Account Executive - Enterprise, National

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 an exceptional Enterprise Account Executive, National Accounts to help establish and scale Thatch's enterprise business nationally.

This is a strategic, hands-on sales role for someone who understands employer-sponsored healthcare, knows how to navigate complex enterprise purchasing decisions, and has experience working with leading national benefits consulting firms, including Mercer, Aon, WTW, Lockton, and Gallagher.

Success requires more than traditional enterprise sales experience. You must understand how large employers evaluate healthcare strategies, how consultants influence those decisions, and how to effectively engage both audiences. You know when to sell directly, when to engage consulting partners, and how to maintain ownership of the sales process.

You'll report to our VP of Revenue and regularly engage with Thatch's founders and executive leadership team on strategic opportunities, partnerships, and enterprise growth.

This is the first of several planned enterprise sales hires. We're looking for a proven individual contributor who is equally excited about helping build the strategy, playbook, and team we'll develop over the next two years. For the right person, this role offers meaningful opportunities for future leadership.

What you'll do

Drive National Enterprise Growth

• Build and own a national pipeline of large employer opportunities.
• Lead complex sales cycles from prospecting through contracting.
• Develop relationships with CHROs, CFOs, benefits leaders, and executive decision-makers.
• Build compelling financial and strategic business cases for Thatch.
• Navigate enterprise procurement, RFPs, legal reviews, and multistakeholder decisions.
• Deliver consistent sales performance, pipeline discipline, and accurate forecasts.

Develop Strategic Consulting Relationships

• Build relationships with Mercer, Aon, WTW, Lockton, Gallagher, and other leading consulting firms.
• Understand consultant influence, RFP processes, and employer decision-making.
• Generate opportunities through both direct employer engagement and consulting partnerships.
• Maintain direct employer relationships while working collaboratively with consultants.
• Position Thatch as a credible alternative to traditional employer-sponsored healthcare.

Bring Deep Healthcare Expertise

• Translate complex healthcare financing and benefits strategies into executive-level conversations.
• Understand fully insured, self-funded, and alternative employer healthcare models.
• Engage employers on healthcare costs, financial risk, plan design, and employee experience.
• Partner with internal finance, product, carrier, and operations teams to develop solutions.
• Guide employers and consultants through the evaluation of ICHRA and emerging healthcare models.

Help Build Our Enterprise Business

• Partner with the VP of Revenue to shape enterprise sales strategy and execution.
• Help establish target account strategies, sales processes, and consulting engagement models.
• Provide market feedback to inform product development and enterprise positioning.
• Contribute to hiring, mentoring, and developing future enterprise sellers.
• Remain accountable for individual sales performance while helping scale the organization.

Background we're looking for

Required Experience

• 5–7+ years of enterprise sales experience in employer-sponsored healthcare, insurance, or benefits solutions.
• Proven success originating and closing complex, high-value enterprise opportunities.
• Experience in one or more of the following:
• Health insurance carriers, particularly national accounts or large group.
• Third-party administrators (TPAs) or self-funded benefits administration.
• Employer benefits consulting or healthcare advisory services.
• Healthcare benefits technology and solutions, including navigation, cost management, and care delivery.
• Experience working with national consulting firms and understanding their role in employer purchasing decisions.
• Demonstrated ability to sell directly to employers and alongside consulting partners.
• Strong understanding of enterprise procurement, RFPs, contracting, and executive decision processes.
• Established credibility with senior HR, finance, and executive stakeholders.
• Strong financial acumen, executive communication, and negotiation skills.
• Willingness to travel nationally.

Experience We'd Be Especially Excited About

• Deep self-funded healthcare expertise, including ASO, stop-loss, claims experience, network strategies, and renewal economics.
• Established relationships with national benefits consultants and large employer decision-makers.
• Experience selling innovative healthcare solutions that challenge traditional insurance models.
• Familiarity with ICHRA, defined contribution benefits, or alternative healthcare financing.
• Success creating direct employer demand rather than relying exclusively on consultant referrals.
• Experience building a new market, enterprise sales motion, or go-to-market strategy.
• Interest in mentoring sellers and potentially leading an enterprise team as Thatch grows.

Who Thrives in This Role

You're a builder. You want to create an enterprise business, not simply inherit a territory and established playbook.

You understand healthcare. You know how employers, consultants, carriers, and administrators interact, and you're comfortable discussing the economics of self-funded healthcare.

You can sell directly and through partners. You value consulting relationships but know how to create demand and develop executive relationships independently.

You can sell change. You're comfortable challenging conventional thinking and guiding sophisticated employers through consequential healthcare decisions.

You operate at the executive level. You can engage a CFO on healthcare economics, a CHRO on workforce strategy, and a consultant on benefits design.

You have an ownership mentality. You're resourceful, accountable, and energized by building something new.

You want to grow. You're motivated by individual success today and the opportunity to help build and potentially lead a national enterprise sales team tomorrow.

Why Thatch

Enterprise healthcare is at an inflection point. Employers are looking for alternatives to traditional approaches that have delivered rising costs, limited flexibility, and increasingly complex benefits experiences. 

Thatch is positioned to help lead that transformation.

You'll have the opportunity to work directly with our founders and executive team, shape our national enterprise strategy, influence product development, and help build a business with significant growth potential.

We're looking for someone who wants to win meaningful enterprise business today and help build the organization that will define our growth tomorrow.

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
• 30-45 minute video meeting with the hiring manager to get a high level understanding of your experience and deep into your sales experience
• 30 minute video meeting to meet 3 members of the team
• 30 minute video meeting to go over a case study assignment
• 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