Sales Development Manager, Sidecar Health
Plus bonus opportunity, and equity package
Digital health insurance platform
Be an early applicant
Digital health insurance platform
201-500 employees
Be an early applicant
Plus bonus opportunity, and equity package
201-500 employees
Company mission
To make healthcare affordable.
Role
Who you are
- 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 the job involves
- 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
- 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
Our take
Sidecar Health’s insurtech platform allows users to tailor their own flexible healthcare plans based on their individual needs and budget. One of its main advantages outside of its flexibility is how the company doesn't use its own dedicated network of doctors, allowing the customer to see whomever they like while negating its own need to build nationwide networks.
On top of this it allows users to search and compare local health providers, and pay directly for care through its own payment card, often at a discount to what legacy insurance providers charge. Sidecar’s offering allows for better flexibility, more transparency and fewer financial burdens for unnecessary coverage areas.
The company has garnered plenty of praise, and financial backing, for its consumer-centric approach - and its latest raise positions Sidecar Health as a major disruptor in the market. That said, future growth will depend on how well it can expand its nationwide footprint, take on the legacy healthcare providers and work its way into employer and government-sponsored plans.
Steph
Company Specialist at Welcome to the Jungle
Insights
-28% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Jun 2024
$165m
SERIES D
Jan 2021
$125m
SERIES C
Total funding: $328m
Company benefits
- Comprehensive Medical, Dental, and Vision benefits
- Paid vacation and company holidays
- Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S
Company HQ
El Segundo, CA
Leadership
Patrick Quigley
(Co-Founder & CEO)Having worked at BEA Systems and QuinnStreet for a combined 8 years, they took an MBA at Wharton. They also served as CEO of Healthplans.com and Katch.
Veronica Osetinsky
(Co-Founder & COO)They studied at UCB before working at Bank of America and Paramax Capital. They worked at Quinstreet and Katch for 8 years prior to co-founding Sidecar Health.
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