Enterprise Sales Executive

Company Overview:

Lightspeed is a leading provider of cloud-based software for dealerships and Original Equipment Manufacturers (OEMs), serving the Powersport, Marine, RV, Trailer, Outdoor Power Equipment, and Golf Cart industries. Lightspeed’s Dealer Management Solution (DMS) enables dealerships to optimize their end-to-end business operations, including sales, parts, service, rentals, accounting, and Customer Relationship Management (CRM). When implemented into their daily operations, Lightspeed helps dealers increase their profitability by selling more units, service, and parts, all while creating a more streamlined experience for customers. For nearly 40 years, Lightspeed has been empowering 4,500+ dealers across North America with the tools and technology they need to manage their dealerships.

The Enterprise Sales Executive is a strategic, high-impact role responsible for acquiring and expanding business within the largest and most complex dealership groups across the RV, Marine, Powersports, Trailer, and Golf verticals. This position requires a seasoned enterprise seller who can navigate multi-location organizations, engage executive-level stakeholders, build consensus across departments, and architect long-term technology transformation plans.

You will manage the entire enterprise sales cycle—from prospecting and discovery through evaluation, financial modeling, contracting, and executive alignment. You will use a combination of outbound prospecting, industry networking, partnerships, trade shows, and executive-level engagement to generate and close new enterprise business. This role requires strong business acumen, exceptional communication skills, and a proven ability to drive large scale deals to completion.

What you’ll do:

• Develop, manage, and execute strategic account plans for large, multi-rooftop dealership groups across RV, Marine, Powersports, Trailer, and Golf.
• Conduct deep discovery and map business processes to identify operational inefficiencies, revenue opportunities, and long-term strategic gaps Lightspeed can solve.
• Build executive-level relationships with Dealer Principals, CFOs, COOs, Controllers, and General Managers.
• Lead complex sales cycles, including scoping, ROI analysis, custom contracting, risk management, and executive-level presentations.
• Manage outbound prospecting and pipeline generation efforts to create new enterprise opportunities.
• Partner closely with Solutions Engineering, Implementation, Product, Finance, and Executive Leadership to deliver a cohesive and successful sales motion.
• Represent Lightspeed at industry events, trade shows, and association gatherings to build market visibility and drive new enterprise engagement.
• Maintain expert-level knowledge of Lightspeed’s products, competitive landscape, market trends, and dealership operational workflows.
• Accurately manage pipeline, forecasting, and CRM documentation.
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What you should have:

Qualifications:

• Minimum 3 years of proven enterprise sales experience, ideally selling SaaS, ERP, DMS, or other complex technology solutions.
• Demonstrated success managing long, multi-stakeholder, and multi-location enterprise sales cycles with quota attainment or overachievement.
• An understanding one or more of the following industries: RV, Marine, Powersports, Trailer, or Golf (highly preferred).
• Ability to articulate ROI, operational impact, and financial modeling to executive teams.
• Experience building and presenting custom enterprise proposals to C-suite audiences.
• High level of business acumen, strategic thinking, and consultative selling skills.
• Self-motivated and comfortable owning a large, complex pipeline with long sales cycles.
• Excellent verbal and written communication abilities.
• Proficiency in CRM platforms (Salesforce preferred) and Windows-based applications (Word, Excel, Outlook).
• Willingness to travel for enterprise on-sites, trade shows, and executive meetings.

Inclusion and Diversity at Lightspeed:

At Lightspeed, we celebrate the uniqueness of every individual and encourage diverse perspectives. We believe that inclusion drives innovation and fosters meaningful connections. We are committed to building an environment where everyone feels valued and empowered to make an impact.

Equal Employment Opportunity Statement:

Lightspeed is an Equal Opportunity Employer and is dedicated to building a diverse and inclusive workforce. All qualified applicants will be considered for employment without regard to race, color, creed, ancestry, national origin, gender, sexual orientation, gender identity, gender expression, marital status, religion, age, disability, veteran status, or any other protected category.

Important Note:

Applicants must be authorized to work in the U.S.

Ready to apply?

Take the next step in your career—apply today and join a team where your skills will make an impact!