Sales Director - Middle Market, Southwest Region

About Tokaido Health Tokaido Health is an AI-native medication navigation platform that helps self-insured employers dramatically reduce the cost of specialty medications and infusions – without disrupting plan design or changing PBMs. We combine infusion site-of-care navigation, biosimilar substitution, and formulary optimization into a single platform, backed by behavioral economics-driven incentives that actually move members to act.

We closed our seed round in April 2026 with backing from Norwest, Primary Ventures, and Next Ventures, and are targeting a January 1, 2027 commercial launch. We're building a company that is deeply trusted by the employers and consultants we serve – and we're looking for our first sales hire to help make that a reality.

The Opportunity You will be among Tokaido's first sales hires, working hand-in-hand with the CEO to expand our footprint in the broker channel. This is a rare chance to shape GTM strategy at a well-funded seed-stage company with a differentiated product in a high priority space.

You will cultivate consultant champions, navigate benefits decision cycles, and close employer groups in partnership with your consultant partners. You'll be in the field operating as an ambassador of the company to tell our story and establish credibility in the market.

What You'll Do

• Own and drive the full sales cycle from first outreach through employer close – prospecting, relationship development, discovery, proposal, negotiation, and contract execution
• Build and activate a network of benefits consultant relationships across regional and national firms targeting middle-market employers (500 – 10,000 employees)
• Partner directly with the CEO on all aspects of go-to-market strategy, pipeline development, and sales execution
• Develop deep fluency in Tokaido's value proposition across infusion navigation, biosimilar substitution, and formulary optimization – and translate that into compelling broker and employer conversations
• Create and maintain a high-integrity pipeline in CRM, with accurate forecasting and deal-stage discipline
• Gather structured market feedback from broker and employer conversations to inform product roadmap and GTM positioning
• Travel regularly to broker offices, industry events, and employer prospect meetings
• Help design repeatable sales processes, playbooks, and materials that will scale as the team grows

What We're Looking For Fit

• Hungry – will grind to build a world class pipeline and stop at nothing to bring a sale over the line
• Humble – genuinely seeks to receive feedback and learn, puts team and customer success ahead of individual credit, and doesn't let personal success override what's best for the customer or the company
• Savvy – Excellent judge of people and circumstances to zero in on actionable opportunities, vocal and opinionated about requirements and what will win the deal, energized by complexity and able to see around corners in a complex market
• Team player – Gracious collaborator beloved by teammates for their deal strategy and preparedness, knows how to deploy internal subject matter experts to maximum effect, embraces winning and losing as a team as opposed to claiming credit

Required

• 10+ years of experience selling employer benefits solutions in the middle market, with a demonstrated record of quota attainment
• Influential in the consultant community with a deep existing network of benefits consultant relationships to call upon
• Proven ability, as evidenced by a winning track record, to successfully execute complex, multi-stakeholder sales through the consultant channel
• Genuine love of prospecting and being in market
• Comfort and enthusiasm for selling at an early-stage company
• Strong communication and presence – able to distill our complex value prop and platform into simple terms that sway senior decision makers

Strongly Preferred

• Experience selling cost containment solutions to benefit leaders
• Familiarity with self-insured employer plan design, stop-loss, TPAs, and the benefits distribution ecosystem
• Existing relationships at regional or national consultant firms such as Alliant, Aon, Gallagher, Holmes Murphy, Hub, Lockton, Mercer, NFP, USI and WTW
• Experience at a seed or Series A company where you built process and playbooks from scratch