Regional Sales Manager - DealerPay (Great Lakes Region)

Regional Sales Manager

Dealer Pay is a dealer-focused embedded finance solution provider dedicated to delivering secure, efficient, and tailored payments and finance solutions for automotive dealerships. With over 20 years of industry experience, Dealer Pay specializes in streamlining payment acceptance across all dealership departments, including sales, service, parts, and F&I. Our comprehensive suite of services encompasses credit card processing, ACH/check processing, point-of-sale systems, encrypted hardware, customer communications, and customizable gift and loyalty programs.

Committed to enhancing operational efficiency and customer satisfaction, Dealer Pay's solutions are designed to integrate seamlessly with dealership management systems (DMS) and provide real-time reporting and analytics. Their PCI-DSS certified platform ensures secure transactions and compliance with industry standards. Dealer Pay's dedication to innovation and customer-centric service has earned them a reputation as a trusted partner in the automotive retail sector.

About this role

Dealer Pay is seeking a dynamic and driven Regional Sales Manager to grow our footprint and increase sales within a designated territory. This role is focused on building strong relationships with auto dealers, Automotive Trade Association Executives (ATAE) partners, and other key stakeholders. As a true hunter, you will be responsible for identifying new business opportunities, leading product demonstrations, and driving adoption of our innovative payment solutions. This position offers uncapped earning potential, including a competitive base salary, monthly software commissions, and residual commissions.

What You’ll Do:

• Meet or exceed assigned sales quotas and regional growth targets
• Champion and grow awareness of the Dealer Pay brand in your territory
• Prospect and connect with new dealerships and potential customers through cold outreach and follow-ups
• Build and nurture relationships with existing clients to encourage retention and upselling opportunities
• Representing Dealer Pay at industry trade shows and events to network, generate leads, and engage with current customers
• Deliver compelling demonstrations of Dealer Pay’s full suite of solutions to decision makers
• Strong verbal and written communication abilities for effective presentations and follow-ups.
• Ability to organize, prioritize, and execute tasks efficiently across multiple accounts and prospects.
• Ability to drive deals to completion, negotiating terms that balance customer satisfaction with company goals.
• Monitor market trends and competitive activity to identify new opportunities for growth
• Provide regular sales reports and updates to the leadership team
• Maintain accurate and up-to-date records in the CRM system

What You’ll Need:

• 5+ years of B2B sales experience, with a minimum of 3 years in SaaS, fintech, or technology sales.
• Demonstrated success in outbound prospecting, lead generation, and converting cold leads into active opportunities.
• Proven track record of building and managing a high-velocity sales pipeline in a self-sourced environment.
• Experience managing association or referral partners, and leveraging those relationships to drive revenue growth.
• Skilled at conducting outreach campaigns via phone, email, LinkedIn, and events — with persistence and creativity.
• Strong consultative selling skills, with experience presenting to stakeholders at all levels, including senior level executives.
• Proven ability to develop go-to-market strategies within a defined territory or vertical, especially where partnerships play a key role.
• Hands-on experience managing the full sales cycle — from discovery and demo through negotiation and close.
• Proficiency with CRM tools (e.g., Salesforce, HubSpot) and sales enablement platforms to track activity, pipeline health, and forecasting.
• Familiarity with co-selling motions, joint-marketing efforts, and collaborative partner sales strategies.
• Willingness to travel within the assigned region (up to 50%) for partner meetings, on-site demos, and industry events.
• Bachelor’s degree, preferred

Bonus Qualifications:

• Sales methodology training and/or certifications (SPIN, MEDDIC, Challenger, Sandler, Gap, etc)

• Experience selling software and/or financial services or payments solutions into the Dealership market

Note: This job description is intended to outline the general responsibilities and requirements of the role. It is not an exhaustive list of all duties, tasks, or responsibilities that may be required. Responsibilities and priorities may evolve over time, and the company reserves the right to make changes at any time with or without notice.

Vehlo is an equal opportunity employer that is committed to diversity and inclusion in the workplace. We prohibit discrimination and harassment of any kind based on race, color, sex, religion, sexual orientation, national origin, disability, genetic information, pregnancy, or any other protected characteristic as outlined by federal, state, or local laws.

This policy applies to all employment practices within our organization, including hiring, recruiting, promotion, termination, layoff, recall, leave of absence, compensation, benefits, training, and apprenticeship. Vehlo makes hiring decisions based solely on qualifications, merit, and business needs at the time.