Head of Sales

Position: Head of Sales

Location: Toronto, ON

Employment Type: Full-Time

Industry: Fleet Management / Telematics / SaaS / Transportation Technology

Pay: 130k

Position Overview:

Our client is a growing technology company specializing in connected vehicle and fleet telematics solutions that help businesses improve fleet safety, operational efficiency, productivity, and overall fleet costs. Its technology combines real-time vehicle data, GPS tracking, driver behavior analytics, fuel and mileage management, fleet administration, and field-operations insights to help organizations make smarter, data-driven decisions. With an expanding presence across North America, the company is seeking a hands-on Head of Sales to lead sales growth and accelerate enterprise adoption. This is a true player-coach/start-up leadership role, requiring someone who is comfortable with prospecting, networking, client meetings, presentations, negotiations, closing deals, and building sales processes from the ground up. The ideal candidate will have deep experience selling into fleet management, transportation, logistics, automotive, mobility, telematics, or related technology markets, along with an established and active network of industry contacts and a proven track record of enterprise sales.

What will you be doing?

• Develop and execute the company's enterprise sales strategy across North America.
• Personally identify, prospect, develop, and close enterprise fleet-management opportunities.
• Leverage an established network of industry contacts to generate new business.
• Build relationships with senior decision-makers, including Fleet Directors, VP Operations, Transportation Leaders, Procurement, CFOs, and C-suite executives.
• Own the entire enterprise sales cycle from prospecting and discovery through negotiation, closing, and handoff.
• Develop strategic partnerships and channel relationships within the fleet, transportation, automotive, and technology ecosystem.
• Identify new markets, industries, and enterprise accounts with strong growth potential.
• Conduct product demonstrations and present compelling business cases focused on ROI, efficiency, safety, and cost reduction.
• Develop proposals, pricing strategies, sales presentations, and commercial agreements.
• Build and maintain a strong sales pipeline and accurately forecast revenue.
• Work closely with product, implementation, and customer success teams to ensure a strong customer experience.
• Establish sales processes, CRM discipline, reporting, KPIs, and scalable sales practices.
• Represent the company at industry events, conferences, trade shows, and customer meetings.
• Recruit, mentor, and eventually build out a high-performing sales team as the business scales.
• Bring market intelligence and customer feedback directly to the leadership and product teams.
• Be willing to roll up your sleeves and personally do what is required to win business in a fast-moving start-up environment.

What We're Looking For

• 8+ years of progressive B2B/enterprise sales experience, preferably within fleet management, telematics, transportation technology, SaaS, automotive technology, logistics, or a related industry.
• Demonstrated success selling enterprise solutions to large organizations.
• An active and relevant network of contacts within the fleet/transportation ecosystem.
• Existing relationships with fleet operators, transportation companies, logistics organizations, leasing companies, or other large commercial fleet customers.
• Proven track record of generating new business and consistently closing complex enterprise deals.
• Strong understanding of fleet management, telematics, connected vehicles, IoT, SaaS, or fleet technology solutions.
• Experience selling to C-level and senior operational decision-makers.
• Strong business development, networking, negotiation, presentation, and closing skills.
• Entrepreneurial mindset with the ability to operate independently and create opportunities rather than wait for leads.
• Highly hands-on, commercially driven, and willing to be involved in both strategy and execution.
• Strong communication and relationship-building skills.
• Willingness to travel for customer meetings, conferences, and industry events as required.