Head of Finance & Strategic

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

and its international group of companies

Remote, anywhere in the US

Co-CEOs

The full finance function across the group: strategic finance, FP&A, accounting, consolidated reporting, intercompany, controls, payroll, tax, treasury, and outside finance partners

$175,000 to $225,000 base

Required for executive and quarterly planning sessions

is the world's largest premium dating platform, founded and led by an MIT alumnus. Together with our news publication , 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.

• 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?

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…