Sales Lead - Payer​/Health Insurance​/TPAs

About Twenty
30 Health

• Twenty
  30 Health is on a mission to tackle obesity at scale by delivering a clinically rigorous, multimodal care model that integrates medication oversight, lifestyle support, behavioral coaching, and surgical navigation. We partner with health systems, payers, TPAs, brokers, and consultants to improve health while also managing the rising cost of care and medications.
• We’re a nimble, passionate team backed by leading healthcare investors, and we’re building for long-term, system-level change.

10 years of B2B sales experience in the healthcare sales industry—must have sold into or worked within:

• Third Party Administrators (TPAs)
• Employer-sponsored benefits programs
• Broker and consultant channels

• You must have carried a personal sales quota and consistently hit or exceeded targets—this is a hands-on, individual contributor sales role
• Proven track record closing complex, high-value deals—not an account management or sales support role
• Strong relationships and network in the healthcare ecosystem, especially with:

• Payers
• Brokers/Consultants
• TPAs

• We’re seeking a high-performing Sales Representative to help us execute on our go-to-market strategy and close high-value deals with brokers, consultants, TPAs, and health plans. This is a hunter-style sales role focused on sourcing early-stage and advancing late-stage deals, managing inbound interest, and building relationships with key stakeholders to accelerate adoption of our platform.
• You’ll be instrumental in driving tactical execution, including outbound follow-up, meeting prep, sales collateral development and delivery, and proposal coordination. You’ll also work closely with our C-suite, clinical team, and external advisors to bring strategic opportunities across the finish line.

• Own and execute an end-to-end sales process, from prospecting and lead generation to contract negotiation and closing deals—this is a direct sales role with no delegation.
• Own tactical execution across a portfolio of high-priority opportunities (brokers, TPAs, payers, consultants, and aggregators)
• Source new leads, follow up on warm leads, conduct discovery calls, and schedule demos
• Advance deals through the pipeline by delivering proposals, coordinating pilots, and supporting contracting
• Work cross-functionally with product, marketing, and operations teams to provide closed loop feedback on customer needs and ensure seamless onboarding and long-term client success
• Consistently track and report sales activity, pipeline progression, and revenue forecasting in CRM tools (e.g., Hub Spot)
• Support pipeline development by executing targeted outreach campaigns (email, Linked In)
• Stay ahead of market trends, payer challenges, and regulatory changes to proactively adjust sales strategies and strengthen our competitive positioning
• Assist in onboarding and implementation planning for new clients
• Represent the company at industry conferences and networking events to enhance visibility and open doors to new business opportunities

• 10 years of experience in B2B sales–healthcare, benefits, digital health, or insurance preferred
• Strong organizational and follow-up skills; you don’t let balls drop
• Excellent written and verbal communication skills; confident presenting to clients
• A natural relationship builder–you’re approachable, thoughtful, and persuasive
• Experience selling through various channels–direct, benefit brokers/consultants, payers
• Familiarity with CRM tools and outbound platforms like Mailshake or Outreach
• A proven track record of personally closing large, complex, multimillion-dollar deals—this is not a leadership or oversight role.
• Strong existing relationships and network within health plans, brokers, TPAs, employer groups, and other payer entities.
• Experience developing innovative pricing and pilot strategies to help drive growth
• Self-motivated, hands-on, and thrives in a high-growth, high-performance sales environment.
• Ability to build presentations (PPT etc.) to articulate clinical and financial value propositions to payer decision-makers with credibility and impact.

• Experience working in a startup or fast-paced, high-growth environment a plus
• Understanding of obesity, metabolic health, or GLP-1s and their impact on employer healthcare costs
• Prior involvement in employer-sponsored benefit solutions or digital health platforms

• Mission-driven work that makes a tangible difference in people’s lives
• A collaborative and entrepreneurial team environment
• Ground-floor opportunity to grow with a company tackling one of the most urgent healthcare challenges of our time
• Competitive compensation offering high commission percentage and generous benefits package