Founding Sales Development Representative (SDR)

The company is looking for a Founding Sales Development Representative (SDR) to join our fast-growing Sales team. This is not a typical SDR role; it’s a ground-floor opportunity to build our outbound engine from scratch and fast-track into an Account Executive role within 6–9 months for the right performer.

Your mandate is to generate pipeline, qualify opportunities, and open doors across US school districts. You’ll operate as the tip of the spear, creating opportunities that accelerate the company’s growth in key markets.

This role is perfect for someone who is hungry, entrepreneurial, and wants to prove themselves quickly and move up fast. You’ll work directly with Sales leadership and gain visibility across the entire company.

This is a remote role and may include occasional travel.

Why the company?

The company is a leading North American tech company that provides all-in-one transportation management software to K-12 school districts. Across our customer base, we enable hundreds of transportation directors to save thousands of dollars every year by running all facets of their operations entirely through our intuitive, and easy-to-use platform.

The company’s product suite is embedded across the majority of school districts in Canada and is currently making significant inroads in the US market, having won contracts with some of the largest school districts in the country including Miami-Dade (Florida), Prince George's (Maryland), Guilford (North Carolina), as well as many others. The company has a history of serving the education market and is favorably positioned to further penetrate the US market in the coming years.

The company’s leadership team consists of seasoned entrepreneurs who have significant experience in building and growing multiple successful software businesses including: (i) FieldEdge , a leading provider of software for the field services market which the team grew more than 5x and sold to a mega-cap private equity fund, and (ii) AutoLeap , a leader in the auto repair software market that has raised more than $50 million from some of the most reputable VC firms in Silicon Valley .

Requirements

As a successful Founding SDR, you will

• Own top-of-funnel pipeline generation through cold calling, emailing, LinkedIn outreach, and creative outbound tactics.

• Qualify inbound and outbound opportunities and partner closely with Account Executives for smooth handoffs.

• Run targeted outbound campaigns to penetrate high-value school districts across the U.S.

• Experiment aggressively to refine messaging, test sequence strategies, and improve conversion.

• Collaborate with Sales leadership on outbound approach, territory strategy, and account prioritization.

• Help shape our sales systems , including CRM structure, Outreach sequences, enrichment workflows, and reporting.

• Represent the company at conferences to support onsite prospecting and pipeline creation.

• Advance quickly: strong performers have a defined 6–9 month path to an AE role, with mentorship and support to get there.

To be successful in this role, you will need

• Extreme drive and grit: You love outbound, you love the hunt, and you love creating opportunity.

• Entrepreneurial mindset: Comfort in an environment where there isn’t a playbook yet (you’re helping build it).

• Strong communication & questioning skills: You can capture attention and uncover pain quickly.

• High organization & tech-savviness: Proficiency with CRM and sales automation tools.

• Curiosity: You dig deep, ask smart questions, and constantly refine your approach.

• Coachability: You’re hungry for feedback and improve fast.

• Resilience: You handle rejection well and maintain high energy.