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.

Responsibilities

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; 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; 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

Requirements

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; 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; 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

Nice to have

Experience in SaaS, fintech, B2B services, or other regulated or operationally complex environments preferred

Benefits

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