Sr Product Manager

Role: Sr Product Manager

Location: Downtown Toronto (hybrid) 

Compensation: 140-160 CAD + equity

About Us:

We exist to modernize the way that vendors and property managers work together. We do this by building a complete vendor lifecycle management solution, purpose-built for the world of commercial real estate. Today, over 10,000 buildings and 70,000 vendors rely on VendorPM for credentialing, tendering, and contract management. We drive serious efficiency and cost savings for property managers, while unlocking growth opportunities for vendors across North America.

We’re one of Toronto’s fastest-growing startups, a certified “Great Place to Work,” and recognized in 2023, 2024 and 2025 as one of the Best Workplaces in Canada. Backed by world-class SaaS and PropTech —investors-Bessemer Venture Partners, the former CEO of Twitter, Prudence VC, and Navitas Capital-we’re just getting started.

Our team is scrappy, resourceful, and laser-focused on impact. If you’re someone who thrives in fast-moving environments, loves turning ideas into action, and wants to grow alongside the business you’re helping build-we want to hear from you.

The Role

The Senior Product Manager will report directly to the Co-Founder & COO and own product execution across VendorPM's core platform and AI-powered vendor solutions. You'll work at the intersection of complex business problems and technical systems - bringing structure to ambiguity, turning strategic priorities into executable plans, and staying close to the work as features move from discovery to launch.

We've built a platform that 10,000+ buildings and 70,000 vendors rely on daily - and moved fast to get here. Now we need a product operator who can build the discipline and depth to support what comes next: larger customers, more complex requirements, and a product vision centred on agentic procurement.

You'll join a company with strong engineering and product leadership already in place, and founders who are deeply involved in the business. What we need is a PM who can match that clarity on the product side - someone who can work fluidly across technical and commercial contexts, hold a high bar for what ships, and make good decisions with incomplete information.

What You'll Work On

The core challenge is defining and shipping enterprise-grade software with real business complexity - systems that handle the full vendor lifecycle, from compliance and credentialing through tendering, procurement, and contract management. The business logic is deep, the customer environments are varied, and the organizations that depend on this platform have high expectations.

Underneath that is a longer arc: everything you shape is rowing toward a platform where AI handles routine vendor management end-to-end, with property managers focused on relationships and exceptions. That vision shapes the product decisions you'll make today - how features are scoped, how AI capabilities are evaluated, and how the roadmap is prioritized to build toward something genuinely transformative.

You'll also help establish how data flows through the platform - building reporting infrastructure, enabling self-serve analytics for internal teams, and ensuring data quality supports both product decisions and customer-facing features.

What You'll Do

Product Strategy & Roadmap

• Own product areas spanning vendor data infrastructure, AI-powered features, and compliance management systems

• Translate business objectives into technical roadmaps with clear dependencies and milestones

• Define requirements that account for integration constraints, data dependencies, and architectural tradeoffs - in close partnership with engineering

Execution & Delivery

• Drive features from discovery through launch, scoping work accurately and identifying risks early

• Own cross-functional coordination across engineering, design, data, and GTM for your product areas

• Build and maintain evaluation frameworks for AI features - defining what "good" looks like and how we measure it

• Create visibility into progress through clear documentation, roadmap management, and crisp stakeholder communication

AI-Forward Product Process

• Evolve how the team builds products using AI tools - from discovery and documentation to prototyping and validation

• Stay current on emerging AI tooling and bring relevant innovations back to the team

• Define when AI-assisted approaches add genuine value versus when they don't

What We Value

High Standards: Your PRDs are tight, your tickets are unambiguous, and your stakeholder updates are crisp. The quality of what your team ships reflects the bar you hold yourself to.

Intellectual Curiosity:  You ask questions until you understand how systems actually work - not just what they're supposed to do. You're solution-focused and energized by making complex things simple.

Full Ownership:  Problems are yours to solve. You don't wait for permission, and when you learn new information, you course correct fast.

What we are looking for

• 5+ years in product management, with experience owning technically complex products

• Comfort working directly alongside engineers - you understand technical constraints, ask good questions, and don't need things translated down to you

• Track record of shipping data-intensive or AI-powered products, with experience defining success metrics and evaluation approaches

• Proficiency with project management tools (Jira, Linear, or similar) - you know how to create visibility and drive execution

• Comfort with data and analytics tools - you can build a dashboard, interpret query results, and answer your own questions without always needing a data team

• Active experimentation with AI tools in your daily workflow - you understand their capabilities and limitations firsthand

• Strong documentation discipline - PRDs, specs, and process documentation that teams actually use

• Strong systems thinking - you naturally see dependencies, feedback loops, and second-order effects

• Comfort with ambiguity and rapid iteration - you make decisions with incomplete information and adjust as you learn

What’s In It For You

• Meaningful equity in what you help build

• Comprehensive health, dental, vision, and life insurance

• 3 weeks vacation + 8 wellness days

• Employer top-up for maternity and parental leave

• Downtown Toronto office with hybrid flexibility (2 days) 

• Regular team events and a close-knit culture

• A chance to grow with a fast-moving company where your work has direct impact on an industry

Bonus if you have

• Experience in PropTech, real estate, construction, or B2B marketplaces

• Background in vendor management, compliance systems, or multi-sided platforms

• Familiarity with LLM-based products, RAG systems, or context engineering

• Experience driving AI evaluations in partnership with data and engineering teams

• Hands-on experience with rapid prototyping tools (Lovable, v0, Bolt) for validation

• Experience with enterprise sales cycles and complex customer environments

• Startup experience, particularly in companies navigating growth and scale

Interview Process

• Step 1: Google Meet exploratory call with HR
• Step 2: 1st Interview with Co-Founder & COO
• Step 3: 2nd Interview with fractional CPO 
• Step 4: Focused take-home exercise (~3 hours) - a realistic product problem that reflects the work you'd be doing here
• Step 5: In-person task review and discussion - COO, FCPO

Notes:

1. This posting is for a current opening

2. We are committed to providing an inclusive, accessible environment where all employees and clients feel valued, respected and supported. We aim to build a workforce that reflects the diversity of our communities, and to create an environment where every employee has the opportunity to reach their potential.