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. You are comfortable navigating high-stakes environments where precision is paramount, yet you possess the agility to adapt processes for rapid business expansion. You act as a translator, decoding intricate regulatory requirements into streamlined, client-friendly workflows. By fostering deep cross-functional relationships, you ensure that the implementation journey not only secures the enterprise but also empowers our commercial teams to sell with confidence and speed.

Responsibilities

Serve as strategic commercial partner to GTM teams; Transform implementation into competitive advantage to accelerate deal closure and time-to-revenue; Architect scalable implementation frameworks that operationalize complex tax and compliance requirements; Lead complex client migrations and platform transitions; Define and execute operational playbook for new growth channels; Collaborate with Product and Sales leadership to turn operational complexity into value propositions; Establish and enforce payroll operational governance across implementation activities; 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; Partner with Compliance, Legal, and Tax to incorporate tax law changes; Address payroll tax inquiries and collaborate with tax authorities on notices and audits; Maintain data integrity by auditing clients' payroll data; Lead operational governance framework development for TPA integrations; Support compliance attestations and third-party risk management; Establish control matrices, documentation requirements, data validation procedures, and reconciliation controls; Support SOX/SOC 2 compliance initiatives and coordinate audit preparation; Lead and develop high-performing payroll and compliance team; Attract top talent and build diverse teams; Architect scalable processes and leverage technology/automation; Continuously evaluate and implement best practices

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

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