Account Executive

Aware Health Labs Inc•Chicago, IL

2h•$90,000 - $120,000

About The Position

Aware Health is an AI-powered virtual orthopedic primary care company working to deliver orthopedic care while helping self-funded employers control costs. The Account Executive owns new business across the Midwest territory, working with brokers, consultants, and self-funded employers. The role runs a pilot-to-contract sales motion, develops broker relationships that generate repeat business, and partners with BDRs and Customer Success to take opportunities from meeting through close and member activation. The Account Executive also helps improve the sales playbook as the company scales. The territory is the Midwest, with a preference for candidates in the Chicago or Milwaukee metro areas. The role involves building relationships with national and regional brokerage offices and meeting employers across the region in person. Regular regional travel is expected.

Requirements

At least 5 years of B2B quota-carrying sales experience.
Consistent history of meeting or exceeding quota and ability to explain how results were achieved.
Understanding of brokers, consultants, TPAs, and self-funded employers.
Critical thinking and consultative selling skills, including diagnosing customer needs and building the business case with buyers.
Ability to build pipeline proactively.
Ability to compete against well-funded competitors without relying on price.
Comfort with startup speed and ambiguity.
Residence in the Midwest region; Illinois or Wisconsin preferred.
Willingness to travel regularly within the region.

Nice To Haves

Experience in digital health, employee benefits, or a related space.
Residence in the Chicago or Milwaukee metro areas.

Responsibilities

Own new business in the territory from first meeting through signed contract, working through brokers, consultants, and directly with self-funded employers.
Partner with dedicated BDRs focused on brokers and employers to develop qualified pipeline and own opportunities through close.
Build broker relationships that generate repeat business.
Run the pilot-to-contract sales motion, using early engagement and outcome data to support conversion to a signed agreement.
Win employer business and hand off accounts to Customer Success for member activation.
Navigate pricing conversations involving PEPM and PMPM structures, performance guarantees, and discounting within established guidelines.
Build the Aware brand in the market through LinkedIn, broker events, and in-person meetings.
Maintain accurate pipeline information in HubSpot and provide a reliable forecast to leadership.
Help shape sales messaging, competitive positioning, and process improvements as the company scales.
Travel regularly within the Midwest region to meet brokers and clients in person.