Regional Vice President of Sales, ASO

Remote

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Not SpecifiedCompensation

Expert & Leadership (9+ years)Experience Level

Full TimeJob Type

UnknownVisa

Health Insurance, HealthcareIndustries

Requirements

Candidates must have a Bachelor's degree and at least 8 years of experience selling health insurance, healthcare services, or related solutions to national or jumbo accounts (10k+ lives). Proven success in enterprise sales, consistently meeting or exceeding new business sales targets within ASO and self-funded employer groups, is required. Strong broker and consultant relationships, a deep understanding of ASO models, healthcare cost containment strategies, and employer benefits dynamics are essential. The ideal candidate will possess executive presence with excellent presentation, negotiation, and closing skills, and the ability to thrive in a fast-paced, high-growth environment with an entrepreneurial mindset and comfort operating with ambiguity.

Responsibilities

The Regional Vice President of Sales, ASO, will own the full sales cycle for ASO/NASA prospects, from pipeline generation through contract execution. This role involves cultivating and expanding strategic relationships with national benefits consultants, brokers, and employer decision-makers, and driving consultative sales conversations to articulate Sidecar Health’s value proposition and ROI. Responsibilities include partnering with internal teams to develop tailored solutions, delivering executive-level pitches, negotiating deal structures and contracts, and consistently meeting or exceeding new business sales goals and revenue targets. The role also requires maintaining accurate pipeline management and reporting, representing Sidecar Health at industry events, and partnering with leadership to shape go-to-market strategies and refine sales playbooks for the ASO segment.

Skills

ASO sales

Sales cycle management

Pipeline generation

Contract negotiation

Relationship management

Consultative selling

Value proposition articulation

ROI analysis

Health insurance

Self-funded employer groups

Benefits consultants

Brokers

National accounts

Jumbo accounts

Executive-level presentations

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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