Upper Midwest and Remote field sales

Auto Engage is an AI communication platform built for franchised dealership groups, with a focus on the service side of the business: customer communication, retention, repair order growth, and fixed-ops revenue.

Our product is already running at national scale, including across every store for two of the five largest dealer groups. We are now expanding our field sales team and hiring a Regional Sales Manager to own our Upper Midwest territory, covering Illinois, Wisconsin, Minnesota, and Iowa.

This is a remote field sales role with a flexible schedule and regular territory travel. Candidates should live in or near the territory and be comfortable traveling throughout Illinois, Wisconsin, Minnesota, and Iowa, including overnight travel for dealership visits, group meetings, route-based prospecting, and quarterly trade shows or industry events as required.

This role is for someone who already knows automotive retail.

We are not looking to teach you how dealerships work. You should be comfortable walking into a dealership, understanding the store, identifying the decision-makers, and having a business conversation with service directors, fixed-ops directors, general managers, dealer principals, and group-level operators.

You will own a regional territory, build pipeline, run discovery, lead demos, and close new business. This is a role for a self-starter who does not need to be handed a daily playbook, a warmed-up pipeline, or constant direction.

You will report directly to the Director of Revenue and work closely with BDRs, leadership, and implementation/customer teams as opportunities move from first conversation to closed business.

• Own new business development across Illinois, Wisconsin, Minnesota, and Iowa.
• Prospect franchised dealerships and dealer groups through field visits, phone, email, Linked In, 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 Hub Spot.
• Represent Auto Engage 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.

The core requirement is sales experience in the automotive retail world. You should already understand dealership operations, dealership politics, and how decisions get made inside stores and groups.

• 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.

• Experience as a high-performing automotive vendor rep, dealership technology rep, fixed-ops consultant, or dealer-group operator with strong commercial instincts.
• Dealership management experience paired with real sales ability and comfort prospecting.

• You know who the real decision-makers are inside a dealership.
• You can walk into a store and quickly understand the people, politics, and opportunity.
• You are comfortable creating pipeline through your own activity, relationships, and field presence.
• You can run a professional sales process without needing to be micromanaged.
• You are comfortable being measured on pipeline created, demos completed, rooftops closed, and revenue generated.
• You can balance field selling, CRM discipline, forecasting, and consistent follow-up.

• You need a heavily managed sales environment.
• You are looking for mostly inbound leads.
• You are uncomfortable with prospecting, overnight travel, or walking into dealerships.
• You prefer account management over hunting for new business.

• Hub Spot for account management, opportunity tracking, activity records, forecasting, and pipeline visibility.
• Linked In,…