[Hiring] Regional Sales Manager @Carrum Health

Role Description

We are looking for a Mid-Market Account Executive to help us accelerate our growth across self-insured employers with 5,000 and fewer covered lives. The Mid-Market Account Executive will play a critical role in our success.

Reporting to the VP of Sales, you will own the full sales cycle for mid-market employer accounts and be crucial in expanding Carrum Health’s footprint with key regional brokers and consultants; helping us ensure that our value-based surgical and cancer care solutions reach employers seeking immediate, impactful healthcare cost savings. You’ll be responsible for:

• Driving new ARR.
• Building and qualifying a strong pipeline.
• Running high-impact product presentations.
• Closing deals in a fast-paced environment.

You’re excited about this opportunity because you will...

• Own the end-to-end sales strategy and revenue execution for accounts with up to 5,000 lives within your assigned territory.
• Help build repeatable mid-market sales playbooks and strong regional broker channel partnerships to fuel ongoing pipeline growth.
• Regularly collaborate with Solutions Consultants, Customer Success, Marketing, and our Partnerships team to deliver compelling, custom ROI proposals for prospective employers.
• Run high-velocity multi-stakeholder deals, engaging HR leaders, Total Rewards Directors, CFOs, and benefit consultants.
• Serve as a market feedback conduit to help influence product messaging and solution design for the mid-market segment.

Qualifications

• Rich background of B2B sales success in digital health, benefits tech, or healthcare cost-containment solutions.
• Strong skills working with regional benefits brokers, and national consulting firms (e.g., Mercer, WTW, Aon, Lockton, Gallagher) to drive co-selling opportunities.
• 3–5+ years of full-cycle B2B sales experience, digital health, benefits tech, or healthcare SaaS company preferred.
• Experience in selling directly to HR Executives, VPs of Total Rewards/Benefits, and CFOs within self-funded employer models.
• Track record in consistently exceeding annual quotas (100%+ to target) in competitive sales environments.
• Ability to translate complex value-based care models, stop-loss mechanics, and healthcare ROI data into clear, actionable business cases for buyers.
• Ability to thrive in a fast-paced, high-growth environment with strong self-starter initiative and pipeline-building discipline.
• Entrepreneurial and resourceful — you’re a problem solver.
• Experience handling deadlines, keeping many balls in the air, and prioritizing work in a fast-paced, dynamic environment.
• Passion for collaborating cross-functionally with sales, operations, client success, data, and product teams to ideate, complete projects, and drive impactful results.

Benefits

• Stock option plan and performance bonus for eligible employees.
• Flexible schedules and remote work.
• Chicago and San Francisco offices available as an option.
• Flexible PTO, within reason.
• Summer Fridays (sign off @ 1pm local time).
• 15+ paid holidays, including Juneteenth, World Mental Health Day, and Carrum Health Day.
• Annual holiday shutdown in December.
• Paid parental leave.
• Health, vision, and dental insurance.
• Employee Assistance Programs (EAP).
• 401K retirement plan.