Lead Financial Analyst

Come for the mission. Stay for the experience. Let’s keep things simple: we are an unbelievably talented, hard-working, and compassionate team driving towards a mission that impacts every single one of us - even you! Healthcare benefits are complex, underutilized and a mystery for most users. We’re removing that complexity. Now more than ever, employers are adding value to their employees’ benefits like telemedicine and mental health services. HealthJoy’s industry-changing tech platform consolidates those benefits into a simplified benefits experience, saving users time and money. HealthJoy has garnered workplace awards for Inc. 's Fastest Growing Startups and Built In Chicago’s Best Places to Work while growing globally to nearly 400 team members. We’re continuing down the path of high growth and high impact, and this role is a key member of the Finance Team making that happen. Your impact. This is not a "support the team" role. You will be the second seat in HealthJoy's Strategic Finance function, working directly with our VP of Finance & Revenue Strategy to own the financial models, analyses, and recommendations that drive how HealthJoy plans, prices, and grows. You'll also be the analytical partner for our GTM motion (covering sales and marketing performance, pipeline economics, and channel efficiency) and the backup on pricing and deal desk, triaging non-standard requests so decisions can happen faster. We're a remote-first startup environment: fast-paced, ambiguous, and often chaotic. You'll thrive here if you bring strong finance fundamentals, high agency, building appetite, and a hunger to own outcomes, not just tasks. Desired Outcomes: Own HealthJoy's Core Financial Models End-to-End: Take full ownership of the operating model, long-range plan, and the financial backbone of board reporting. You build, maintain, defend, and evolve; leadership reviews. Set the modeling standards the rest of the organization relies on. Drive Strategic Finance Analyses That Move the Business: Lead the analytical work behind unit economics, segment profitability, pricing strategy, packaging, and growth analysis. Translate complex data into clear recommendations that executives can act on. Sharpen GTM Performance Through Analytical Partnership with RevOps: Own the analytical layer for sales and marketing performance — pipeline economics, rep productivity, CAC efficiency, funnel diagnostics, channel ROI, comp plan economics. This is a meaningful portion of the role, not a side project; you'll partner closely with our GTM Systems lead to ensure the data is right and the insights are actionable. Partner on the FP&A Operating Rhythm: Contribute to the monthly close partnership, budget vs. actuals reporting, headcount tracking, and the board financial package, working alongside other Finance team members who own pieces of this work. Serve as a finance partner for one or more departments, running their budget and headcount planning independently. Triage and Structure Pricing and Deal Desk Work: Tee up non-standard deal requests with clean analysis and a recommended structure so decisions can happen faster. Serve as backup for routine pricing exceptions and escalate the hard ones with context. Build AI-Native Finance Workflows: Be hands-on in shaping our AI-native finance function — designing workflows in Claude and other platforms, automating analysis and reporting, and creating finance tooling that didn't exist before. You should bring building appetite and aptitude; we'll build a lot together. Key Responsibilities: Own the operating model and long-range plan end-to-end Lead annual budgeting and quarterly re-forecasting cycles Build models for unit economics, cohort profitability, LTV/CAC, segment P&Ls, and pricing scenarios Run RevOps analytics: pipeline, rep productivity, channel ROI, comp plan economics Contribute to monthly close, BvA reporting, and the board package alongside other Finance team members Triage pricing and deal desk requests;