Principal Actuary

This role is preferred in Tampa, FL, with hybrid flexibility, but remote is an option for the right person.

Come for the mission. Stay for the innovation.

Let’s keep things simple: we’re a talented, hard-working, and compassionate team driving towards a mission that impacts every single one of us. Our path to success is paved with our proprietary technology, demanding team members who are naturally AI-forward and data-driven to accelerate our impact.

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.

With over $100M in fundraising to date, and the successful closing of our recent Series D, HealthJoy has garnered workplace awards for Inc.’s Fastest Growing Startups and Built In Chicago’s Best Places to Work. 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. 

As the Controller, you will own the accounting operations function and provide leadership on all accounting initiatives. You will have responsibility for the monthly and annual close process, managing the relationships with all third party vendors and coordinating all tasks within company audits. 

You are someone who is comfortable working in a fast-paced, unstructured environment while continuing to deliver results. You will work extensively with other departments of the organization on various projects and strategic initiatives, so the willingness and ability to work cross functionally is a key part of the role.

You will own the accounting operations and due to our company’s growth, help in creating and implementing scalable process improvements. You will help define the strategic direction of the team and also have opportunities to help prepare the annual budget, build and analyze the operating model, and have a voice in key financial decisions. 

Key Responsibilities:

Drive process improvements and contribute to accounting transformation, with an eye on leveraging AI to eliminate manual work, improve speed and efficiency, and reduce potential for errors

Own the monthly and year-end close processes, including reviewing balance sheet reconciliations, performing ad-hoc analyses, trial balance reviews, international consolidation, and financial statement preparation, while adhering to tight deadlines

Ensure that financial records & reports are maintained in compliance with company policies & GAAP (accrual basis, ASC 606)

Analyze monthly operating results to ensure accurate accounting records

Oversee all payroll and billing functions

Manage client invoicing and collections

Lead the annual financial audit with independent CPA firm and 401(k) audit

Coordinate the preparation of annual tax returns with independent CPA firm including preparation of supporting workpapers

Ensure compliance with sales tax requirements in the appropriate jurisdictions

Implement, document and maintain adequate and effective internal controls, policies, and procedures

Enforce expense reimbursement policy 

Oversee the Sales commission, Bonus, Partner commission processes

Provide leadership to the accounting staff by managing, recruiting, and training employees

Provide thought leadership on emerging accounting trends

Periodically review accounting and financial management systems to ensure that systems meet business requirements and implement necessary changes

Your experience.

8+ years progressive accounting experience (minimum 2 years in public accounting strongly preferred)

Experience managing a small team of accounting professionals

Experience leveraging AI to improve accounting processes

Experience using NetSuite preferred

Strong Microsoft Excel skills (such as vlookup, sumif, pivot tables, and data analysis) and analytical skills

Ability to manage multiple projects simultaneously

A proven track record in accounting and a desire to bring best practices to a rapidly changing environment

Strong relationship management and business partner/advisory skills

Bachelor’s degree in accounting (required)

CPA required 

Total Rewards 

Job Level: 70

Base Compensation Range for Job Level: $145,000-$160,000

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. 

HealthJoy is a remote-first employer. The disclosed range estimate has not been adjusted for the applicable geographic differential associated with the location at which the position may be filled. 

At HealthJoy, it is not typical for an individual to be hired at or near the top of the range for their role, and compensation decisions are dependent on the facts and circumstances of each role and individual. 

Commitment to Equal Pay

At HealthJoy, we are committed to creating a diverse and inclusive workplace where everyone has the opportunity to succeed and thrive.

We believe that everyone should be paid based on their qualifications, experience, and the work that they do, and not on their gender, race, or any other personal characteristic. Our compensation practices are essential to fostering a diverse and inclusive culture where we value the contributions of all our employees. 

We conduct thorough annual reviews of employee pay and our pay practices to ensure we reward the right behaviors and are providing equal pay for equal work. 

Additionally, we assess the external market and internal equity across like roles. As part of our regular review of pay practices, HealthJoy examines employee pay for potential disparities between persons of different genders, races and ethnicities that are not explainable by objective factors such as performance, experience level, credentials, or location, and are committed to correcting any issues and reviewing practices from unintended outcomes. 

Commitment to Equal Opportunity

HealthJoy is committed to creating a diverse environment and is proud to be an equal opportunity employer. 

All qualified applicants receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or any other basis forbidden under federal, state, or local law.

Don’t meet every single requirement? We know the confidence gap and imposter syndrome can get in the way of meeting spectacular candidates, so please don’t hesitate to apply — we’d love to hear from you. HealthJoy is dedicated to building a diverse, inclusive, and authentic workplace, so if you’re excited about this role and HealthJoy, we encourage you to apply. You may be just the right candidate for this or other roles.