Payroll Tax Implementation Lead

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 Implementation Lead is responsible for the successful onboarding of customers — from initial discovery through go-live. This role requires deep payroll tax expertise combined with strong project management and consultative skills, applied to translate each customer's organizational structure, jurisdictional requirements, and tax data into a precisely configured payroll tax environment.

This role is responsible for executing implementations with precision while contributing to the development of methodologies, documentation, and product intelligence that will define how the team scales its implementations.

Implementation Ownership

• Own end-to-end implementation of customer and tax setup from kickoff through go-live – managing toward timelines, milestones, open items, and tax-related customer communication throughout.
• Serve as the customer’s primary tax expert contact, building trust through clear guidance, consistent follow-through, and expert knowledge of the tax landscape and applicable systems.
• Helps maintain organized documentation (decisions log, data status, open items) based on inputs from customer conversations regarding the customer and tax setup strategy and needs.

Discovery, Configuration & Data

• Lead discovery to understand each customer's organizational hierarchy, jurisdictional requirements, and tax data structure.
• Configure the system based on discovery findings – hierarchy setup, tax code mapping, filer relationships, and system parameters – tailored precisely to each customer’s filing and payment needs.
• Guide customers through key configuration decisions, advising on how structure and setup choices will affect their day-to-day workflows.
• Assess incoming customer tax data for completeness and accuracy and perform as-needed data action and analyses to keep the implementation time frame moving at the appropriate pace.
• Load and validate historical payroll tax data, reconciling against customer records to ensure accuracy before go-live, working with technical leads as needed.

Cross-Functional & Training Collaboration

• Partner with Engineering, Product, Compliance, and Sales to resolve blockers and ensure each implementation has the internal support it needs.
• Work closely with the Training team to support a clean knowledge handoff at go-live – sharing configuration context and customer-specific decisions that inform effective training.
• Feed implementation learnings – product gaps, recurring friction points, configuration edge cases – back to Product and Training to strengthen methodology and materials over time.
• Act as an expert voice at critical points during the sales cycle where deeper discovery and configuration knowledge matter most, joining select prospect conversations to answer deeper questions, build credibility, and help prospects understand how the solution would function for them.

Required

• 10+ years in payroll, payroll tax, or tax operations with multi-jurisdictional expertise; deep, current knowledge of payroll tax regulations, agency requirements, and filing and payment processes across multiple jurisdictions;
• Hands-on experience configuring or implementing payroll tax software – system setup, data loading, tax code mapping, and filing hierarchy configuration.
• Strong analytical ability: able to assess complex tax datasets for accuracy, gaps, and proper structure.
• Clear communicator – able to translate technical and tax concepts for both technical teams and non-technical customer stakeholders.
• Self-starter comfortable with building processes in ambiguous environments.
• Demonstrated ability to collaborate across functions – including Engineering, Product, and Compliance – to drive customer outcomes.
• Consultative nature – able to be a trusted advisor to customers, guiding them through complex configuration and data decisions with clarity and credibility.

Preferred

• Experience with HCM platforms (UKG, SAP SuccessFactors, Workday, Dayforce, PeopleSoft, ADP) in implementation contexts.
• Background with HCM resellers, payroll service bureaus, or multi-client payroll environments.
• Familiarity with implementation methodologies or project management frameworks (PMP, Agile).
• Experience with comparable end-to-end payroll tax filing, reconciliation, and treasury platforms.
• 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.