Lead Financial Analyst, HealthJoy
$115-145k
Excel
Salesforce
NetSuite
ChatGPT
Senior and Expert level
Remote from US
Health benefits platform for employers
Be an early applicant
Health benefits platform for employers
201-500 employees
HealthcareB2BEnterpriseHR
Be an early applicant
$115-145k
Excel
Salesforce
NetSuite
ChatGPT
Senior and Expert level
Remote from US
201-500 employees
HealthcareB2BEnterpriseHR
Company mission
To simplify the healthcare experience by removing the complexity from being healthy and well.
Role
Who you are
- Minimum of 7 years of progressive experience in FP&A, Strategic Finance, investment banking, transaction services, private equity, or management consulting, with 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 the analytical rigor expected of top consulting, banking, or strategic finance environments
- 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, not just the math. Thrives in a remote-first startup environment that is fast-paced with constantly shifting priorities. Not everyone thrives here; you should honestly assess if this culture descriptor matches your own work energy!
- 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. You've started building with AI, and not just used ChatGPT for emails. Concrete examples are great (workflows in Claude, custom GPTs, prompt-engineered analysis, automations that replaced manual finance work), but what matters most is appetite and aptitude. You want to build, you learn fast, and you'll ship things alongside the rest of the team
- 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. Direct deal desk experience is a plus; judgment and analytical structure matter more than reps
- Executive presence and strong written communication. Comfortable presenting to senior leadership. Your work product reads like a recommendation, not a data dump
- Healthcare or insurance industry experience is a plus, not required
- Familiarity with NetSuite, Salesforce, or modern planning tools is a plus
What the job involves
- 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; serve as backup on routine pricing exceptions
- Ship AI-native finance workflows that replace manual work
- Partner with one or more departments on budget and headcount
- Collaborate with Accounting and Finance team members on reporting cadence
Our take
Although shopping around for a car or mortgage is standard practice, when it comes to medical procedures, people often take what they are given. HealthJoy is a company that helps employees shop around for the most cost-effective healthcare options, then rewards these employees when they take the lower-cost option.
The HealthJoy benefits experience platform combines a chatbot with artificial intelligence along with human input to settle on the most affordable available treatment for employee. Savings are then shared with the employee via a savings account or gift card. HealthJoy focuses on providing its services to larger companies, with tens of thousands of users, but has expressed intentions to work with small and medium-sized businesses in the future.
As healthcare costs continue to rise, HealthJoy is ready for continued success by helping employers manage expenses and improve employee care. With a strong track record and strategic partnerships, the company is set to deliver lasting value as demand for affordable, high-quality care grows.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
Top investors
7% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Oct 2022
$60m
SERIES D
Feb 2020
$30m
SERIES C
Total funding: $108.5m
Company benefits
- Remote Work: Being a remote-first company, we give new employees a remote work stipend to ensure you can work comfortably from home
- Health & Wellness: We offer healthcare benefits including medical, dental, vision, therapy, HSA contribution match, EAP, telemedicine, virtual exercise therapy, and disability
- Company Events: We provide our employees with virtual-lunch-and-learns, virtual coffee chats, happy hours, and quarterly team activities
- Financial Wellness: We offer equity with our Stock Option Distribution Policy, 401k match, and an employee referral bonus program
- Recharge: HealthJoy provides employees the freedom they need to balance the responsibilities of both their work and home lives. We offer flexible PTO, paid holidays, parental leave, and more
Company HQ
River North, Chicago, IL
Leadership
Justin Holland
(Co-Founder & CEO)Having studied at MIT, they co-founded FreeCause in 2006 and OpenInstall in January 2011. They then spent 1 year as VP Platform at AVG before founding HealthJoy as CEO in March 2014.
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