Head of Finance & Strategic Performance

Overview

The organization is seeking a Head of Finance & Strategic Performance to join the executive leadership team. This is a full-time, salaried role reporting directly to the Co-CEOs.

This position owns the full finance function across the group, ensuring strategic finance leadership while keeping reporting accurate, compliant, and efficient. Travel is required for executive and quarterly planning sessions.

Responsibilities

• Serve as the Co-CEOs’ trusted financial adviser and a full member of the executive team in strategic planning, quarterly goal setting, and major decisions.
• Lead capital allocation and strategic finance by:
  • Evaluating competing investments and recommending where resources should go using models that compare growth scenarios, reinvestment options, risks, and expected returns.
  • Assessing whether current profitability reflects optimal performance or missed opportunities to reinvest.
  • Cutting spending that fails to earn its keep and supporting investments with strong economic potential.
  • Partnering with business leaders to evaluate revenue growth, pricing, monetization, and business model innovation using financial and customer insights.
• Make business economics visible by:
  • Building activity-level cost models for major functions.
  • Establishing unit economics across acquisition, retention, customer support, trust and safety, and AI operations.
  • Comparing internal teams, outsourced providers, technology investments, and alternative operating models on cost and outcome.
  • Maintaining a consolidated executive finance dashboard across the group.
• Hold every investment to measurable ROI by:
  • Partnering with project owners to build investment cases with clear costs, expected benefits, assumptions, and success metrics before commitments.
  • Tracking performance against the investment case, flagging variances early, and recommending whether to expand, modify, or stop.
  • Measuring realized returns (including separating true incremental gains from results that would have happened anyway).
  • Setting one company-wide method for measuring and validating business value and reconciling savings across departments, including AI automation savings.
• Turn budgeting into a strategic tool by:
  • Leading annual planning aligned with company strategy and OKRs using driver-based models.
  • Building initiative-based budgets funded by expected returns.
  • Running rolling forecasts and scenarios.
  • Testing assumptions with department leaders, weighing trade-offs, and improving forecast accuracy.
• Partner on organization, incentives, and gain share by:
  • Working with the Head of People & Organizational Effectiveness on organizational structure, workforce planning, hiring investments, compensation, and productivity.
  • Owning the gain share program economics—how value is measured, validated, and funded.
  • Bringing financial rigor to people decisions while supporting operating ownership of other leaders.
• Lead a lean, AI-enabled finance function by owning and operating:
  • Performance and integrity of accounting, reporting, payroll, cash and liquidity, tax, regulatory compliance, controls, and risk.
  • Finance across the international group, including intercompany agreements and settlements, transfer pricing documentation, and consolidated reporting.
  • Ongoing partnership with outside tax and corporate structure advisors as the structure evolves.
  • Management of internal finance staff and outside accounting, tax, and financial service partners, holding all to clear standards.
  • Delegating routine operations to keep focus on strategy, performance, and growth.
• Manage quarterly OKRs for the finance function, including leading and lagging KPIs, and run the work in Confluence, Jira, and Monday.

Requirements (What You Must Bring)

• Proven value creation with a track record of financial insight and investment decisions that produced measurable business value.
• Direct experience driving profitable growth through financial decisions, including (for example) scaling a profitable business, improving capital allocation, leading strategic reinvestment, raising operational efficiency, improving unit economics, or building finance processes that materially improved performance.
• Strategic finance and FP&A depth with eight or more years in strategic finance, FP&A, or corporate finance, including leadership of a finance team or function.
• Operational understanding that connects accounting records and operating data to decisions leaders can act on.
• Finance operations leadership, including experience overseeing accounting, reporting, payroll, tax, and controls through internal teams, outside partners, or both.
• Executive partnership experience shaping strategy alongside senior leaders and founders, influencing decisions through sound judgment and compelling analysis.
• Enterprise-wide perspective to evaluate trade-offs across functions and optimize outcomes for the business as a whole.
• Data and systems fluency, including advanced modeling and comfort working directly in data and BI tools, with experience using modern finance technology.
• Daily use of AI tools (the role specifically notes Claude, Claude Code, Cowork, or comparable tools) and an understanding of how automation and AI can run a leaner, sharper finance function.

Preferred Qualifications (Nice to Have)

• Experience running finance for an international, multi-entity group, including intercompany agreements, transfer pricing, and consolidated reporting.
• Subscription, marketplace, consumer technology, or digital platform experience.
• Experience helping an established, profitable company accelerate growth.
• Experience working directly with founders or entrepreneurial CEOs.
• Experience building or transforming an FP&A function, including activity-based costing and operational performance measurement.
• Experience designing performance measurement and incentive systems tied to value creation.
• MBA, CPA, or CFA.

Compensation & Benefits

• Base salary: $175,000 to $225,000 (based on demonstrated capability)
• Full-time, salaried
• Gain share tied to demonstrated repeatable value; as a member of the executive team, participation is tied to the growth the role helps create
• Benefits:
  • 99% coverage of medical base plan, dental, and vision
  • 50% 401(k) match up to 6%
  • Flexible Spending Account
  • Flexible paid time off

Location

Remote, anywhere in the US.

Travel

Required for executive and quarterly planning sessions.

Hiring Process

• Recruiter screen: strongest example of value creation (with numbers) plus logistics
• Finance deep dive: working session on modeling, unit economics, and how accounting, controls, and outside partners are run
• Case exercise: fictionalized customer support and moderation cost data plus proposed investment in AI automation; evaluate unit costs, expected returns, implementation risk, and service quality, and recommend whether to proceed
• Executive partner round: meetings with the Head of People & Organizational Effectiveness and other leaders
• Co-CEO round: pitch-style discussion; study the business, ask questions, and share where the organization should invest next and how you would shape the finance function in your first 90 days
• References: including a CEO or founder you advised and a former direct report

Equal Opportunity Employer

The organization is an equal opportunity employer committed to diversity and inclusion in the workplace. It prohibits discrimination of any kind and encourages qualified candidates to apply regardless of race, color, sex, religion, sexual orientation, national origin, disability, genetic information, or any other protected characteristics as outlined by federal, state, or local laws. Hiring decisions are based solely on qualifications, merit, and business needs. Offers are contingent upon completion of a full background and reference check.