Regional Sales Director for Michigan / Illinois and Upper Midwest

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

About Guidepoint Systems

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.

About This Role

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.

What You’ll Do:

• 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.

What It Takes:

• 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.

Who Thrives Here:

• 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.

What Success Looks Like:

• 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.

Qualifications

• 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, and negotiation abilities.
• Strong problem solving, analytical, and organizational abilities.
• Comfortable balancing multiple priorities and account in a fast-paced environment.
• Proficiency in CRM systems and Microsoft Office suite.
• Valid driver’s license and ability to travel extensively within the assigned territory.

What We Offer

• Competitive base salary plus uncapped commissions.
• Mileage reimbursement and travel expense allowance.
• Full training, product support, and marketing resources.
• Opportunity to represent a trusted, industry-leading telematics solution with significant growth potential.
• A collaborative, performance-driven culture with advancement opportunities.

Join the Guidepoint Team

If you’re a motivated, new business-focused sales professional with dealership or telematics experience, we invite you to join a growing company at the forefront of connected vehicle technology.
Apply today and help dealerships turn vehicle data into profit.