Vice President of Engineering

VendorPM

2d•Hybrid

About The Position

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 Vice President of Engineering will partner with the founders and product leadership to build the engineering organization that takes VendorPM to its next stage of growth. You'll report directly to the Co-Founder & COO and own technical architecture, engineering culture, and delivery execution. We've built a platform that 10,000+ buildings and 70,000 vendors depend on daily - and moved fast to get here. Now we need a leader who can build the maturity and discipline to support what comes next: larger customers, more complex requirements, and a product vision centred on agentic procurement. You'll set technical standards, make architectural decisions and shape the path toward AI systems that handle routine vendor management end-to-end. Critically, you'll build an engineering team where AI-native development is the baseline, not just a competitive advantage. Every engineer on this team is expected to use AI tooling as a core part of how they work, and you'll be the one who sets that standard and holds it. You'll join a company with strong product leadership, a clear strategic direction, and founders who are deeply involved in the business. What we need is an engineering leader who can match that clarity on the technical side - someone who can build a culture of ownership, quality, and velocity that scales with us.

Requirements

Deep experience (10-15 years) building or significantly improving an engineering organization - you've shaped culture and process, not just inherited a working machine
Deep technical fluency with modern web architectures - you've built and scaled systems on AWS/GCP with Node.js/TypeScript, GraphQL, React, and PostgreSQL
Track record of improving engineering delivery predictability and quality while maintaining team morale and velocity
Hands-on leadership style - you stay close to the code and can contribute technically when needed
Experience integrating AI/ML capabilities into production systems
Comfort with ambiguity and competing priorities: you've worked in startups or growth-stage companies where judgment matters more than playbooks
Strong opinions on engineering culture and process, informed by experience with what actually works

Nice To Haves

Experience in PropTech, real estate, or B2B marketplaces
Background with compliance systems, credentialing, or multi-sided platforms
Hands-on experience with LLM-based features, RAG systems, or AI agents in production
Experience building hybrid TypeScript/Python architectures for AI-intensive applications
Experience preparing engineering organizations for significant scale or exit

Responsibilities

Own architectural decisions across our platform - you'll need to understand our NestJS/PostgreSQL/Apollo GraphQL/React stack deeply enough to guide its evolution and make build-vs-buy decisions
Drive the technical strategy for AI integration, including evaluating when to extend our TypeScript stack versus introducing Python or other languages better suited for AI/ML and data-intensive workloads
Make nuanced tradeoffs between paying down technical debt and shipping features
Lead a team of ~10 engineers and set the bar for what great engineering looks like at VendorPM
Shift team structure and processes toward true full-stack ownership, moving away from rigid frontend/backend distinctions that create handoff friction and limit engineer growth
Build processes that create accountability and visibility without bureaucracy - sprint planning, estimation, and delivery tracking that enable engineers to own outcomes, not just tasks
Establish practices for AI-assisted development across the engineering team - we expect engineers to leverage tools like Cursor, Claude, and Copilot to accelerate their work
Build QA and testing approaches that account for AI-generated code: review practices, test coverage expectations, and quality gates that maintain standards while capturing productivity gains
Evaluate and integrate AI tooling into CI/CD, code review, and documentation workflows where it adds genuine value
Own engineering delivery against product roadmap commitments with realistic estimation and clear communication when plans change
Partner with Product on technical discovery to identify architectural prerequisites and risks before work enters sprints
Build the muscle for shipping reliably - we want a team that hits its commitments and knows how to scope appropriately