Sales Development Representative, Remote

Sidecar Health is redefining health insurance with a mission to make excellent healthcare affordable and attainable for everyone. They are seeking a Sales Development Representative (SDR) to create first impressions and open doors for the sales team in a fast-paced, high-ownership environment.

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

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