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Calyptus
VP EngineeringCalyptus • Winnipeg, Canada
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VP Engineering

VP Engineering

Calyptus • Winnipeg, Canada
4 days ago
Job type
  • Full-time
Job description
Overview 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 COO and own technical architecture, engineering culture, and delivery execution.

We've moved fast and hit our growth stride with signed enterprise customers, and built a platform that 10,000+ buildings and 70,000 vendors depend on daily. That speed created a strong foundation—and also the kind of technical and process debt you'd expect from a company that prioritized shipping over polish.

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.

We expect you to be hands‑on with AI tooling. If you’re not already using Cursor, Claude, or similar tools to accelerate your own work and thinking about how AI changes engineering team productivity, this isn’t the right fit.

What we are looking for

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

What you’ll be doing Technical Leadership

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—and build team judgment for making these calls well

Lead a team of ~10 engineers and set the bar for what great engineering looks like at VendorPM—we believe strong engineering culture is built through in‑person collaboration, whiteboarding sessions, and solving hard problems together

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

AI‑Forward Development & QA Practice

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

Delivery & Execution

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

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VP Engineering • Winnipeg, Canada

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