Technical Project Manager

About the Role

Our model is prototype-first. Every engagement starts with a paid 2–6 week discovery project that gives clients something real: a working prototype on their actual workflows, not a slide deck of ideas. From there, we move into a full product build alongside the client's team, shipping production software they own and evolve themselves.

You'll be the operational spine of how we deliver. That means owning the path from "here's what we're building" to "it's live and the client's team is running it" – across AI agents, automation workflows, and custom internal tools. You're not just tracking tasks. You're making product decisions in the details: sequencing what ships, catching integration risks before they stall a build, and coaching clients through what it means to own a product they've never had before.

This role carries real technical and product judgment. You need to follow a data flow, have an opinion on how an agent should handle an edge case, and translate between a CFO describing a broken process and a developer asking what the schema should look like. If you've only ever coordinated, this isn't that.

What You'll Do

• Own delivery from prototype through production. Strategy defines what to build. You define how and when it gets built – breaking product roadmaps into sequenced releases, scoped to what can actually ship in each phase. When reality shifts, you replan and realign without waiting for someone to tell you to.
• Be in the product details. You're not handing specs over a wall. You're in the build, catching ambiguities in a workflow spec before a developer hits them, pressure-testing whether an AI agent's logic actually handles real-world inputs, and making scope calls when something has to give.
• Keep strategy, design, and development aligned. Lead standups, maintain delivery systems in Notion, and make sure everyone knows what's happening and what's next. Facilitate handoffs between strategy and build by identifying gaps early and resolving them before they stall delivery.
• Communicate progress and risks before they become surprises. Proactively surface what's on track, what's shifting, and what needs a decision to both internal teams and client stakeholders.
• Coach clients into product ownership. This is the part most PMs skip. You help clients understand what they're getting, how to think about their backlog, how to prioritize what comes next, and how to run the system after we step back. The goal isn't just adoption, it's ownership.
• Refine how we deliver. Build and improve the internal playbooks, templates, and delivery systems so the next project starts smarter than the last one.

What Success Looks Like

In your first 12 months:

• Developers say "that spec was spot on," not because you over-documented, but because you understood what they needed to move.
• Clients feel informed and in control throughout the build, not left guessing between check-ins.
• Release plans hold. When scope shifts, you replan quickly and teams aren't waiting for direction.
• AI agents and automations go live, work as intended, and clients want to keep building with us because the first thing we built together showed them what's possible.
• Clients can describe their own product roadmap and make prioritization decisions without us in the room.
• There's a clear delivery methodology that the whole team follows, not every PM running it their own way.

Who We're Looking For

• 5+ years managing technical implementations in consulting, agency, or product delivery environments. You've shipped custom software or internal tools (AI agents, automation platforms, or operations systems) not just rolled out SaaS.
• You think in releases, not tasks. You know how to break a product roadmap into phases, sequence builds against dependencies, and make scope calls when something has to give. A Kanban board is a tool, not the job.
• Technical systems thinking. You can follow a data flow, understand how an integration or AI agent works under the hood, and have a real conversation with a developer about what's feasible without writing the code yourself.
• Experience coaching non-technical clients through product thinking. You've helped a business stakeholder understand what a backlog is, how to prioritize it, and why they should care about it beyond go-live.
• Comfortable with AI and automation in practice. You've delivered projects involving AI agents, workflow automation (Zapier, Make, n8n, or similar), or custom automation, and you understand how they work, not just what they do at the surface.
• Strong client-facing instincts. You've managed expectations across business and technical stakeholders simultaneously. You know how to hold a timeline without burning a relationship.
• Bias for clarity over process. You've worked within Agile, Waterfall, and everything in between, and you know when to flex the framework to fit the engagement. You build systems other people actually use, not boards that only make sense to you.

Before You Apply

A few things worth knowing so we're both making a good call:

• Traditional enterprise or IT program management backgrounds (JIRA-heavy, change-control-board, 50-slide status decks) won't translate well. We work fast, with smaller companies, building real products.
• Pure coordination or scheduling roles are a different muscle. This role requires genuine technical fluency and product judgment, not just tracking tasks and running standups.
• If you need a fully defined scope before you can start moving, this will be uncomfortable. Requirements evolve, and you'll be expected to help shape them, not just execute against them.
• People who view delivery as separate from the product will find this frustrating. What ships is your responsibility. You're not just keeping trains on time, you're making sure they're going somewhere worth going.

What You'll Get

• Real ownership at a pivotal stage. You're joining as we build the systems to scale from 15 to 50+ people. How we deliver is still being shaped, and you'll shape it.
• Direct collaboration with the founders. No layers, no politics, no six-month wait to get a decision made.
• Remote-first. Anywhere in Canada with at least 3 hours of overlap with Pacific time.
• A team that builds real things. Strategists, designers, and developers who ship working products, not consultants producing deliverables for deliverables' sake.
• Competitive compensation, benefits, and real time off.

About Switchboard

Switchboard is a growing product studio for internal operations. We work with COOs, CFOs, and ops leaders at companies where the team has become the glue between disconnected systems, manual processes, and spreadsheets that everyone is eager to move on from. We build the custom software, AI-powered workflows, and automation that replaces the compromises they've learned to live with.

Every partnership starts by understanding how work really moves through an organization, then building the tools that match that reality. We're a small product-minded firm that takes the work seriously without taking ourselves too seriously. The challenges are real, and the things we build actually make people's jobs better.