Regional Director, Mid-Market Sales

23 hours, 58 minutes ago
Full-time
Lead
Sales and Business Development
Thatch

Thatch

Thatch is a health benefits platform that combines financial technology and insurance services. Founded in October 2021 by Chris Ellis and Adam Stevenson, the company is based in San Francisco, with additional offices in New York and Austin. Thatch's mission is to decouple health insurance from employment, allowing businesses to offer personalized healthcare experiences to their employees. The platform serves as a Third-Party Administrator (TPA) and specializes in Individual Coverage Health Reimbursement Arrangements (ICHRA). Thatch simplifies health benefits administration by enabling employers to set tax-free healthcare budgets, which employees can use to select their own health insurance plans and additional benefits like mental health support and wellness programs. The company also provides a Visa debit card for employees to manage their healthcare spending easily. Thatch primarily targets small to mid-sized businesses and startups, offering a streamlined setup process and tools to help employers manage healthcare budgets effectively. With significant investor backing, Thatch is positioned to enhance the healthcare experience for businesses and their teams.

information technology & services
51-200
Founded 2021
$84M raised

Description

  • Own and deliver the regional ARR target through a team of Mid-Market Account Executives.
  • Maintain a high-quality pipeline across the region with strong coverage, velocity, and deal progression.
  • Forecast revenue accurately and communicate risks and upside clearly.
  • Hire, onboard, and ramp Mid-Market AEs across the East Coast region.
  • Coach reps on discovery, deal strategy, objection handling, and executive-level selling.
  • Run regular 1:1s, pipeline reviews, deal reviews, and forecast calls.
  • Support AEs on complex, multi-stakeholder sales cycles and broker-influenced deals.
  • Act as an escalation point for strategic deals, key accounts, and broker relationships.
  • Partner with Solutions Engineering, Implementation, Product, Marketing, and Leadership to unblock deals and improve the sales motion.
  • Develop and execute a regional plan for broker coverage, pipeline generation, and strategic account targeting.

Requirements

  • 7+ years of experience managing and scaling quota-carrying sales teams.
  • Experience owning a regional or segment number and forecasting accurately.
  • Background in SaaS, healthcare, insurance, HR tech, or similar complex B2B sales environments.
  • Strong understanding of consultative, multi-stakeholder sales cycles.
  • Experience working with or through broker or channel-led motions (preferred).
  • Coach-first mindset with the ability to elevate rep performance through feedback and accountability.
  • Operational rigor in pipeline management, forecasting, and execution.
  • Ownership mentality and strong accountability for outcomes.
  • Strategic thinking with the ability to plan at the regional level and win individual deals.
  • High standards for talent and thoughtful hiring practices.

Benefits

  • Estimated compensation range of $250,000 to $300,000 USD OTE.
  • Fully distributed work environment.
  • Opportunity to join an early-stage company.
  • Fast-moving, high-velocity team environment.
  • Interview process with live case study and direct access to founders.

Interested in this position?

Apply directly on the company website

Apply Now

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