Director of Underwriting job opportunity at Sidecar Health.

Home Jobs In Same As Address Tag: Actuary Director of Underwriting position at Sidecar Health


bot
Sidecar Health Director of Underwriting
Experience: 8-years
Pattern: Remote
Walk In
apply Apply Now
Salary:
Status:

Actuary

Copy Link Report
degreeOND
Hiring inbound within Remote

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen. The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent. If you want to use your talents to transform healthcare in the United States, come join us!About the Role The Director of Underwriting will lead Sidecar Health’s group underwriting function while also serving as a hands-on contributor. Reporting to the VP of Actuarial & Underwriting, this role is both a player-coach and a growth partner — directly underwriting complex, high-value cases while managing, mentoring, and developing a team of underwriters. They will partner closely with Sales and Client Success to support new business opportunities, renewals, and finalist presentations, playing a critical role in driving profitable growth and strengthening Sidecar Health’s presence in the market.  What You'll Do Serve as both a leader and contributor, personally underwriting large and complex group cases while managing the day-to-day operations of the underwriting team  Lead, mentor, and develop a team of group underwriters, fostering consistency, accuracy, and professional growth  Establish and maintain underwriting guidelines, policies, and processes that balance competitiveness, risk, and profitability  Partner with Sales to support new business growth, participating in finalist meetings and broker/consultant discussions as needed  Provide creative underwriting solutions that help win new accounts while protecting financial performance  Collaborate cross-functionally with Actuarial, Product, Finance, and Client Success to inform pricing strategies, renewals, and long-term client value  Review and approve escalated underwriting decisions, applying expert judgment to ensure alignment with strategy  Monitor underwriting performance and portfolio results, identifying trends and implementing corrective actions when necessary  Build and maintain strong relationships with brokers, consultants, and reinsurers to enhance growth opportunities and support reinsurance strategies  Promote a culture of accountability, collaboration, and continuous improvement within the underwriting function  What You'll Bring 8+ years of experience in group underwriting within health insurance or healthcare-related financial services, with progressive responsibility in leadership and decision-making  Proven ability as a “player-coach” — comfortable leading a team while directly underwriting complex, high-profile cases  Demonstrated success partnering with Sales to win new business and support strategic client relationships  Deep knowledge of group underwriting methodologies, funding arrangements (fully insured, self-funded/ASO), stop-loss, and healthcare cost drivers  Strong analytical and problem-solving skills with the ability to balance growth opportunities against risk considerations  Executive presence with excellent communication, negotiation, and relationship-building skills  Familiarity with reinsurance markets and strategies preferred  Comfort operating in a fast-paced, high-growth environment where adaptability is key  Bachelor’s degree  What You'll Get Competitive salary, bonus opportunity, and equity package   Comprehensive Medical, Dental, and Vision benefits A 401k retirement plan Paid vacation and company holidays Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S. Sidecar Health is an Equal Opportunity employer committed to building a diverse team. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status.

Other Ai Matches

remote-jobserver Remote
Lead Product Manager Applicants are expected to have a solid experience in handling Product and Design related tasks
remote-jobserver Remote
Senior Manager, Business Process Excellence Applicants are expected to have a solid experience in handling Member Care and Claims related tasks
remote-jobserver Remote
Senior Product Manager Applicants are expected to have a solid experience in handling Product and Design related tasks
remote-jobserver Remote
Director of Underwriting Applicants are expected to have a solid experience in handling Actuary related tasks
remote-jobserver Remote
Sales Development Representative Applicants are expected to have a solid experience in handling Marketing related tasks
remote-jobserver Remote
Sales Development Representative, Remote Applicants are expected to have a solid experience in handling Marketing related tasks
remote-jobserver Remote
Sales Development Representative, Remote Applicants are expected to have a solid experience in handling Marketing related tasks
remote-jobserver Remote
Regional Sales Manager, Georgia (Remote) Applicants are expected to have a solid experience in handling Sales related tasks
remote-jobserver Remote
Director of Product Management Applicants are expected to have a solid experience in handling Product and Design related tasks
remote-jobserver Remote
Regional Sales Manager, Group Health Plans (Georgia) Applicants are expected to have a solid experience in handling Sales related tasks
remote-jobserver Remote
Customer Service Representative, Member Care Applicants are expected to have a solid experience in handling Member Care and Claims related tasks
remote-jobserver Remote
Sales Development Representative, Remote Applicants are expected to have a solid experience in handling Marketing related tasks