Company Overview

Our client is a venture-backed startup revolutionizing how small and mid-sized businesses manage group health insurance. By pooling employers into group captives, the company provides a powerful, cost-effective alternative to traditional PEOs and fully insured plans. With underwriting support from a major national carrier and access to a strategic partner’s customer base, this business is primed for growth. Backed by experienced operators and financial support, the company is poised to reshape the employer healthcare benefits market and is now building its foundational leadership team.

Position Overview

Our client is seeking a Vice President of Sales to take full ownership of the company’s go-to-market execution. This is the first senior commercial hire outside of the founding team and presents a rare opportunity to shape sales strategy from the ground up. The VP will be responsible for converting early interest into revenue, building scalable sales processes, and ultimately growing a high-performing sales organization in a high-potential, underserved segment.

Position Responsibilities

• Lead all aspects of the sales function, from strategy to execution.
• Define and implement scalable sales processes including CRM cadences and pipeline management.
• Educate employers and HR leaders on alternatives to traditional health plans and PEOs.
• Drive net-new business through direct sales, broker networks, and channel partnerships.
• Convert warm leads and early traction into revenue-generating clients.
• Serve as a player-coach: actively closing deals while mentoring future sales hires.
• Collaborate with the SDR/lead qualification team and VP of Operations to align efforts.
• Represent the company through association events and industry education initiatives.
• Report to the CEO and work closely with executive leadership on forecasting, operations, and strategic planning.

Position Qualifications

• 10+ years of B2B sales experience in insurance, healthcare benefits, or employer-facing services.
• Proven success building and leading sales teams in startup or high-growth environments.
• Strong understanding of SMB and mid-market employer segments.
• Process-driven with expertise in sales operations (forecasting, KPIs, CRM best practices).
• Track record of success in relationship-driven sales cycles.
• Hands-on, entrepreneurial approach with a bias for action.
• Strong strategic thinking with willingness to execute in the field.

Preferred:

• Experience selling group captives, self-funded insurance models, or benefit consulting services.

What They Offer

• Opportunity to build a sales engine from the ground up in a high-growth industry.
• Strategic equity potential and performance-driven incentives.
• Collaborative, entrepreneurial environment with direct access to the CEO and founding team.
• Mission-driven culture focused on improving health coverage for growing businesses.
• Backed by strong underwriting partners and customer access through strategic relationships.

Talentfoot Overview

Talentfoot Executive Search specializes in future-proofing organizations by securing forward-thinking leaders across sales, marketing, eCommerce, product, data, operations, finance, and technology with a track record of accelerating growth, innovation, and profitability. Since 2010, we’ve partnered with more than 2,500 companies and lead the industry with a 98% customer success rate. Learn more at Talentfoot.com.

Apply Today

If you are a sales leader excited by the opportunity to drive growth in a disruptive health benefits model, apply today and help shape the future of group insurance for SMBs.