Permanent Remote Call Monitoring Jobs in Whitby, ON

Director of Product, AI

Toolbx  ·  Product  ·  Full-time  ·  Remote (USA or Canada)  ·  Reports to VP

About Toolbx

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.

Our platform is growing fast. 130+ dealers are live across USA and Canada. 1000s of daily transactions are flowing through our platform. The next chapter is about depth, smarter integrations, AI-driven ordering intelligence, and a product surface that earns contractor loyalty at scale.

The Role

We’re looking for a Director of Product who leads from the front. You’ll own the roadmap, the execution, and the outcomes. You’ll also be the person running discovery calls with dealers, prototyping solutions, and going deep on a thorny integration problem when the situation calls for it. 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. This is a player-coach role with a builder’s mindset. We have no need for a professional manager.

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. You’ll be measured on product velocity and outcomes, not headcount.

What You’ll Own

Product roadmap & platform strategy

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.

Hands-on execution

Lead discovery, prototype solutions, and ship features from concept to launch. You’re not above digging into an edge case in a supported ERP or jumping on a call with a dealer’s IT team. 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.

Integration & ecosystem depth

You’ll own the platform to ERP integration strategy across our dealer ecosystem. Epicor BisTrack, Epicor Eagle, ECI Spruce, DMSI Agility are core supported ERPs. Knowing where to build, where to partner, and where to hold the line is a required skill here.

Team leadership

Manage and develop a team of 2-3 PMs, from near-peer senior level Group Product Managers to early career Associate Product Managers. Give them clarity, remove blockers, and create the conditions for excellent work. Hire well. Coach constantly. Raise the bar on craft without creating bureaucracy.

Cross-functional alignment

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

Design and maintain the operating system for how product work gets done. 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.

What We’re Looking For

• 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
• A track record of owning outcomes, not just outputs. You can point to metrics that moved because of decisions you made
• 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.
• Integration fluency, you’ve navigated ERP, payments, or similarly complex third-party ecosystems and know how to scope without blowing up delivery
• Strong discovery instincts, you talk to customers regularly and your roadmap shows it
• Exceptional written communicator, your specs are clear, your reasoning is traceable, and your executive updates don’t require a decoder ring
• Bias for action; discomfort with ambiguity is disqualifying. You make calls with imperfect information and own the results
• Systems thinker you see a product org as a set of workflows to be designed and optimized, not just a team to be managed. You look at how product and engineering collaborate and ask “what can I automate, accelerate, or eliminate?”
• Flexibility to travel regularly to interface with our customers at their locations

Nice to Have

• LBM or distribution familiarity, the industry has its own language. You’ll learn it either way, but fluency is a head start
• 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.

About Us

Toolbx is a fully remote team building an AI-native platform for an industry most SaaS companies have ignored. We move fast and we’re deliberate about it, documentation matters, async is default, and we hire people who can own things without waiting to be told. If you want to build the product operating system for the next generation of LBM technology, we’d like to talk.