Sales Development Representative - Remote

Overview

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.

In Short

• 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

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

Benefits

• 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.