Regional Sales Manager, Broker Sales (Dallas)

What You’ll Do

• Own and scale Sidecar Health’s broker growth strategy in your region - equipping brokers and GAs with the knowledge, tools, and confidence to win
• Build deep, trusted relationships with brokers, GAs, and distribution partners, becoming a go-to expert in your market
• Identify high-potential distribution partners to invest in and grow with over time
• Serve as the face of Sidecar Health locally, representing us at broker events, industry meetings, and community gatherings
• Identify, test and refine new go-to-market and growth strategies, sharing insights to shape national sales efforts
• Consistently meet or exceed sales goals while delivering an exceptional partner experience
• Bring competitive intelligence and market insights to inform product and strategy decisions

What You’ll Bring

• 4+ years of sales experience within healthcare, benefits, or adjacent industries such as PBM, ancillary benefits, stop-loss, PEO, payroll, dental, vision, or B2B software
• Experience calling on brokers and/or agencies preferred, but not required
• Bachelor’s degree
• Proven ability to generate and develop new opportunities, including self-sourced leads, without relying on pre-existing broker networks
• Strong relationship-building and influencing skills in a consultative, trust-based sales environment
• Track record of meeting or exceeding growth or revenue goals
• Experience using market data and competitive insights to prioritize efforts and improve performance
• Comfort with targeted outreach, networking, and in-market presence—prioritizing long-term partnerships over high-volume call activity
• Willingness to travel up to 40% within Texas to build and deepen regional relationships

What You'll Get

• Competitive base salary with uncapped performance-based commission and equity
• Comprehensive Medical, Dental, and Vision benefits
• 401(k) retirement plan
• Paid time off and company holidays
• A seat at the table in shaping how Sidecar Health goes to market as we scale

About the Role

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.

Benefits

• Comprehensive Medical, Dental, and Vision benefits
• 401(k) retirement plan
• Paid time off and company holidays

Pay

• Competitive base salary with uncapped performance-based commission and equity

Schedule

• Flexible work schedule

Qualifications

• 4+ years of sales experience within healthcare, benefits, or adjacent industries such as PBM, ancillary benefits, stop-loss, PEO, payroll, dental, vision, or B2B software
• Experience calling on brokers and/or agencies preferred, but not required
• Bachelor’s degree
• Proven ability to generate and develop new opportunities, including self-sourced leads, without relying on pre-existing broker networks
• Strong relationship-building and influencing skills in a consultative, trust-based sales environment
• Track record of meeting or exceeding growth or revenue goals
• Experience using market data and competitive insights to prioritize efforts and improve performance
• Comfort with targeted outreach, networking, and in-market presence—prioritizing long-term partnerships over high-volume call activity
• Willingness to travel up to 40% within Texas to build and deepen regional relationships

Skills

• Excellent communication and interpersonal skills
• Ability to build and maintain strong relationships with clients and partners
• Strong analytical and problem-solving skills
• Ability to manage multiple projects and priorities simultaneously
• Proficiency in Microsoft Office Suite

Sidecar Health is an Equal Opportunity Employer

We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status.