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Head Actuary

All of us can agree healthcare is simply too hard in the US. And our members feel that pain day in and day out. We aim to create an experience that simply feels easy when you need to access our healthcare system. If you need something, you know where to go to get it with care that is a click (or as few clicks as possible!) away.


What’s beautiful about a vision oriented toward “easy” is how it imparts a singular feeling. We instinctively know as humans when something is easy versus hard, even if we can’t explain why. We fight as a company to make an easy pathway available to all our members at every stage of their healthcare journey. If you feel passionate about delivering better healthcare to small businesses through a seamless care experience and affordable benefits, join us!


We are seeking a Head Actuary to manage Sana’s core actuarial and underwriting functions, including pricing, reserving, quoting, reinsurance, plan design, regulatory strategy, and consulting on strategic initiatives. The ideal candidate possesses significant experience in the level-funded industry and demonstrated experience leading high-performing actuarial teams. At the same time, that person brings a collaborative and flexible entrepreneurial mindset that is critical in a startup environment. Reporting to the President/Chief Operating Officer, this role serves as a key member of Sana’s leadership team and works closely with leaders in Revenue, Finance, Product/Engineering, Legal, Care Team, and Operations.


We are building a distributed operations team and encourage all applicants to apply, regardless of location. 


What you will do:
  • Own the strategic vision and delivery of excellent work for the actuarial and underwriting team. You will lead a critical aspect of Sana’s business and work cross-functionally to craft a plan to achieve our strategic priorities. 
  • Lead and continue to build a high-performing team consisting of actuaries and underwriters. Develop and foster plans for continued career growth through regular coaching, consistent 1:1s, feedback sessions, problem solving, and Q&A during normal business hours. 
  • Manage the long-term performance of Sana’s loss ratios while owning the day-to-day functions related to our proprietary rate manual, predictive analytics partners, pricing, and reserving; at the same time, strategically balance areas of profitability to deliver competitive rates, maximize Sana’s profitability, and manage cash flow.
  • Build enduring relationships with our reinsurance treaty partners and own the day-to-day relationships with our stop loss broker, fronting carriers, rating manual, and risk/data providers to ensure Sana has sufficient reinsurance capacity at desirable terms.
  • Support the smooth running of new business and renewal quoting while managing ad hoc trade-offs on difficult underwriting, pricing or reserving issues with the right blend of judgment and data-informed decision-making, including any escalations during normal business hours.
  • Contribute meaningfully to the development of our insurance products: policy contracts, rate plans, actuarial factors, and rating methods, state filings, expense ratio analysis, and underwriting rules.
  • Work cross-functionally with a variety of stakeholders to support strategic initiatives related to financial forecasting, data analytics, regulatory strategy, provider contracting, care delivery, partnership, and product development.
  • Develop a deep understanding of Sana’s claims and medical data in order to deliver insightful, detailed analyses on all things related to medical economics at Sana.
  • Responsible for monthly as well as ad hoc reporting on our underwriting performance, loss ratio results, and other relevant findings to core stakeholders, from external parties such as reinsurance partners and fronting carriers to internal stakeholders across all departments.
  • Issue actuarial opinions regarding Sana’s written insurance contracts, including loss ratio projections and sufficiency of reserves and capital, as needed.
  • Drive innovation in Sana’s predictive modeling and data analysis methods in collaboration with our Product, Data, and Engineering teams.
  • Generally improve our approach to underwriting based on performance and price competitiveness to take calculated risks and drive best-in-class small group underwriting.


About you:
  • 10+ years of relevant work experience, of which a meaningful portion must be in the level-funded and/or medical stop loss industry, and credentialed actuary (ASA or FSA, MAAA). Bonus points for prior experience in high-growth startups and/or the Insurtech space.
  • Exceptional analytical skills with a demonstrated ability to look at data regularly to find trends, drill down into cases as needed, and take data-informed action accordingly. Experience with SQL, Excel, and business intelligence tools such as Mode/Tableau is required.
  • Proficient in the financial reporting requirements of insurance companies, including statutory, GAAP, and tax reporting.
  • Excellent people manager and strong team player with a track record of working cross-functionally. People love working with and for you.
  • Outstanding communication skills in-person, over the phone, in writing, via email, chat, carrier pigeon, etc.
  • Unparalleled attention to detail. You love getting into the weeds to get things done.
  • Gritty. You’re willing to jump into any of the team’s work and support. We’re a small team and sometimes when a few of us are out, we all need to help fill in for each other.
  • You are mission-driven. You care about making our healthcare system work better for people and business owners.
  • You ask questions from a place of genuine curiosity and humility.
  • You assume positive intent and meet your teammates with compassionate candor to solve problems together.
  • You remain flexible, resilient, and foster a culture of continuous learning even in the face of hardship. 
  • You bring a bias for action paired with intelligent risk-taking.
  • You follow through on your commitments and foster trust with your colleagues. 


Benefits:
  • Stock options in rapidly scaling startup
  • Flexible vacation
  • Medical, dental, and vision Insurance 
  • 401(k) and HSA plans
  • Parental leave
  • Remote worker stipend
  • Opportunity for career growth
  • Dynamic start-up environment


$225,000 - $295,000 a year
Our cash compensation amount for this role is targeted at $225,000 - $295,000 per year for all US-based remote locations. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.
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CEO of Sana Benefits
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Will Young
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Average salary estimate

$260000 / YEARLY (est.)
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$225000K
$295000K

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Full-time, remote
DATE POSTED
July 19, 2025
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