Broker Sales Manager

We’re hiring a Broker Sales Manager to play a pivotal role in expanding our broker relationships and helping employer groups gain more control over healthcare spend and plan design. This is a fast-moving, roll-up-your-sleeves environment—ideal for someone with experience in benefits/stop-loss who wants more ownership, bigger impact, and a path toward leadership.

This role is primarily inside sales (very limited travel; occasional events if desired).

What You’ll Do 

• Build and grow broker partnerships by confidently engaging brokers and executive stakeholders, creating trust, and developing a durable referral network.
• Own the sales process end-to-end—prospecting, discovery, proposal development, presentations, follow-up, and closing—while consistently delivering against monthly and annual targets.
• Create compelling, broker-ready deliverables (proposals, presentations, census/data inputs, and RFP responses) that clearly tell the True Captive story and recommended solution.
• Drive smooth implementations by coordinating across internal teams and external partners, gathering required paperwork, anticipating issues, and resolving broker/client questions quickly and thoughtfully.

What You Bring 

• Experience in employee benefits with a strong working knowledge of self-funded health plans; exposure to medical stop-loss and/or captives strongly preferred.
• Proven ability to sell consultatively (especially through brokers), with strong business acumen, follow-through, and comfort engaging executives.
• Strong proposal/presentation writing skills—able to turn complex concepts into a simple, compelling story with high attention to detail.
• Organized, self-directed, and collaborative—comfortable juggling priorities in a fast-paced, evolving environment (CRM experience such as HubSpot is a plus).

Helpful Skills / Tools

• Microsoft Office proficiency (Excel/PowerPoint/Word)
• CRM comfort (HubSpot preferred; Salesforce exposure welcome)
• Strong written, verbal, and presentation communication skills

Why This Role

• You’ll sell a solution with real impact—helping employers take control of healthcare costs while making benefits easier to understand.
• You’ll join a team of “relentless problem solvers” who value initiative, clarity, and collaboration.
• You’ll have room to grow—this is a strong stepping stone into broader leadership as the organization scales.