Head of Strategic Finance Jobs

HEAD OF FINANCE & STRATEGIC PERFORMANCE

Executive Leadership Team | Full-Time, Salaried | Reports to the Co-CEOs

About the Role

Seeking.com is the world's largest premium dating platform, founded and led by an MIT alumnus. Together with our news publication Standards.com, we are a lean, profitable, fully remote company of about 80 people. We operate as an international group of companies and have ambitious growth plans.

Our greatest opportunity is to invest what we have built intelligently. We need a finance leader who makes every dollar work harder: where the next million should go, which initiatives earn their keep, and what each part of the business truly costs.

You will join the executive leadership team and report directly to the Co-CEOs. You own the entire finance function and keep it accurate, compliant, and efficient, while spending most of your executive attention on strategy, capital allocation, and performance.

You will work closely with the leaders of Product, Technology, AI, Marketing, Operations, and People to understand how the business actually works, where performance can improve, and where new opportunities for growth and value creation exist. You investigate on your own initiative, challenge assumptions, and bring recommendations forward before anyone asks.

This role is for a financial executive who looks at a profitable business and immediately sees everything it could become. If your instinct is to close the month, report the numbers, and wait for questions, this is the wrong role.

Questions You Will Help Us Answer

• Are we investing enough in growth, or are we being too conservative?
• Which initiatives generate meaningful returns, and which should we reconsider?
• What does each operational activity actually cost, and how do we improve its economics?
• Where should our next million dollars go to create the greatest value?
• How should we allocate financial and human resources to reach our strategic objectives?
• Do our budgets reflect real business opportunities or last year's spending?
• How do we measure and reward the value our teams actually create?

What You Will Do

1. Lead capital allocation and strategic finance

• 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.
• Evaluate competing investments and recommend where resources should go, using models that compare growth scenarios, reinvestment options, risks, and expected returns.
• Assess whether current profitability reflects optimal performance or missed opportunities to reinvest. Cut spending that fails to earn its keep and make the case for investments with strong economic potential.
• Partner with business leaders to evaluate opportunities for revenue growth, pricing, monetization, and business model innovation, using financial and customer insights to inform strategic decisions.
• You hold recommendation authority, and the Co-CEOs hold final approval on major investments. Your authority expands as your judgment proves out. You are accountable for the rigor of every recommendation, its assumptions, and its measured outcome.

2. Make the economics of the business visible

• Build activity-level cost models for every major function: the fully loaded cost of a moderated upload, a resolved support ticket, an acquired member, a shipped feature.
• Establish unit economics across acquisition, retention, customer support, trust and safety, and AI operations, tied to operating measures of productivity, service levels, and quality.
• Compare internal teams, outsourced providers, technology investments, and alternative operating models on cost and outcome.
• Keep one consolidated executive finance dashboard across the group that leaders use to understand costs, performance, and opportunity.

3. Hold every investment to measurable ROI

• Partner with project owners to build investment cases with clear costs, expected benefits, assumptions, and success metrics before money is committed.
• Track performance against the case through execution, flag variances early, and recommend whether to expand, modify, or stop.
• Measure realized returns in revenue, cost savings, productivity, and long-term value, and separate true incremental gains from results that would have happened anyway.
• Set one company-wide method for measuring and validating business value, and reconcile the savings every department claims, including savings from AI automation.

4. Turn budgeting into a strategic tool

• Lead annual planning aligned with company strategy and OKRs, using driver-based models that connect operating activity to financial outcomes.
• Build initiative-based budgets that fund strategic priorities according to expected returns.
• Run rolling forecasts and scenarios that adapt as conditions change.
• Work with department leaders to test assumptions, weigh trade-offs, and improve forecast accuracy.

5. Partner on organization, incentives, and gain share

• Work closely with our Head of People & Organizational Effectiveness on organizational structure, workforce planning, hiring investments, compensation, and productivity.
• Own the economics of our gain share program: how value is measured, validated, and funded, so rewards track measurable, sustainable value creation.
• Bring financial rigor to people decisions while respecting the operating ownership of other leaders. Challenge ideas constructively and build alignment around the best decision for the company.

6. Lead a lean, AI-enabled finance function

• Own the performance and integrity of accounting, reporting, payroll, cash and liquidity, tax, regulatory compliance, controls, and risk.
• Run finance across our international group of companies: intercompany agreements and settlements, transfer pricing documentation, and consolidated reporting. Partner with our outside tax and corporate structure advisors as the structure evolves, and keep it running smoothly once it is in place.
• Manage internal finance staff and outside accounting, tax, and financial service partners, and hold every one of them to clear standards.
• Build the function from the best mix of people, partners, automation, and AI. Delegate routine operations and keep your own time on strategy, performance, and growth.
• Set quarterly OKRs for the function, with leading and lagging KPIs for every Key Result. Run the work in Confluence, Jira, and Monday.

