Account Executive - Small & Medium Business (SMB)

About the role

We’re hiring a driven and adaptable Account Executive to join our SMB segment. 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.

What you'll do

• 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.

Background we're looking for

• 3–5 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.

Experience we’d be particularly excited about

• 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.

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:

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