Director of Product, AI Toolbx · Product · Full-time · Remote (USA or Canada) · Reports to VP Toolbx is a vertical software platform for the lumber and building materials industry, offering dealers and distributors a suite of tools, from AR and payments to eCommerce and AI-powered ordering. We connect dealers, contractors and suppliers through a commerce layer that actually understands how the industry works, job-site deliveries, trade accounts, ERP-native pricing, mobile-first ordering. The industry is mid-transformation, and we’re the team building the rails it runs on.

The next chapter is about depth, smarter integrations, AI-driven ordering intelligence, and a product surface that earns contractor loyalty at scale. We’re looking for a Director of Product who leads from the front. But you won’t do it all manually, you’ll design the system that gets it done, using AI agents and automation alongside your team to maximize output.

You’ll report directly to the VP, Strategy & Partnerships and manage a small product team, working alongside a tight-knit cross-functional group spanning engineering, customer success, design, and commercial. Define and drive the roadmap across Toolbx’s core platform, ordering, payments, catalog, integrations, and AI capabilities. Translate market signals, dealer feedback, and internal data into a sequenced plan that balances near-term wins with durable platform value.

Lead discovery, prototype solutions, and ship features from concept to launch. You also know which parts of the product development cycle can be automated and you build those systems.



Your team looks to you to model what great product work looks like in an AI-native company.

Travelling to meet customers face to face is expected. AI product development Own the product surface for Toolbx’s AI-powered ordering automation (AIOA). This is live, it’s differentiating, and it needs a product leader who can take it from early-stage to a core reason dealers choose Toolbx over anyone else.

Manage and develop a team of 2-3 PMs, from near-peer senior level Group Product Managers to early career Associate Product Managers. Partner closely with Engineering, Customer Success, Sales, and Design to drive execution. Be the person who keeps commercial, technical, and customer perspectives in the same room — and makes a decision when they’re in tension.

Product operations & AI workflows Build agent-assisted workflows for feature request triage, competitive monitoring, status reporting, and roadmap communication. Accelerate engineering development cycles by automating handoffs, specs, and coordination between product and engineering. Your goal is to run a product function that punches far above its headcount by combining human judgment with AI-driven execution. 8+ years in product management,



with meaningful time in complex B2B SaaS or vertical software platforms ~3+ years managing PMs, you’ve grown people, not just shipped features ~ Hands-on with AI product development, you know what’s real, what’s hype, and how to ship AI features that earn user trust over time ~ Experience building AI-assisted workflows for your own team’s operations not just shipping AI features for customers.

You’ve used agents, automation, or AI tooling to multiply your team’s output and accelerate product-to-engineering handoffs. ~ Robust discovery instincts, you talk to customers regularly and your roadmap shows it ~ Flexibility to travel regularly to interface with our customers at their locations LBM or distribution familiarity, the industry has its own language. Mobile-first product experience, a large share of our customer’s customers are ordering from job sites, not desks Vertical SaaS or industry cloud background, you’ve built for a buyer who lived in spreadsheets and phone calls before using your product Early-stage product leadership, you know how to build process that helps without slowing things down Experience at a company undergoing AI transformation you’ve navigated the shift from traditional to AI-native product development and can bring that playbook to accelerate our engineering and product velocity. Toolbx is a fully remote team building an AI-native platform for an industry most SaaS companies have ignored.

If you want to build the product operating system for the next generation of LBM technology, we’d like to talk. #

📌 Director of Product, AI (Remote Canada or US) (Winnipeg)
🏢 TOOLBX
📍 Winnipeg