GM, AI Products

Datatrac is a leading last-mile and courier management platform serving operators across North America. We are now at an inflection point: AI will fundamentally redefine how orders are captured, dispatched, and managed across our customer base. We are looking for a builder to lead that transformation. 

This is not a caretaker role. This is a zero-to-one and one-to-scale mandate. 

The Role 

We are hiring a GM, AI Products to lead the end-to-end vision, execution, and commercialization of Datatrac’s AI product portfolio. You will report directly to the CEO of Datatrac and be responsible for redefining our product offerings through AI. 

Datatrac already has early-stage AI-enabled phone and email order creation tools in market. They work. They are validated. Now they need to be transformed from proof-of-concept into a scaled, revenue-driving product line that reshapes how courier businesses operate. 

You will own that outcome. 

This role is based in Toronto and requires significant travel to customer sites across the U.S. and Canada to deeply understand workflows, refine product-market fit, and accelerate adoption. 

What You’ll Do 

Redefine the Product Strategy 

• Set and execute the AI product vision for Datatrac. 

• Expand AI-enabled order capture (email and phone agents) into a scalable, high-impact product line. 

• Identify new AI-driven opportunities across dispatch, operations, customer service, and workflow automation. 

• Translate customer pain points into technical product direction. 

Drive Go-To-Market 

• Build the commercialization strategy for AI offerings. 

• Partner with sales to position and sell AI solutions into the existing customer base and new logos. 

• Own pricing, packaging, messaging, and competitive positioning. 

• Be customer-facing and hands-on in early deals. 

Build Strategic Partnerships 

• Identify and execute partnerships across AI infrastructure, telephony, integrations, and ecosystem players. 

• Leverage external capabilities to accelerate time to market. 

Work Deeply with Engineering 

• Collaborate closely with dedicated AI engineers within Datatrac. 

• Translate business objectives into clear technical roadmaps. 

• Prioritize ruthlessly and ship quickly. 

• Use real-world deployment feedback to continuously improve the product. 

Operate as a Builder 

• Wear multiple hats: product leader, operator, GTM driver, strategist. 

• Travel on-site to customers to observe workflows and accelerate adoption. 

• Move fast, test fast, iterate fast. 

What We’re Looking For 

This is a high-agency role. We are not looking for a corporate manager. 

You must have: 

• A strong hands-on technical background (engineering or equivalent deep technical experience). 

• Demonstrated ability to ship AI-enabled products. 

• Commercial instincts and real business acumen. 

• Experience taking products from early-stage to scaled revenue. 

• Comfort working directly with customers and sales teams. 

• Exceptional communication and teamwork skills. 

• Hustle, grit, and ownership mentality. 

You should be equally comfortable: 

• Reviewing system architecture, 

• Pitching a strategic customer, 

• Designing a pricing model, 

• And spending two days onsite understanding a courier’s operational bottlenecks.