Director – Implementation & Transformation

Who You Are

As Director, Implementation & Transformation in our Payroll Tax Operations division, 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, customer-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

What You Will Work On

Go-to-Market & Commercial Enablement

• Serve as strategic commercial partner to GTM teams (Sales & Customer Success), positioning implementation and operational excellence as a competitive advantage that accelerates deal closure and time-to-revenue.
• Architect scalable, customer -centric implementation frameworks that operationalize complex tax and compliance requirements while removing friction for Sales and enhancing customer experience.
• Lead complex customer migrations and platform transitions, managing risk with operational rigor while advocating for commercially viable, customer-centric solutions.
• Define and execute the operational playbook for new growth channels, ensuring compliance and regulatory standards enable rather than impede commercial velocity.

Operational Transformation & Scalability

• Design and build scalable, repeatable operational processes and frameworks that enable growth without proportional increases in headcount or complexity.
• Identify automation and efficiency opportunities across implementation, data management, and compliance workflows; drive technology-enabled solutions that reduce manual work and improve accuracy.
• Lead operational transformation initiatives—centralizing fragmented processes, implementing new systems, or restructuring workflows to serve new business models and scale.
• Establish operational metrics and KPIs that track efficiency, cost, quality, and customer impact; use data to drive continuous improvement.
• Partner with Finance, Product, and Operations teams to align operational strategy with business growth plans and ensure scalability.

Team Leadership 

• Lead and develop a high-performing payroll and operations team; attract top talent and build diverse teams capable of executing at scale.
• Provide mentorship and career development to team members; establish clear development paths and foster a continuous learning culture.
• Architect scalable team structures and leverage automation and tooling to enable your team to handle increased volume and complexity without proportional headcount growth.
• Create psychological safety and trust-based culture where team members flag problems, collaborate openly, and take ownership.

Payroll & Tax Compliance Operations

• Own accountability for payroll operational governance and regulatory compliance; establish policies, controls, and audit procedures that minimize errors, penalties, and violations.
• Lead and oversee the accuracy and integrity of payroll processing, tax filings, and compliance documentation; serve as escalation point for complex payroll, tax, and regulatory matters.
• Partner with Compliance, Legal, and Tax teams to incorporate federal, state, and local tax law changes into operational processes; guide teams on regulatory implications of business decisions.
• Establish strong relationships with tax authorities, TPAs, auditors, and external partners; manage regulatory inquiries, audit responses, and compliance attestations.

How You Will Do Your Work

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

• Strategic Thinking & Vision - 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 becomes a competitive advantage. You paint a compelling vision that motivates teams to action.
• Operational Excellence & Innovation - You identify automation and efficiency opportunities, drive process innovation, and push teams beyond comfort zones. You prioritize learning and development and inspire curiosity and continuous improvement.
• Cross-Functional Leadership - You build diverse formal and informal relationship networks inside and outside the organization. You partner effectively with Sales, Finance, Compliance, and external stakeholders. You focus on building relationships, understanding challenges, and developing solutions through active listening and open-ended questions.
• Talent Development & Culture-Building - You attract and select top diverse talent. You develop people to meet both their career goals and organizational goals through effective performance management, candid feedback, and coaching. You're known for developing future leaders and fostering psychological safety where people take ownership.

In addition, all Justworkers focus on aligning their behaviors to our core values known as COGIS. It stands for:

• Camaraderie - Day to day you can be seen working together toward a higher purpose. You like to have fun. You’re an active listener, treat people respectfully, and have a strong desire to know and help others.
• Openness - Your default is to be open. You're willing to share information, understand other perspectives, and consider new possibilities. You’re curious, ask open questions, and are receptive to thoughts and feedback from others.
• Grit - You demonstrate grit by having the courage to commit and persevere. You’re committed, earnest, and dive in to get the job done well with a positive attitude.
• Integrity - Simply put, do what you say and say what you'll do. You’re honest and forthright, have a strong moral compass, and strive to match your words with your actions while leading by example. 
• Simplicity - Be like Einstein: “Everything should be made as simple as possible, but no simpler.”

Qualifications

Core Experience

• 8+ years in operations, implementation, process leadership, or related functions with demonstrated ability to build scalable systems and drive organizational transformation.
• 7+ years of management experience, including leading and developing high-performing managers and teams.
• 3+ years in a regulated environment (payroll, tax, compliance, HR, financial services, professional services, or similar) OR demonstrated ability to rapidly master highly regulated operational domains.
• Proven ability to identify automation opportunities and drive efficiency improvements; experience implementing process improvements that meaningfully reduced costs, headcount, or cycle time.
• Experience partnering with Sales, Product, or Customer Success teams to align operations with commercial goals and business growth.
• Demonstrated ability to translate complex regulatory or operational requirements into clear, compelling narratives for non-technical audiences.

Nice-to-Have

• Familiarity with payroll, tax, or compliance operational models and regulatory environments.
• Understanding of multi-state tax compliance, TPA ecosystems, or similar governance frameworks.
• CPP, CPA, or relevant payroll/tax certification.
• Experience with SOX/SOC 2 compliance initiatives or audit preparation.

The base wage range for this position based in our Tampa Office is targeted at $155,000.00 to $200,000.00 per year.

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