Account Executive - Small and Medium Business (SMB)

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.

We’re hiring a driven and adaptable Account Executive to join our SMB segment at Thatch. In this role, you’ll engage with growing businesses navigating healthcare benefits for the first time — blending both transactional hustle and strategic guidance. You’ll work cross-functionally, communicate clearly, and help us build the systems that power repeatable success in this space.

• →Manage a hybrid sales motion, balancing fast-moving transactional deals with larger, compliance-involved opportunities.
• →Engage key stakeholders and educate them on Thatch’s healthcare solutions.
• →Tailor pitches to a mix of technical and non-technical buyers across various industries.
• →Work closely with product, growth, and customer success to iterate and improve the SMB sales playbook.
• →Track pipeline metrics rigorously and proactively report on trends and forecasts.
• →Travel occasionally for team on-sites or key customer meetings, typically under 20 percent.

• 1-3 years of proven sales experience in group insurance, payroll services, or ICHRA solutions
• Strong communicator who can adjust style based on audience — from HR leaders to CFOs.
• Comfortable operating in ambiguity and navigating compliance-heavy conversations.

• Thrives in a startup environment and excited about building process from the ground up.
• Experience with benefits, HR tech, or compliance-related sales is a bonus.
• Combination of payroll and group insurance experience.
• Fluency in Spanish is a plus.

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 2-3 members of the team
• 30 minute video meeting to go over a case study assignment
• 30 minute video meeting with our Sales Leadership and one of our Co-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.