General Manager & Director, Commercial Strategy

Justworks•New York, NY

7d•$240,000 - $263,500•Hybrid

About The Position

The General Manager & Director, Commercial Strategy is the Directly Responsible Individual (DRI) for the successful execution of the Payroll FY27 plan. This role owns the outcome — the bookings, the LTV, the margin trajectory, and the decisions that get us there. The ideal candidate is a business owner first with strong General Management instincts, treating Payroll as a P&L and a growth engine to run, not a function to coordinate. They are comfortable setting commercial strategy, informing pricing decisions, and diving into operational details when numbers are off track. This role thrives in creation environments where product, pricing, and operating models are still taking shape, and brings the structure, discipline, and financial rigor to scale the business profitably. Leadership is through ownership and influence rather than headcount, and the individual is trusted to run a business line and deliver its results. This role reports to the leader with oversight of the Acquisition System and Payroll business line, within the CMO organization.

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.

Nice To Haves

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

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.