Director, Implementation & Transformation

Who You Are

A strategic operations leader who balances deep regulatory rigor with a commercial, growth-oriented mindset in our Payroll Tax Operations division. 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.

Your Success Profile

Implementation Strategy & Commercial Enablement

• 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.

Payroll & Tax Compliance Operations

• 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.

TPA Integration Governance & Operational Controls

• 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.

Team Leadership & Scaling

• 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.

How You Will Do Your Work

As the Director of Implementation and Transformation, how you achieve results is as important as the results themselves. Your success is anchored in these core competencies and values:

• Strategic Mindset: You see ahead to future possibilities and translate them into breakthrough strategies. You balance deep operational expertise with the ability to think strategically about how implementation can become a competitive advantage.
• Drives Vision & Purpose: You paint a compelling picture of the vision and strategy that motivates others to action. You command a room, share challenges and successes through storytelling, and inspire your team to pursue excellence.
• Build Networks: You effectively build diverse formal and informal relationship networks inside and outside the organization. You partner closely with Sales, Finance, Compliance, and external stakeholders (tax authorities, TPAs, auditors).
• Attracts Top Talent: You attract and select the best diverse talent to meet current and future business needs. You are known for developing future leaders and building high-performing teams.
• Cultivates Innovation: You inspire creativity and curiosity, push beyond comfort zones, and prioritize learning and development for yourself and your team. You identify automation opportunities and drive process innovation.
• Develops Talent: You develop people to meet both their career goals and the organization's goals through effective performance management, candid feedback, and coaching conversations.
• Consultative Approach: You focus on building relationships, understanding challenges, and developing solutions through active listening and open-ended questions. You partner with clients and internal stakeholders to address their needs.

Qualifications

Operational & Industry Expertise (PEO/ASO)

• 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.

Leadership & Management

• 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.

Education & Credentials

• Bachelor’s degree in Accounting, HR, or Business (or equivalent experience).
• CPP, CPA, or relevant payroll/tax certification strongly preferred.

The base wage range for this position based in our New York City Office is targeted at $166,000.00 to $214,000.00 per year.

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