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 Sales Development Manager at Sidecar Health is a true player-coach: you’ll lead, develop, and motivate a team of SDRs while also staying actively involved in outbound strategy, messaging, and top-of-funnel execution yourself. This role blends leadership with hands-on contribution — perfect for someone who loves coaching but still enjoys getting in the trenches to prospect, refine sequences, test messaging, and model excellence. You’ll drive pipeline generation, increase conversion quality, and build a high-performance culture grounded in accountability, clarity, and continuous improvement.
What You’ll Do
- Serve as a player-coach: lead a team and personally contribute to outbound strategy, messaging refinement, and high-priority prospecting efforts
- Coach, train, and elevate SDRs through call reviews, live role-plays, skill sessions, and feedback loops
- Run structured weekly operating rhythms across the team (huddles, coaching, pipeline reviews)
- Partner with Sales, Marketing, and RevOps to align ICP, personas, value props, and outbound campaigns
- Analyze SDR performance metrics (activity levels, conversion rates, meeting quality, pipeline contribution) and use insights to drive improvement
- Maintain operational excellence in Salesforce, Outreach, and LinkedIn Navigator
- Hire, onboard, and ramp new SDRs to full productivity
- Model Sidecar Health’s standards of clarity, credibility, and member-first communication in your own outbound work
- Build repeatable systems that drive week-over-week improvement across the team
What You'll Bring
- 2+ years of experience managing SDRs or BDRs in a high-volume outbound environment
- A proven ability to succeed as a player-coach — someone comfortable leading AND contributing hands-on
- Strong coaching ability: you love developing reps and elevating skillsets through call coaching and messaging refinement
- Deep knowledge of outbound prospecting, sequencing, objection handling, and discovery fundamentals
- Data-driven decision-making with the ability to diagnose bottlenecks and drive conversion improvement
- Operational rigor; you bring structure and consistency to a fast-paced environment
- Experience with Salesforce, Outreach, and LinkedIn Navigator (or willingness to learn quickly)
- Growth mindset — resourceful, coachable, and committed to improving just like your team
- Excellent communication skills, presence, and a bias toward action
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.
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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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