Director, Payroll & Tax Implementation

United States Digital Space LLC; New York (NY); On-site; USD 150,000 - 210,000; Full time

Job summary

United States Digital Space LLC in New York seeks a Director of Payroll and Tax Implementation to lead our payroll and tax operations at scale. You will align regulatory compliance with commercial growth, designing governance and rollout plans for multi-state payroll.

You will partner with Compliance, Legal, and Tax, build scalable processes, and mentor a growing team to deliver accurate, timely results while enabling GTM velocity.

Qualifications

• Extensive experience in payroll and tax compliance governance.
• Proven leadership of large, multi-state payroll programs.

Responsibilities

• Lead operational governance for payroll and tax implementations.
• Architect scalable processes to support growth and compliance.
• Partner with Compliance, Legal, and Risk on regulatory changes.
• Develop and mentor a high-performing payroll team.
• Drive cross-functional alignment with Sales, Product, and Finance.

Job description

Who We Are

At the company, you’ll enjoy a welcoming and casual environment, great benefits, wellness program offerings, company retreats, and the ability to interact with and learn from leaders in the startup community. We work hard and care about our most prized asset - our people.

We’re helping businesses get off the ground by enabling them to focus on running their business. We solve HR issues. We’re data-driven and never stop iterating. If you’d like to work in a supportive, entrepreneurial environment, are interested in building something meaningful and having fun while doing it, we’d love to hear from you.

We're united by shared goals and shared motivations at the company. These are best summed up in our company values, which are reflected in our product and in our team.

Our Values

If this sounds like you, you’ll fit right in.

Who You Are

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.

Your Success ProfileImplementation 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 the company 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 Payroll and Tax Implementation, 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.

QualificationsOperational & Industry Expertise (PEO/ASO)

• 10+ years