Clover Health: Chief Actuary Remote

The Finance team at Clover Health is a group of strategic partners providing financial and operational insights that drive informed decision-making and efficient capital allocation. Guided by our core values of excellence, accountability, and collaboration, we provide actionable recommendations to improve health outcomes and reduce costs while ensuring financial integrity and innovation.

Actuarial is at the center of some of Clover’s most important decisions—from pricing and forecasting to reserving, medical economics, and long-term strategy. As Chief Actuary, you’ll lead and evolve this function during a pivotal stage of the company’s growth, helping shape how we deploy AI, automation, and advanced analytics to improve decision-making across the business.

This isn’t a traditional Chief Actuary role. We’re looking for someone who can combine deep actuarial expertise with modern technology, building AI-enabled workflows that transform how actuarial work gets done while maintaining the rigor, transparency, and governance required in a highly regulated environment. You’ll partner closely with leaders across Finance, Clinical, Growth, Operations, and Product to influence company strategy while building a best-in-class actuarial organization.

As a Chief Actuary, you will:

• Lead Clover’s enterprise actuarial function, including pricing, forecasting, reserving, medical economics, Part D, Stars analytics, and bid strategy.
• Establish the long-term vision for actuarial, modernizing the function through AI, automation, and scalable analytical infrastructure. 
•  Build AI-enabled workflows that reduce manual effort, accelerate insight generation, and improve actuarial decision-making while ensuring explainability, governance, and regulatory compliance.
• Lead the annual Medicare Advantage bid strategy and pricing process, framing tradeoffs among growth, competitiveness, margin, risk, and capital requirements to support enterprise planning and executive decision-making.
• Assume responsibility for actuarial opinions, reserve adequacy, and related regulatory actuarial requirements, including transitioning responsibilities currently supported by external actuarial partners.
• Guide reserving methodology, IBNR development, forecasting, and emerging experience analysis to provide timely, reliable financial insights.
• Partner with Finance leadership to strengthen forecasting, planning, capital management, and enterprise performance measurement.
• Collaborate with Medical Economics to identify healthcare cost trends, evaluate interventions, and develop strategies that improve member outcomes while managing medical expense. 
•  Drive adoption of modern analytics tools and AI capabilities across the actuarial organization, helping the team operate faster, smarter, and with greater transparency.
• Serve as a trusted advisor to executive leadership, translating complex actuarial concepts into clear business recommendations. 
• Lead, develop, and scale a high-performing actuarial organization, including organizational design, performance management, workforce capacity, and development of actuarial and analytical talent.
• Build strong partnerships across Finance, Clinical, Operations, Growth, Data Science, and Engineering to ensure actuarial insights are embedded in strategic decision-making.
• Establish and maintain actuarial governance, model review, documentation, control, and validation standards that support regulatory compliance, financial integrity, and sound executive decision-making.

Success in this role looks like:

First 90 Days

• Build trusted relationships across Finance and key business partners. 
•  Assess the current actuarial organization, tools, and operating model.
• Develop a roadmap for AI adoption and workflow automation across the actuarial function.
• Gain deep familiarity with Clover’s pricing, forecasting, reserving, and medical economics processes.

First 6 Months

• Begin implementing AI-enabled actuarial workflows that improve efficiency and insight generation.
• Strengthen forecasting, reserving, and bid processes through improved automation and cross-functional collaboration.
• Successfully assume ownership of additional actuarial responsibilities, including reserve oversight and governance.
• Establish a clear long-term organizational vision for the actuarial function.

Long Term

• Build one of the industry’s most modern actuarial organizations by combining deep actuarial science with AI-enabled decision support.
• Improve forecasting accuracy, operational efficiency, and enterprise decision-making through advanced analytics and automation.
• Develop a highly engaged, high-performing actuarial team that is recognized as a strategic partner across the organization.

You should get in touch if:

• You are a Fellow of the Society of Actuaries (FSA) and a Member of the American Academy of Actuaries.
• You have significant leadership experience in Medicare Advantage actuarial functions, including pricing, reserving, forecasting, and bid development.
• You are an AI evangelist and have demonstrated experience deploying AI workflows across your functional areas. Moreover, you are enthusiastic about applying automation and modern tooling to fundamentally improve the actuarial function.
• You have experience leading large, cross-functional initiatives that influence executive decision-making.
• You are equally comfortable discussing actuarial methodology with technical experts and communicating business implications to executives and non-technical stakeholders. 
• You have a track record of building, mentoring, and developing high-performing actuarial teams.
• You thrive in fast-moving environments where you can build, innovate, and shape the future of an organization.

Benefits Overview:  

• Financial Well-Being: Our commitment to attracting and retaining top talent begins with a competitive base salary and equity opportunities. Additionally, we offer a performance-based bonus program, 401k matching, and regular compensation reviews to recognize and reward exceptional contributions.
• Physical Well-Being: We prioritize the health and well-being of our employees and their families by providing comprehensive medical, dental, and vision coverage. Your health matters to us, and we invest in ensuring you have access to quality healthcare.
• Mental Well-Being: We understand the importance of mental health in fostering productivity and maintaining work-life balance. To support this, we offer initiatives such as No-Meeting Fridays, monthly company holidays, access to mental health resources, and a generous flexible time-off policy. Additionally, we embrace a remote-first culture that supports collaboration and flexibility, allowing our team members to thrive from any location. 
• Professional Development: Developing internal talent is a priority for Clover. We offer learning programs, mentorship, professional development funding, and regular performance feedback and reviews.

Additional Perks:

• Employee Stock Purchase Plan (ESPP) offering discounted equity opportunities
• Reimbursement for office setup expenses
• Monthly cell phone & internet stipend
• Remote-first culture, enabling collaboration with global teams
• Paid parental leave for all new parents
• And much more!

About Clover: We are reinventing health insurance by combining the power of data with human empathy to keep our members healthier. We believe the healthcare system is broken, so we’ve created custom software and analytics to empower our clinical staff to intervene and provide personalized care to the people who need it most.

We always put our members first, and our success as a team is measured by the quality of life of the people we serve. Those who work at Clover are passionate and mission-driven individuals with diverse areas of expertise, working together to solve the most complicated problem in the world: healthcare.

From Clover’s inception, Diversity & Inclusion have always been key to our success. We are an Equal Opportunity Employer and our employees are people with different strengths, experiences, perspectives, opinions, and backgrounds, who share a passion for improving people’s lives. Diversity not only includes race and gender identity, but also age, disability status, veteran status, sexual orientation, religion and many other parts of one’s identity. All of our employee’s points of view are key to our success, and inclusion is everyone’s responsibility.

#LI-REMOTE

Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records. We are an E-Verify company.