[Remote] Sales Development Representative at Sidecar Health

Remote

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Not SpecifiedCompensation

Entry Level & New Grad, Junior (1 to 2 years)Experience Level

Full TimeJob Type

UnknownVisa

Healthcare, Health Insurance, SaaSIndustries

Requirements

1+ year of experience in an outbound SDR/BDR role or similar high-volume prospecting environment
Strong communication skills and comfort reaching out to prospects through multiple channels
Ability to manage structured daily activity while staying organized and resilient
Familiarity with Salesforce, Outreach, and LinkedIn Navigator (or willingness to learn quickly)
A growth mindset — coachable, driven, and committed to improving each week
Track record (or clear potential) for hitting meeting goals, converting qualified leads, and contributing to pipeline
Professional presence, attention to detail, and a genuine desire to build a career in sales

Responsibilities

Prospect into target accounts through outbound calls, emails, LinkedIn outreach, and multi-touch sequences
Hit daily and weekly activity expectations with consistency and urgency
Conduct light discovery to qualify interest, fit, and buying readiness
Book high-quality meetings that convert into real opportunities for our sales team
Maintain clean data in Salesforce and follow the SDR playbook for messaging and sequencing
Collaborate with Regional Sales Managers and the SDR Manager to refine outreach, improve conversion rates, and share learnings
Bring energy and ownership — participate in call coaching, team huddles, and skill-building sessions
Represent Sidecar Health with credibility, clarity, and a member-first mindset
Deliver results: consistent meeting attainment, strong conversion quality, clean operational execution, and week-over-week improvement

Skills

Outbound Prospecting

Cold Calling

Email Outreach

LinkedIn Outreach

Salesforce

Lead Qualification

Discovery Calls

Multi-Touch Sequences

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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