Remote Regional Automotive AI Sales – Upper Midwest

Autoengage.ai; Chicago (IL); On-site; USD 170,000 - 190,000; Full time

Benefits offered by this job

Medical, dental, and vision

Paid time off

Paid company holidays

Job summary

AutoEngage is seeking a Regional Sales Manager to own the Upper Midwest territory (IL, WI, MN, IA) with a remote field sales model and regular travel. You’ll build pipeline, run discovery, lead product demos, and close new business with franchised dealer groups.

Ideal candidates have automotive retail sales experience, existing dealership relationships, and a proven ability to independently generate and manage pipeline, demos, and revenue.

Qualifications

• Experience selling software, technology, marketing, communications, fixed‑ops, BDC, CRM, DMS‑adjacent, or service‑lane solutions into franchised dealerships or dealer groups.
• Existing relationships with dealership operators, fixed‑ops leaders, dealer principals, or automotive group executives.
• Proven ability to generate your own pipeline, manage a territory, run demos, and close business.

Responsibilities

• Own new business development across Illinois, Wisconsin, Minnesota, and Iowa.
• Prospect franchised dealerships and dealer groups through field visits, phone, email, LinkedIn, referrals, events, and industry relationships.
• Build relationships with service directors, fixed‑ops directors, general managers, dealer principals, and group executives.
• Run discovery conversations and product demos focused on service communication, retention, RO growth, and revenue outcomes.
• Build and manage a territory plan, including priority accounts, travel routes, dealer‑group opportunities, and follow‑up strategy.
• Work with BDRs to convert qualified meetings into real pipeline and closed business.
• Maintain accurate account, opportunity, activity, and forecast records in HubSpot.
• Represent AutoEngage professionally in dealerships, at quarterly trade shows or industry events, and with dealer‑group leadership.
• Share market feedback with leadership as we expand our field sales motion.

Job description

AutoEngage is seeking a Regional Sales Manager to own the Upper Midwest territory (IL, WI, MN, IA) with a remote field sales model and regular travel. You’ll build pipeline, run discovery, lead product demos, and close new business with franchised dealer groups.

Ideal candidates have automotive retail sales experience, existing dealership relationships, and a proven ability to independently generate and manage pipeline, demos, and revenue.