Founding Account Executive

We are seeking a Founding Account Executive to join a fast-growing startup focused on providing innovative solutions in the telematics and commercial trucking sector. In this role, you will be responsible for driving $1M in annual revenue, managing the entire sales cycle from prospecting to closing. You will engage with clients across various industries, including insurance, software, financial services, and logistics, handling deal sizes ranging from $25k to $250k. Building strong relationships with executives and technical leaders will be essential, as will providing insights and feedback to refine sales strategies and improve product offerings. Candidates should have a minimum of 6 years of account executive experience, with at least 3 years in enterprise sales. A proven track record in managing complex sales processes and a strong understanding of technical products are critical. Excellent communication skills and a proactive approach to identifying risks and opportunities within your sales pipeline are necessary. Preferred qualifications include experience in early-stage startups, a technical degree, and prior sales experience in the insurance or financial sectors. Compensation for this role includes a base salary with variable earnings, totaling between CA$180,000 and CA$200,000, along with a comprehensive benefits package including health/dental coverage, paid time off, and professional development support. Candidates must be located in Toronto and able to commute to the office regularly.