Director, Payroll & Tax Implementation

A strategic operations leader who balances deep regulatory rigor with a commercial, growth-oriented mindset. You view payroll and tax implementation as a strategic asset that accelerates growth channels and enables GTM success. You bridge the gap between complex tax compliance and commercial scalability, ensuring operational excellence becomes a competitive advantage.

Responsibilities

Serve as the strategic commercial partner to GTM teams, transforming implementation into a competitive advantage that accelerates deal closure and time-to-revenue; Architect scalable implementation frameworks that operationalize complex tax and compliance requirements, removing friction for sales and enhancing the client experience from day one; Lead complex client migrations and platform transitions, managing risk with high-fidelity operational rigor while proactively advocating for client-centric, commercially viable solutions; Define and execute the operational playbook for new growth channels, ensuring that compliance and regulatory standards act as a foundation for, rather than a barrier to, commercial velocity; Collaborate with Product and Sales leadership to turn operational complexity into clear, compelling value propositions, fostering client trust through predictable, high-accuracy transitions; Establish and enforce payroll operational governance across all implementation activities, in compliance with applicable regulatory requirements, including multi-state tax registrations, wage and hour requirements, FLSA requirements, and accurate payroll tax setup; Ensure accurate quarter and year-end processing including federal, state, and local tax reconciliations, W-2/1099 issuance, and audit-ready documentation; Design and maintain internal controls, audit procedures, and compliance documentation to minimize payroll errors, tax penalties, and regulatory violations; Partner with Compliance, Legal, and Tax to incorporate relevant federal, state, and local tax law changes into implementation processes; provide operational guidance to internal teams and serve as escalation point for complex payroll and tax-related matters; Address payroll tax inquiries and issues; collaborate with federal, state, and local tax authorities on tax notices and audit responses; Maintain a high level of data integrity for the Customer Success team by auditing clients' payroll data—including tax filings and imported payroll history from a client's previous provider—and ensuring Justworks is set up to file with the appropriate tax agencies; Lead operational governance framework development for TPA integrations and support compliance attestations and third-party risk management; Establish control matrices, documentation requirements, data validation procedures, and reconciliation controls; Partner with Compliance, Legal, and Risk teams on regulatory audits, attestations, and internal controls testing; manage associated operational corrective action plans and remediation; Support SOX/SOC 2 compliance initiatives and coordinate audit preparation and documentation; Lead and develop a high-performing, efficient payroll and compliance team; provide guidance, mentorship, and development to specialists and tax professionals; Attract top talent and build diverse teams capable of scaling; establish career development paths and continuous learning culture; Architect scalable processes and leverage technology/automation to handle volume without proportional headcount increases; Continuously evaluate and implement best practices; drive operational excellence through process streamlining, efficiency improvements, and innovation

Requirements

10+ years in payroll tax operations within PEO, ASO, or HR outsourcing environments; Expertise in multi-state tax compliance and client implementation operating models; Deep knowledge of TPA environments, vendor management, and compliance governance; Advanced Excel skills for complex data analysis and electronic tax filing proficiency; 7+ years of management experience, including 4+ years leading managers and teams of 5+; Proven ability to motivate, mentor, and develop diverse payroll and tax professionals; Strong client-facing skills with the ability to simplify complex regulatory matters; Bachelor’s degree in Accounting, HR, or Business (or equivalent experience)

Nice to have

CPP, CPA, or relevant payroll/tax certification strongly preferred

Benefits

great benefits; wellness program offerings; company retreats; ability to interact with and learn from leaders in the startup community