What You Must Bring

• Proven value creation. A track record of financial insight and investment decisions that produced measurable business value. You can name the recommendations you led or shaped, the reasoning behind them, and the results, with the numbers.
• You have done this before. Direct experience driving profitable growth through financial decisions: scaling a profitable business, improving capital allocation, leading strategic reinvestment, raising operational efficiency, improving unit economics, or building finance processes that materially improved performance. The impact counts more than the title you held.
• Strategic finance and FP&A depth. Eight or more years in strategic finance, FP&A, or corporate finance, including leadership of a finance team or function. Deep skill in modeling, forecasting, budgeting, investment analysis, unit economics, and capital allocation.
• Operational understanding. You look past the financial statements to the activities, processes, and drivers that produce the results, and you turn accounting records and operating data into decisions leaders can act on.
• Finance operations leadership. Experience overseeing accounting, reporting, payroll, tax, and controls through internal teams, outside partners, or both.
• Executive partnership. You have shaped strategy alongside senior leaders and founders, influencing decisions through sound judgment and compelling analysis, and you tell the Co-CEOs plainly when the evidence points another way.
• Enterprise-wide perspective. You understand how strategy, operations, technology, talent, and financial performance connect. You can evaluate trade-offs across functions and help leaders make decisions that optimize outcomes for the business as a whole.
• Data and systems fluency. Advanced modeling, comfort working directly in data and BI tools, and experience with modern finance technology.
• Daily use of AI. You use Claude, Claude Code, Cowork, or comparable tools in your own analysis, and you see how automation and AI can run a leaner, sharper finance function. If someone has to explain to you why AI matters, this role is not for you.

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.
• An MBA, CPA, or CFA.

Who Thrives Here

• You think like an owner. You treat company resources as opportunities to create value.
• You are relentlessly curious. When you see an expense, you want to know what we are buying, why, and whether a better option exists.
• You are commercially minded. You know financial success comes from putting resources where the returns are greatest.
• You are intellectually independent. You challenge any executive, including the Co-CEOs, when the evidence calls for it.
• You are accountable. You stand behind your recommendations, measure their outcomes, own your misses, and sharpen your judgment.
• You are a builder. You create better systems, processes, and capabilities, and you leave every function stronger than you found it.

What Success Looks Like in Twelve Months

• Leadership has a clear, actionable view of major operating costs and unit economics across the business.
• Every material initiative has measurable objectives, stated assumptions, and ongoing tracking against its investment case.
• Capital flows increasingly toward the opportunities with the greatest long-term value.
• Budgets and forecasts run on operating drivers and tie directly to strategy and OKRs.
• You have independently brought forward and quantified meaningful opportunities for growth, efficiency, and reinvestment.
• Accounting, reporting, compliance, and finance operations run accurately and efficiently.
• The Co-CEOs make better decisions because of your work.

We will measure your contribution by how well you help the company understand, allocate, and grow its resources.

Compensation

• $175,000 to $225,000 base, based on demonstrated capability. Full-time, salaried.
• Gain share tied to demonstrated repeatable value. As a member of the executive team, you share in the growth you help create.
• 99% coverage of our medical base plan, dental, and vision. 50% 401(k) match up to 6%. Flexible Spending Account and flexible paid time off.

How We Hire

• Recruiter screen: your strongest example of value you created, with the numbers, plus logistics.
• Finance deep dive: a working session on modeling, unit economics, and how you have run accounting, controls, and outside partners.
• Case exercise: we give you a fictionalized version of our customer support and moderation cost data alongside a proposed investment in AI automation. Evaluate current unit costs, expected returns, implementation risk, and service quality, then recommend whether to proceed. The strongest candidates find the questions that matter, challenge weak assumptions, and land on a clear recommendation.
• Executive partner round: meet our Head of People & Organizational Effectiveness and other leaders you will work alongside.
• Co-CEO round: treat it as a pitch. Study the business, ask sharp questions, and bring your view of where Seeking 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

Reflex Media is an equal opportunity employer committed to diversity and inclusion in the workplace. We strictly prohibit discrimination of any kind. Candidates are encouraged to apply for qualified positions 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. Reflex Media's hiring decisions are based solely on qualifications, merit, and the needs of the company. All offers of employment are contingent upon the completion of a full background and reference check.

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