Client Success Specialist

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and attainable 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!

**Must reside in Florida for consideration**

About the Role

We’re looking for a Client Success Specialist who’s passionate about delivering exceptional service and creating seamless experiences for our clients and brokers. In this role, you’ll lead enrollment meetings, support Spanish-speaking members, and partner with our Account Management team on key initiatives — all while helping shape how people understand and engage with Sidecar Health.

This is a great opportunity to jumpstart a career in Client Success or Account Management with a mission-driven company and a dynamic, supportive team.

What You’ll Do

• Lead and facilitate open enrollment and employee engagement meetings (on-site, virtual, and recorded)
• Serve as a bilingual resource to support members and brokers in FL, GA, and OH markets
• Translate and deliver key benefits communications, marketing materials, and presentations in Spanish
• Support Account Managers with post-sale implementations, ongoing account servicing, and engagement campaigns
• Maintain accurate documentation of client interactions, meeting notes, and follow-ups in CRM systems
• Coordinate logistics and materials for client and broker meetings, including scheduling and prep
• Partner with Sales and Marketing to tailor messaging and materials for specific client groups
• Stay up to date on product offerings, compliance updates, and market trends to provide accurate information
• Identify and escalate member or client issues as needed to internal teams (e.g., Member Care, Product, Compliance)

What You'll Bring

• Bilingual in Spanish (required)
• Florida 2-15 license (required)
• Must reside in the state of Florida
• Willingness to travel 50–75% (including some overnight travel across Florida and Georgia)
• 1–2+ years of experience in client success, account coordination, health insurance, or employee benefits (preferred)
• Experience leading benefit or open enrollment meetings (highly preferred)
• Excellent communication, presentation, and interpersonal skills — confident speaking to groups and individuals
• Strong organizational skills and attention to detail; able to juggle multiple tasks and deadlines
• Familiarity with CRM tools, G-Suite, and Slack (bonus points for experience with Salesforce or similar platforms)
• Bachelor’s degree or equivalent from an accredited university

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.