Enterprise Account Executive

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.