Thatch (thatch.ai) Logo

Thatch (thatch.ai)

Regional Director, Mid-Market Sales

Posted One Month Ago
Remote
Hiring Remotely in US
250K-300K Annually
Senior level
Remote
Hiring Remotely in US
250K-300K Annually
Senior level
Lead and scale a Mid-Market East sales team to hit multi‑million ARR. Own regional revenue, forecasting, pipeline health, hiring and coaching AEs, manage complex consultative deals and broker relationships, ensure clean handoffs to implementation and CS, and partner cross‑functionally to drive GTM and regional strategy.
The summary above was generated by AI
About the role

We’re hiring a Regional Director, Mid-Market West to build, lead, and scale a team of Account Executives across the West Coast Region. This leader will own regional revenue outcomes, coach AEs through complex consultative sales cycles, and act as the connective tissue between Sales, Brokers, Solutions, Implementation, and Product.

This role is ideal for a high performing sales professional who has led sales teams in ambiguous, category-creating environments and knows how to translate strategy into repeatable execution. You will be accountable for hitting a multi-million ARR target, building strong broker relationships in your region, and developing AEs into consistent top performers.

What you'll doOwn Regional Revenue & Forecasting
  • Own and deliver the regional ARR target through a team of Mid-Market AEs.
  • Maintain a high-quality pipeline across the region, ensuring coverage, velocity, and deal progression.
  • Forecast accurately and communicate risks and upside clearly.
Build & Coach a High-Performing Team
  • Hire, onboard, and ramp Mid-Market AEs across the West 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 with rigor and consistency.
  • Raise the bar on sales methodology, discipline, and accountability across the team.
Drive Complex, Consultative Sales Execution
  • Support AEs on complex deals involving multiple stakeholders, longer sales cycles, and broker-influenced motions.
  • Act as an escalation point for strategic deals, key accounts, and broker relationships.
  • Ensure clean handoffs from Sales → Implementation and long-term customer success.
Partner Cross-Functionally
  • Work closely with Solutions Engineering, Implementation, Product, Marketing, and Leadership to unblock deals and improve the sales motion.
  • Share regional learnings and field insights to influence product, pricing, and GTM strategy.
  • Align broker strategy, enablement, and incentives with regional goals.
Build the Region
  • Develop and execute a regional plan that includes broker coverage, pipeline generation, and strategic account targeting.
  • Represent Thatch externally with brokers, partners, and senior customer stakeholders.
  • Travel as needed to support reps, brokers, and key opportunities.
Background we're looking for
  • 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 adjacent complex B2B sales environments.
  • Strong understanding of consultative, multi-stakeholder sales cycles.
Leadership Attributes
  • Coach-first mindset: You elevate rep performance through clarity, feedback, and accountability.
  • Operational rigor: You run clean pipelines, disciplined forecasts, and tight execution.
  • Ownership mentality: You take responsibility for outcomes.
  • Strategic thinking: You can zoom out to plan a region and zoom in to win a deal.
  • High bar for talent: You hire thoughtfully and don’t compromise on quality.
Experience we’d be particularly excited about
  • Experience working with or through broker / channel-led motions.
What to expect

We interview rigorously based on integrity, talent, and drive; the trust we display in our teammates from day 1 is a reflection of the confidence we have in this process. We aim to evaluate the things you’ll be doing every day as best we can, and we move quickly. Here's what to expect:

  • 30 minute video meeting to talk through your background and interest in Thatch
  • 30 minute video meeting with the hiring manager to dive deeper into your experience and the role
  • 30 minute video meeting to meet 4 members of the team
  • 30 minute video meeting to work through a live case study
  • 30 minute video meeting with our founders to discuss your approach to culture and our operating principles

Please note: The posted compensation range reflects On-Target Earnings (OTE), not base salary.

Estimated Compensation Range
$250,000$300,000 USD
 
About Thatch

We’re a fully distributed early stage company using technology to change the way America does healthcare. We’re a happy, friendly, high-velocity team. You can read more on Thatch here.

Similar Jobs

An Hour Ago
Remote or Hybrid
45K-85K Annually
Junior
45K-85K Annually
Junior
Artificial Intelligence • Fintech • Insurance • Marketing Tech • Software • Analytics
Handle inbound calls and warm leads, assess customers’ insurance needs, recommend appropriate Property and Casualty products and coverages, and convert prospects into policyholders. The role includes paid training and licensing, customer communication, sales closing, and representing the Liberty Mutual brand. Employees work remotely on a fixed schedule, must obtain a Property and Casualty license after hire, and meet specified home-office and internet requirements.
Top Skills: PcWired High-Speed Internet
An Hour Ago
Remote or Hybrid
45K-100K Annually
Junior
45K-100K Annually
Junior
Artificial Intelligence • Fintech • Insurance • Marketing Tech • Software • Analytics
Handles inbound calls and warm leads to assess customers’ insurance needs, recommend appropriate Property and Casualty products, and convert prospects into policyholders. The role includes paid licensing and sales training, customer consultation, lead conversion, and maintaining strong service standards. Representatives work remotely on assigned schedules, use provided equipment, and must meet home-office internet requirements. A Property and Casualty license is required after hire.
Top Skills: Cable InternetDsl InternetFiber InternetPc
Yesterday
Remote or Hybrid
45K-85K Annually
Junior
45K-85K Annually
Junior
Artificial Intelligence • Fintech • Insurance • Marketing Tech • Software • Analytics
Handles inbound calls and warm leads to understand customers’ insurance needs, recommend appropriate Property & Casualty products and coverages, and convert prospects into policyholders. The role includes paid training and licensing, customer consultation, sales closing, brand representation, and remote collaboration. Employees must work a fixed schedule including one weekend day, maintain a compliant home office and wired high-speed internet, and remain in their resident state for at least one year.
Top Skills: PcWired High-Speed Internet

What you need to know about the Chicago Tech Scene

With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.

Key Facts About Chicago Tech

  • Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
  • Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
  • Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
  • Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
  • Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
  • Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory

Sign up now Access later

Create Free Account

Please log in or sign up to report this job.

Create Free Account