Aware Health is on a mission to deliver world-class orthopedic care while helping self-funded employers get their costs under control. We're an AI-powered virtual "orthopedic primary care" company: our clinicians lead the care, and AI makes it more personal, helping people get better faster without going under the knife.
Musculoskeletal (MSK) care is one of the top three cost drivers for health plans and self-funded employers, and half of the U.S. workforce shows up to work in pain. Every benefits leader knows it's a problem, which makes this one of the biggest opportunities in the benefits market. We have the proof: our clients reduce MSK claims costs by an average of 30% per year, and we take on financial risk alongside them. You're never asking a buyer to take a leap of faith. You're showing them the numbers.
We've built a sales engine that works. Brokers bring us back for their next client, our no-stress pilot gets employers to "yes" faster, and our AEs close deals backed by BDRs who generate meetings, a customer success team that activates members, and leadership that wants their input. Now we're scaling, and we're looking for Account Executives who can run a proven playbook in their territory and help make it better, with real ownership of their book, uncapped earning potential, and equity before our next stage of growth.
Location
This role covers our Midwest territory. We prefer candidates based in the Chicago or Milwaukee metro areas. You'll build relationships with the national and regional brokerage offices concentrated there and meet employers across the region in person.
What You'll Do
• Own new business in your territory from first meeting to signed contract, working through brokers, consultants, and directly with self-funded employers
• Partner with dedicated BDRs, one focused on brokers and one on employers, to turn meetings into qualified pipeline you own through close
• Turn broker relationships into repeat business. Most of our wins come from brokers who've already seen us deliver, so the relationships you build will keep paying off
• Run our pilot-to-contract motion: launch employers on a low-risk pilot, use early engagement and outcome data to build the case, and convert the pilot to a signed agreement
• Sell both sides of the B2B2E model: win the employer, then set up the account for strong member activation through a clean handoff to Customer Success
• Navigate pricing conversations, including PEPM and PMPM structures, performance guarantees, and discounting within established guidelines
• Build the Aware brand in your market through LinkedIn, broker events, and in-person meetings
• Keep your pipeline accurate in HubSpot. Your forecast should be something leadership can rely on
• Help shape how we sell as we scale, including messaging, competitive positioning, and process improvements
People Who Do Well Here
• Are critical thinkers who sell consultatively. You diagnose before you prescribe, and you build the business case alongside the buyer
• Are willing to do the work. You build your own pipeline instead of waiting for someone else to do it
• Like figuring out how to scale processes that make the whole team more efficient
• Understand this space, including brokers, consultants, TPAs, and self-funded employers, and can execute quickly
• Have 5+ years of B2B quota-carrying sales experience, ideally in digital health, employee benefits, or a related space
• Have consistently hit or exceeded quota, and can explain how you did it
• Can hold your ground against well-funded competitors without needing to win on price
• Like startup speed and ambiguity, and enjoy working with a team that laughs along the way
• Live in the Midwest region (Illinois or Wisconsin preferred) and travel regularly within the region to meet brokers and clients in person
Compensation & Perks
• $90–120K base salary, uncapped earning potential
• $330–360K OTE
• Accelerators for overperformance
• Quarterly SPIFs and sales competitions
• Ramp plan paid at OTE for hitting ramp goals
• Early equity stake in the company (pre-Series A)
• Medical, dental, and vision plans (PPO, HMO, HDHP options)
• Life and disability insurance, FSA
• Commuter benefits
• 401(k) plan