Director, Payroll Business Lead (DRI)

The Director, Payroll Business Lead is the Directly Responsible Individual (DRI) for the successful execution of the Payroll FY27 plan. You own the outcome — the bookings, the LTV, the margin trajectory, and the decisions that get us there.

You are a business owner first with strong General Management instincts. You treat Payroll as a P&L and a growth engine to run, not a function to coordinate. You are comfortable setting commercial strategy, informing the pricing decisions, and getting into the operational detail when the numbers are off track. You thrive in creation environments where product, pricing, and operating models are still taking shape, and you bring the structure, discipline, and financial rigor to scale the business profitably. You lead through ownership and influence rather than headcount, and you are trusted to run a business line and deliver its results.

You will report to the leader with oversight of our Acquisition System and Payroll business line, in the CMO organization. 

• Owning the Payroll Business and Financial Outcomes

  • Serve as DRI for the Payroll annual plan, accountable for its revenue, expansion, and margin commitments.
  • Orient the business around LTV, ARPC growth, and Payroll's contribution to platform-level customer and revenue growth.
  • Own the commercial strategy to scale customer acquisition  against the defined ICP, across both marketing-driven inbound and partnerships.
  • Own the monetization, bundling, and expansion agenda, including pricing, packaging, and new paid services.
  • Own the path to gross-margin break-even on cost-to-serve without compromising service quality.
  • Make the trade-off and prioritization calls the plan requires, and answer for the results.
  
  
• Driving Cross-Functional Execution
  • Direct execution of Payroll initiatives across Marketing, Technology, Operations, Product, Finance, Revenue and Risk & Insurance.
  • Keep roadmap priorities informed by partner-facing GTM and ICP signals, with clear lead time for teams to plan against.
  • Own the outcomes of the Payroll-to-PEO expansion pathway, from surfacing upgrade-ready customers to reducing migration friction.
  • Land pricing and packaging into the financial plan, with new add-ons integrated naturally into acquisition and expansion.
  • Identify gaps and risks in execution and drive resolution through collaboration and influence.
  • Build and maintain cross-functional operating systems to keep partners and stakeholders aligned.
    
• Business Storytelling and Structure
  • Represent Payroll in platform-level and leadership forums, grounding discussions in data, financial impact, and customer outcomes.
  • Bring structure to ambiguous problems and produce the artifacts that keep the organization aligned to the plan.
  • Reinforce a culture of ownership and accountability as the business matures.

Success looks like: Our Payroll business delivers its fiscal year commitments, runs on a reproducible growth motion, and operates as an owned, accountable business line.

• Ownership and Accountability — operating as the DRI: full accountability for outcomes, not effort.
• Business Insight — applying knowledge of the business, unit economics, and marketplace to advance commercial goals.
• Strategic Mindset — anticipating trends and articulating credible visions that create sustainable value.
• Drives Results — achieving results even under tough conditions and with no direct functional reporting lines; owning the number and the path to it by influencing throughout our matrixed organization.
• Financial and Commercial Acumen — making sound pricing, monetization, and investment trade-offs.
• Plans and Aligns — breaking objectives into actions and aligning teams around shared commitments.
• Executive Communication and Influence — driving alignment across functions and leadership without direct authority.

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.”

• Minimum 10 years of professional experience, with a track record of owning a business line, P&L, or comparable end-to-end commercial outcome.
• Demonstrated experience as a co-founder, General Manager, DRI or business owner — personally accountable for revenue, margin, or growth, not solely program coordination.
• Experience in SaaS, fintech, B2B services, or other regulated or operationally complex environments preferred.
• High business and financial acumen; fluency with P&L, unit economics, LTV/CAC, ARPC, and pricing and packaging.
• Proven ability to set commercial strategy and drive it through execution across functions.
• Strong analytical skills and familiarity with data tools (e.g., Excel, SQL).
• Record of leading cross-functional initiatives to measurable outcomes through influence rather than direct authority.
• Ability to succeed in an entrepreneurial, ambiguous environment and bring structure without slowing innovation.
• Executive presence sufficient to represent a business line in leadership forums.
• Strong sense of ownership and a focus on results and outcomes, not just process.
• Unquestionable professional ethics, strong judgment, and commitment to excellence.

The base wage range for this position based in our New York City Office is targeted at $240,000.00 - $263,500.00 per year.

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