Director of Underwriting

Remote

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Not SpecifiedCompensation

Expert & Leadership (9+ years)Experience Level

Full TimeJob Type

UnknownVisa

Health Insurance, HealthcareIndustries

Requirements

Candidates must possess a Bachelor's degree and at least 8 years of progressive experience in group underwriting within health insurance or healthcare-related financial services, including leadership and decision-making responsibilities. Proven ability as a player-coach, success partnering with Sales, deep knowledge of group underwriting methodologies, funding arrangements, stop-loss, and healthcare cost drivers are essential. Strong analytical, problem-solving, communication, negotiation, and relationship-building skills are required, along with comfort in a fast-paced, high-growth environment. Familiarity with reinsurance markets and strategies is preferred.

Responsibilities

The Director of Underwriting will lead the group underwriting function, personally underwriting complex cases, and managing the day-to-day operations of the underwriting team. This role involves leading, mentoring, and developing underwriters, establishing underwriting guidelines and policies, and partnering with Sales to support new business growth and client relationships. Responsibilities include providing creative underwriting solutions, collaborating with cross-functional teams on pricing and renewals, approving escalated underwriting decisions, monitoring performance, and building relationships with brokers, consultants, and reinsurers. The Director will also promote a culture of accountability and continuous improvement within the underwriting function.

Skills

Group Underwriting

Underwriting Guidelines

Risk Management

Financial Performance

Sales Support

Team Leadership

Mentoring

Process Improvement

Healthcare

Insurance

Sidecar Health

Affordable health insurance with price transparency

About Sidecar Health

Sidecar Health provides health insurance plans that focus on affordability and transparency, including options compliant with the Affordable Care Act (ACA). The company allows members to see average cash prices for medical services upfront, helping them make informed decisions and avoid unexpected costs. Revenue is generated through member premiums, which cover medical expenses, while also benefiting from the difference between negotiated cash prices and premiums. Sidecar Health's goal is to empower members to take control of their healthcare expenses with straightforward and cost-effective insurance options.

El Segundo, CaliforniaHeadquarters

2018Year Founded

$319.1MTotal Funding

SERIES_DCompany Stage

Financial Services, HealthcareIndustries

201-500Employees

Benefits

Health Insurance

Dental Insurance

Vision Insurance

401(k) Retirement Plan

Paid Vacation

Paid Holidays

Stock Options

Company Equity

Risks

Increased competition from similar insurtech companies may erode market share.

Regulatory scrutiny on cash pay models could pose compliance challenges.

Economic downturns might reduce consumer spending on health insurance premiums.

Differentiation

Sidecar Health offers transparent pricing, empowering members with upfront healthcare cost information.

The company provides customizable plans, aligning with individual coverage needs and budgets.

Partnerships with institutions like Ohio State University enhance their fixed-price care model.

Upsides

Recent $165M Series D funding supports expansion and innovation in health insurance.

Partnership with Mark Cuban Cost Plus Drug Company lowers prescription drug costs for members.

ACA-compliant product line expansion increases market reach and consumer options.

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