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.
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.
- 3–5+ years in a SaaS sales role, ideally across both transactional and strategic motions.
- 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.
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 — the entire interview process is typically complete within 2 weeks. We will conduct the following interviews:
- 30 minute Zoom meeting to talk about Thatch, your background, and answer any questions about the role.
- 45 minute Zoom meeting to hear more about your experience and how you'd approach working in the role.
- Three 30 minute zooms with additional Thatch teammates to access your skill sets.
- Take home project to assess your functional expertise for the role you're applying for and a 30 minute meeting to review the assignment.
- 30 minute Zoom meeting with our founders to discuss your approach to culture and our operating principles.
- Final 30 minute call to answer any outstanding questions.
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.
Top Skills
Similar Jobs
What you need to know about the Chicago Tech Scene
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