Enterprise Account Executive

Executive Integrity | B Corp®; Chicago (IL); Hybrid; USD 300,000 - 700,000; Full time

Benefits offered by this job

Base + uncapped commission

Accelerators for big wins

Stock options

Liquidity-event payout

Job summary

Executive Integrity in Chicago is seeking an experienced Enterprise Account Executive to own the Midwest territory for an AI-powered supply chain visibility platform. The role covers from Chicago outward to Milwaukee, the Twin Cities and St.

Louis, with a proven track record of enterprise success. You will close $250k+ transformation deals with VP and C-suite buyers, manage a live pipeline, and help shape the regional go-to-market plan with the RVP/SVP of Sales.

Qualifications

• 7+ years carrying an enterprise quota with consistent attainment.
• Deep transportation or TMS domain knowledge.
• Hunter who builds and runs a territory plan without a large enablement team.
• Polished, prepared and data-led with measurable results.
• Tenure showing a history of success, not frequent moves.

Responsibilities

• Own Midwest territory end to end from Chicago to Milwaukee, the Twin Cities and St. Louis.
• Close $250k+ transformation deals with VP and C-suite buyers.
• Convert a live pipeline of near-close installs while opening net-new logos.
• Shape the go-to-market plan for the region with the RVP and SVP of Sales.

Skills

Enterprise sales

Territory planning

Data-led selling

Negotiation

Close deals

Job description

Job Title: Enterprise Account Executive Location: Chicago Metro (hybrid) Preferred

The Opportunity

A leading supply chain visibility and AI platform needs a proven enterprise seller to own its Midwest patch. The leadership team has been clear: this seat goes to an adult in the room, a seasoned seller with a record of repeated wins, not a first-time enterprise rep. The territory comes with an existing book, installs close to the line and prospects already engaged.

The Impact You Will Have

• Own a Midwest territory of enterprise shippers end to end, from Chicago out to Milwaukee, the Twin Cities and St. Louis
• Close $250k+ transformation deals with VP and C-suite supply chain, transportation and IT buyers
• Convert a live pipeline of near-close installs while opening net-new logos
• Shape the go-to-market plan for the region with the RVP and SVP of Sales

What Success Looks Like

• 7+ years carrying an enterprise quota, with sustained attainment year on year
• Deep transportation or TMS domain knowledge, able to hold a room of 25-year industry lifers
• A hunter who builds and runs a territory plan without a large enablement team behind them
• Polished, prepared and data-led, with numbers that actually land
• Tenure that tells a story of success, not movement

What Is on Offer

• Competitive base with a 50/50 split, uncapped commission
• Accelerators that reward big wins, including a seven-figure bonus on the largest deals
• Stock options plus a cash plan that pays out on a liquidity event
• A draw to keep you whole while you ramp, and a lean team where individual output is seen

If you are already succeeding and want a bigger number on a sharper platform, we would like a confidential conversation.

Who are we?

Executive Integrity is a global executive search and recruitment consultancy for a more sustainable world with a focus on talent within the Maritime and Renewable Energy sectors. We give a proportion of all our profits to Renewable World, a charity that develops affordable and innovative renewable energy solutions to poverty-stricken communities.