Company Overview

Our client is a B2B SaaS company (~45 people) helping Microsoft 365 customers manage, secure, and govern their content for enterprise AI readiness. Their core thesis: as Microsoft adds more capabilities, it becomes harder for admins to manage their environments and harder for end users to know what to use. They sit in that gap, and have been proven right over time as M365 has expanded.

The AI angle is central to their current positioning: most organizations trying to deploy enterprise AI point it at their corporate content and get poor results, not because of the models, but because the underlying content is outdated, redundant, and ungoverned.

Why This Opportunity Is Compelling

They describe their market position as “dolphins in the wake of Microsoft’s cruise ship”: they must constantly innovate ahead of Microsoft to capture the gaps in their product, without drifting so far out that they lose the momentum of that wake. It is a high-stakes, high-creativity product environment where the right leader will have genuine impact. This is a ground-up build. The incoming Director of Product will have the mandate to reimagine how the company does product: how they engage with customers, how they validate ideas, how they prioritize across customers, Microsoft’s roadmap, and partner needs. The CEO’s personal passion is product, which means this person will have a genuine thought partner at the top of the company and real visibility from day one. For a product leader who loves the building phase, this is the role.

The Role

The incoming Director of Product will step into a player-coach IC role initially, working alongside the CEO while rebuilding the team over time. This person will set the standard, mentor the existing PM, and grow the function as the company scales.

The CEO has described the current state of product as running on instinct. The mandate for this hire is to operationalize that instinct: take the knowledge and intuition that exists in the business and turn it into a repeatable, scalable product process.

Responsibilities

• Own the product vision and roadmap, bringing a clear point of view and backing it with data
• Establish and enforce product processes (We use a Shape Up/Agile hybrid); evangelize the methodology across the team
• Act as the primary customer-facing product voice: call customers, validate ideas, and champion the feedback loop
• Mentor and develop the existing technical PM; hire and build out the product team over time
• Partner closely with the CEO and CTO as a genuine thought partner, pushing back where warranted
• Navigate the three-way prioritization challenge: customer needs, Microsoft’s evolving roadmap, and partner requirements
• Lead AI capability development within the product, identifying where AI can be leveraged effectively across the business
• Build POCs and experiment with AI tooling (e.g., Claude Code) as part of the product development process
• Drive improvement by iteration, not perfection: bias toward action and learning fast

Must-Haves

• Strong B2B SaaS product background with experience scaling a company
• Player-coach mentality: comfortable doing IC work while also leading and mentoring
• Driven to action; iterates fast rather than planning indefinitely
• Owns and evangelizes process, not just follows it
• Passionate, hands-on AI adopter: actively experimenting with AI tools, not watching from the sidelines
• Customer-facing confidence: able to call customers, validate ideas, and act as a product evangelist
• Strong presence in the room: able to hold their own in debate with a CEO whose passion is product, and back up their point of view with data
• Remote work experience
• Based in Canada

Nice-to-Haves

• Microsoft 365 / M365 ecosystem familiarity
• Experience with Shape Up methodology
• Prior experience in a founding or early-stage PM role