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
As an Sales Development Representative at Sidecar Health, you are the first reason an employer believes we're different - showing up with curiosity, energy, and a product that's genuinely worth getting excited about! We're reimagining how employers and their members experience healthcare, and that's a story worth telling.
This role is for someone who is passionate about the mission, thrives in a performance-driven environment, and wants to grow alongside a product that's changing lives.
What You’ll Do
- 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
What You'll Bring
- 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
What You'll Get
- Competitive base salary ($60,000) with uncapped performance-based commission and equity
- 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.
Sidecar Health Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Sidecar Health and has not been reviewed or approved by Sidecar Health.
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Fair & Transparent Compensation — Compensation in tech and product roles is described as market‑aligned and competitive. Feedback suggests many in these functions feel total pay stacks up well against peers.
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Healthcare Strength — Employer‑paid major‑medical coverage for employees and family is highlighted, positioning health benefits as a strong component of total rewards. Feedback suggests low denial rates, added navigation tools, and center‑of‑excellence partnerships reinforce the plan’s practical value.
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Equity Value & Accessibility — Total rewards are presented to include stock options and bonuses in addition to salary. Feedback suggests these elements can meaningfully enhance perceived upside beyond base pay.
Sidecar Health Insights
What We Do
Sidecar Health is changing the health industry with modern, common-sense health insurance that finally gives consumers control over costs and choices. We are a passionate group of people-people on a mission to make quality healthcare affordable and accessible for everyone.
Why Work With Us
Being a growth-stage distributed startup, transparent and asynchronous communication is critical. We'll provide you with the resources and tools you need, and regularly seek your feedback through quarterly engagement pulses on what is or isn't working well.
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