Account Executive - Mid Market, Central

About Thatch

For most people, health insurance is something that happens to them: a plan chosen by someone else, with little room to fit their life. Thatch is changing that. We help companies give every employee a real healthcare budget instead of a one-size-fits-all plan, so people can choose the coverage and care that works for them, and employers get predictable costs they can control.

It’s a simple idea, but making it real means solving hard problems across healthcare, payments, and technology, and we’re just getting started. We look for people who like solving complex problems, use good judgment, and are comfortable working through ambiguity. People here care deeply about our customers, take real responsibility for what gets built, and are driven by doing work that matters.

About the role

We’re looking for a consultative, strategic Account Executive to join our Mid-Market sales team at Thatch, owning a market within our Central territory. Alongside our Broker partners, you will work with HR, finance, and executive stakeholders at companies with 100+ employees to solve complex healthcare challenges. This is an ideal role for someone who can run an exceptional sales process, influence high-level decisions, and help us build a category-defining business.

Where this role is based

This role covers the Central territory. You’ll own the market where you live. We’re prioritizing candidates who are based in, and well networked in, the market they’d cover. We’re hiring reps who live in, and already have broker relationships in the following markets: Minneapolis–St. Paul, Chicago, Dallas–Fort Worth, Austin, Houston, Kansas City

Please apply to only one territory job post (East, Central, West): the one that includes your market. 

What you'll do

• Lead high-stakes consultative sales processes with companies navigating complex benefits needs across your assigned territory.
• Act as a trusted advisor to executive-level buyers in your market, uncovering deep needs and aligning them to Thatch’s solutions.
• Work cross functionally with product teams to refine positioning for this segment.
• Analyze and share insights on the competitive landscape in your market, influencing go-to-market strategy.
• Drive forecasting accuracy and pipeline health for the regional territory through disciplined sales operations.
• Build relationships with existing and new broker partners across your market.
• Travel within your assigned territory to build relationships and support broker partners.

Background we're looking for

• 3+ years of experience in group benefits mid-market consulting, specifically tier 1 or tier 2 brokerage firm background, healthcare carrier field representation, payroll sales, or HR tech / SaaS sales is a requirement.
• An established network of brokers and benefits professionals in your market, and a clear plan for where you’d prospect first.
• Strong working knowledge of group medical plans: you can read SBCs, analyze a group’s current benefits, and support quoting. You also understand the basics of underwriting, including plan design, contribution strategies, and key cost and risk drivers.
• Skilled at leading discovery, building business cases, and influencing multiple stakeholders across finance, HR, and executive teams.

Experience we’d be particularly excited about

• You’ve built a book of business from scratch and enjoy outbound prospecting.
• Inquisitive and thoughtful — you know how to ask the right questions and listen deeply
• Passionate about creating a healthcare system that people will love.
• Comfortable managing long and potentially very quick sales cycles and adapting to shifting priorities in a fast-paced environment.
• Someone who consistently embodies the Thatch brand and effectively represents our broker partners and clients.

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, your market, and your interest in Thatch
• 30 minute video meeting with the hiring manager to dive deeper into your sales experience, your broker network, and how you’d build a book in your market
• 30 minute video meeting to meet 2 members of our sales team to discuss your market knowledge, sales approach, and how you’d operate at Thatch
• 30 minute working session with the hiring manager to go over a practical assessment focused on a real scenario you’d see in this role. We’ll share details ahead of time
• 30 minute video meeting with the department head about the mid-market motion and your approach to building a territory
• 30 minute video meeting with one of 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.