Regional Sales Director for Michigan​/Illinois and Upper Midwest – Connected Vehicle​/Telematics Solutions

Locations: Michigan / Illinois and Upper Midwest
Reports To: Vice President Sales
Travel: Minimum 4 days per week in the field (franchise dealerships)

Guidepoint Systems is a leader in connected vehicle and telematics solutions designed to help dealerships protect their inventory, improve service operations, and enhance customer satisfaction. Our EVTS (Electronic Vehicle Tracking System) platform provides real-time vehicle visibility, battery health management, and customer engagement tools that drive both dealership efficiency and profitability.

We’re looking for a driven, self-starting Regional Sales Director with a proven track record of winning new B2B business within franchise automotive dealerships or the telematics space. This is a hunter role — focused on net-new account acquisition. You will be on the phone and in the field, prospecting and cold calling franchised automotive dealerships to introduce them to Guidepoint’s industry‑leading connected vehicle and telematics solutions.

Guidepoint holds OEM‑approved partner statue with Stellantis, giving our reps a warm point of entry and added credibility when calling on franchised dealerships. Dealers retain the final buying decision, but program alignment opens doors that cold calling outreach alone can’t – and you’ll walk into those conversations with OEM‑backed credibility that competitors simply can’t match.

• Build your book of business through daily cold calls, in‑person dealership visits, email, video, and text outreach. Strategic partnerships and OEM programs provide a warmer introduction.
• Deliver a sharp, compelling value proposition in under 60 seconds.
• Turn cold introductions into qualified opportunities.
• Run disciplined discovery and position solutions through consultative, value‑based selling.
• Manage multiple opportunities simultaneously and move them intentionally through each sales stage.
• Close new business consistently and predictably.

• Thick skin and short memory — rejection fuels you.
• High activity levels and personal accountability for pipeline creation.
• Strong executive presence and the ability to command attention quickly.
• Exceptional communication skills across in‑person meetings, video conferences, phone, and written outreach.
• A competitive drive to outperform peers and exceed targets.

• Top performers who don’t wait for opportunity — they create it.
• Professionals who measure success in closed‑won revenue.
• Sales leaders who take pride in outworking and outexecuting the competition.

If you are motivated by building something, winning new business, and being rewarded for performance — this is the role for you.

• Relentless prospecting activity and consistent new opportunity creation.
• Strong pipeline management with disciplined follow‑up
• Clear, persuasive communication across in‑person meetings, video calls, phone conversations, emails, and text
• A competitive mindset with the persistence to win in a highly competitive environment

This role is ideal for a driven, self‑motivated sales professional who takes pride in opening doors, creating opportunities where none existed, and closing new business.

• 3–5 years of B2B new business sales experience with a successful track record of exceeding targets.
• Experience hunter in the automotive dealerships space or within the telematics / connected vehicle industry strongly preferred.
• Strong understanding of dealership operations, particularly F&I, sales, and service workflows.
• Proven ability to build executive‑level relationships and close complex sales cycles.
• Self‑motivated with strong organizational and territory management skills.
• Excellent prospecting, communication, presentation,…