to translate deep tax and product knowledge into training content, configuration guides, and decision frameworks that scale the team's capabilities.
• Interface with GTM, Sales, Support, Compliance, and Operations as the go-to tax knowledge resource – making complex knowledge accessible and actionable for each audience.
• Stay current on federal, state, and local payroll tax regulatory changes and proactively communicate relevant updates to Product, Compliance, and customer-facing teams.

• Configuration decisions requiring deep tax judgment – complex hierarchy structures, multi-jurisdiction edge cases, non-standard filer relationships.
• Escalated customer issues spanning implementation, data mapping, file exports, or agency interactions that require both tax expertise and technical depth.
• Pre-sales conversations where complex tax requirements make the credibility of deep expertise essential to advancing the deal.
• Product advisory – feature design reviews, UAT, and feedback on functionality with payroll tax compliance implications.
• Prospects – as an expert voice at critical times to help move forward the sales cycle.
• Regulatory changes requiring proactive communication to customers, Product, or Compliance.
• One-off customer advisory requests outside standard workflows – data reviews, scenario-specific guidance, or strategic configuration planning.

Required

• 12+ years in payroll, payroll tax, or tax operations with mastery of multi-jurisdictional payroll tax regulations, agency requirements, and filing and payment processes.
• Deep, current knowledge of federal, state, and local payroll tax regulations and how they map to software configuration decisions and customer/market challenges.
• Hands-on experience with payroll tax or HCM software at a functional depth beyond end-user familiarity.
• Demonstrated ability to translate complex tax knowledge into clear, credible communication for diverse audiences.
• Experience in customer-facing or advisory roles, with the presence to influence high-stakes product decisions.
• Direct experience with end-to-end payroll tax filing software and services, impoundment, payment, and reconciliation platforms.

Preferred

• Experience with HCM platforms (UKG, SAP SuccessFactors, Workday, PeopleSoft) in payroll tax configuration contexts.
• Background working with HCM resellers, payroll service bureaus, or multi-employer environments.
• Experience in software UAT in a tax or compliance product context.
• Exposure to sales cycles, pre-sales engineering, or solution consulting.
• Professional certification: CPP (Certified Payroll Professional) or FPC.
• Bachelor's degree in Business, Accounting, Finance, or related field.

#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.