Lead Financial Analyst

HealthJoy

2d•$115,000 - $145,000•Remote

About The Position

HealthJoy is a rapidly growing, remote-first startup focused on simplifying healthcare benefits through an industry-changing tech platform. We are seeking a talented and driven Lead Financial Analyst to join our Strategic Finance function. This role is crucial in driving the company's financial planning, pricing, and growth strategies. You will work directly with the VP of Finance & Revenue Strategy, owning financial models, analyses, and recommendations. The position also involves partnering with the Go-To-Market (GTM) team on sales and marketing performance, pipeline economics, and channel efficiency, as well as supporting pricing and deal desk operations. We are looking for individuals with strong finance fundamentals, high agency, a desire to build, and a hunger to own outcomes in a fast-paced, ambiguous, and sometimes chaotic startup environment.

Requirements

Minimum of 7 years of progressive experience in FP&A, Strategic Finance, investment banking, transaction services, private equity, or management consulting.
At least 2 years in an in-house SaaS startup or high-growth tech finance role.
Bachelor's degree in Finance, Economics, Accounting, Mathematics, or a related quantitative field.
Strong finance fundamentals: sharp commercial and financial instincts, fluency in how revenue, margin, and cash work together, structured problem-solving on ambiguous business questions, and analytical rigor.
Advanced financial modeling and SaaS fluency: Power user of Excel/Sheets for scenarios, sensitivities, cohort and unit economics modeling, multi-sheet model design.
Deep understanding of ARR, NDR, GDR, CAC, LTV, and payback, and how they connect to GAAP.
High agency and ambiguity tolerance: Takes ambiguous prompts and returns structured approaches, not requests for direction. Owns analyses end-to-end with a recommendation.
Thrives in a remote-first startup environment that is fast-paced with constantly shifting priorities.
BI fundamentals: Comfortable with structured data and modern BI tools. Familiarity with underlying concepts matters more than fluency in any specific tool.
AI building experience and appetite: Experience building with AI (e.g., workflows in Claude, custom GPTs, prompt-engineered analysis, automations).
GTM/RevOps and deal-level comfort: Prior exposure to sales and marketing analytics including pipeline, comp plan economics, channel ROI, or similar. Comfortable structuring a deal scenario and teeing up a recommendation.
Executive presence and strong written communication: Comfortable presenting to senior leadership. Work product reads like a recommendation, not a data dump.

Nice To Haves

Healthcare or insurance industry experience.
Familiarity with NetSuite, Salesforce, or modern planning tools.

Responsibilities

Own HealthJoy's Core Financial Models End-to-End, including the operating model, long-range plan, and financial backbone of board reporting.
Set modeling standards for the organization.
Drive Strategic Finance Analyses including unit economics, segment profitability, pricing strategy, packaging, and growth analysis.
Translate complex data into clear recommendations for executives.
Own the analytical layer for sales and marketing performance, including pipeline economics, rep productivity, CAC efficiency, funnel diagnostics, channel ROI, and comp plan economics.
Partner closely with the GTM Systems lead to ensure data accuracy and actionable insights.
Contribute to the monthly close, budget vs. actuals reporting, headcount tracking, and the board financial package.
Serve as a finance partner for one or more departments, independently running their budget and headcount planning.
Triage and structure pricing and deal desk work, preparing clean analysis and recommended structures for non-standard deal requests.
Serve as backup for routine pricing exceptions.
Be hands-on in shaping the AI-native finance function by designing workflows in Claude and other platforms, automating analysis and reporting, and creating new finance tooling.