HealthJoy
HealthJoy5d ago
New
$145,000 – $160,000/yr

Principal Actuary

United StatesUnited StatesRemotelead
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Requirements Summary

You have built savings or value studies and been f

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OtherActuary

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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 and largely underutilized by most people. That’s why HealthJoy was built with one vision: to remove the complexity from being healthy and well. We do that by guiding employees to affordable, high-quality healthcare, consolidating our clients’ health and wellness strategies into the HealthJoy Benefits Operating System - a simple, unified digital experience. The result: healthier employees and a healthier bottom line.

HealthJoy is at the forefront of using AI to transform the healthcare benefits industry. We're building intelligent platforms that use predictive analytics, natural language processing, and machine learning to guide employees to affordable, high-quality care. Our team is passionate about creating a more equitable and understandable benefits experience, while saving our clients time and money.

HealthJoy has garnered workplace awards from Inc.'s Fastest Growing Startups and Built In Chicago's Best Places to Work while growing globally to over 300 team members. We're continuing down the path of high growth and high impact — and this role is one of the most consequential bets we're making.

We are hiring a Principal Actuary to lead the actuarial side of how we design, price, and measure our products. You will report directly to the CFO and work closely with our executive, product, and data science teams. We already have strong data science and analytics capabilities; this role adds dedicated actuarial leadership to that work.

Some of what this role will work on is not public yet. We will share the specifics during the interview process. What we can say here is that the work sits at the center of where the company is headed, and the math has to be good enough to convince skeptical outside reviewers.

Own how we measure value. Build and defend the methodology we use to measure the financial results of our programs. It needs to hold up when an outside actuary, a benefits consultant, or an underwriter takes it apart.

Build risk and forecasting models. Partner with our data science team on models that forecast medical cost and utilization for self-funded populations, and own the actuarial assumptions behind them.

Design Health Reimbursement Arrangements. Design employer-funded HRAs and incentive programs, including funding levels, rollover rules, reimbursement and substantiation, keeping members HSA-eligible, and staying compliant with IRS rules, including Section 105(h) nondiscrimination testing.

Support pricing. Help structure our pricing, including performance guarantees, reconciliation mechanics, and the reserves behind them.

Support plan design. Work with employers, brokers, consultants, TPAs, and stop-loss partners on plan design questions across our book of business.

Stand behind the numbers. You will sit across the table from actuaries at consulting firms and underwriting partners. You will explain our methods and answer the hard questions.

  •     ASA or FSA (MAAA preferred) with at least 7+ years of health actuarial experience, ideally on commercial or employer-sponsored plans
  •     A strong understanding of self-funded plan economics, including stop-loss, lasering, and claims forecasting
  •     Hands-on experience designing and modeling employer-funded Health Reimbursement Arrangements, including how they fit with the medical plan, HSA compatibility, ERISA and COBRA requirements, and IRS compliance
  •     Experience forecasting HRA utilization, setting rollover and forfeiture assumptions, and pricing incentive dollars based on how members actually respond
  •     Experience building or reviewing program savings studies, and honest opinions about where the common methods fall short
  •     Strong SQL skills; Python or R is a plus
  •     A track record of standing behind numbers that were reviewed by outside parties
  •     You have built savings or value studies and been frustrated by what you could not prove
  •     You would rather work at a company that sets its measurement standards up front than one that leads with a flashy ROI slide
  •     You want broad ownership and visibility rather than a narrow slice of a large actuarial department
  •     You want a direct line to the executive team and a real say in product, pricing, and partner decisions

Job band - 90 - this is a senior leadership role, reporting directly to the CFO

Base salary of $220,000 to $270,000, plus an annual bonus target and equity. The final offer depends on experience and credentials.

Certain roles are eligible for additional cash incentives such as commission, annual bonus targets, overtime pay or other variable incentives.

HealthJoy maintains a comprehensive strategy to determine rewarding and competitive packages for individual compensation for new hires, internal promotions and internal job changes. This strategy is based on several factors unique to each individual, including: 1) the skills, experience and qualifications of the individual; 2) the responsibilities and demands of the role; 3) analysis of external market data; and 4) company budget and financial performance.

Location & Eligibility

Where is the job
United States
Remote within one country
Who can apply
US

Listing Details

Posted
August 12, 2026
First seen
August 12, 2026
Last seen
August 17, 2026

Posting Health

Days active
0
Repost count
0
Trust Level
80%
Scored at
August 12, 2026

Signal breakdown

freshnesssource trustcontent trustemployer trust
HealthJoy
HealthJoy
greenhouse
Employees
350
Founded
2014
View company profile
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HealthJoyPrincipal Actuary$145k–$160k