Head of Strategy

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.

The Role Our model is prototype-first. Instead of long strategy engagements that produce abstract decks, we lead with a paid 2–6 week prototype that gives clients something real. Strategy runs through every phase, it just happens through the lens of building, not talking about it. We think in products, not PowerPoints.

You’ll own the strategy function. That means building the team, the methodology, and the client relationships that let us deliver sharp, buildable strategy without a founder in every room. You start as a player‑coach, hands‑on with clients while setting the standard for your team. Over time, you shift into pure leadership as the person our clients trust to figure out what to build and why, and the person our delivery team relies on to translate business problems into product decisions.

What You’ll Do

Build and lead the strategy function.

Set the standard for how discovery, analysis, and product scoping get done at Switchboard. Create the playbooks, templates, and frameworks that make quality consistent and not dependent on any single person. Give direct, honest feedback. Build people who can eventually own client relationships independently.

Handle key client relationships.

You may not be on every project, but you're the person our team calls on when client priorities shift or when they need someone to tell them what's realistic.

Be the bridge between business problems and product decisions.

Sit with a CFO and understand why their reporting process is broken. Then sit with a developer and explain what needs to exist and how data should flow. You think in PRDs and product roadmaps, not BRDs and slide decks.

Stay embedded in delivery.

Strategy doesn't sit in a silo. You and your team work directly alongside TPMs, designers, developers, and BAs. What gets scoped is what gets built by the people next to you. No handoff to a different team.

Spot patterns and push our thinking.

You're across enough client work to see what's repeating, what's changing, and what's possible as AI tools shift how fast we can build.

What Success Looks Like In your first 12 months:

Clients trust you to guide product decisions without a founder in the room.

Prototype projects consistently convert to full engagements because scoping is sharp and clients saw something real.

Strategy deliverables are things designers and developers can build from directly. No weeks of re-discovery.

There's a documented methodology for how we run discovery, scope prototypes, and define product requirements.

You’ve taken over primary ownership of 2–3 major client relationships that previously required a founder.

Your team feels challenged, supported, and clear on how they grow.

Who We’re Looking For

7+ years in consulting, agency, or product strategy

serving mid‑market or SMB clients. You've led discovery, shaped product direction, and stayed close enough to delivery to know whether your recommendations actually worked. You've seen strategy disconnected from building, and you hated it.

You think in products, not PowerPoints.

When a client describes a problem, your instinct is what we'd build, not what we'd recommend in a deck. You've shaped real software products or custom internal tools.

Strong understanding of business operations.

You can walk into a company you've never seen, talk to people across departments, and quickly map how the business runs, where it breaks, and what matters most.

Technically fluent.

You don’t have to be a developer, but you understand relational data, APIs, and system integrations well enough to have real opinions. When a developer pushes back on a team's spec, you can help them have a productive conversation about it.

Experienced with AI and automation in practice.

You've used AI tools in real workflows, not just read about them. You know when automation helps and when it's noise.

Player‑coach wired.

You've managed a small team while not getting so far removed from the work that you don’t work with a client or two yourself. You've used this balance of experience to build internal playbooks or processes that outlasted your direct involvement.

You can run a room.

Equally comfortable with frontline staff and a CEO asking hard questions about ROI. Clients want you there when decisions get made.

Bias for action over perfection.

You’d rather build something rough and iterate than spend three months on a comprehensive strategy document.

Before You Apply A few things worth knowing so we’re both making a good call:

Enterprise transformation backgrounds

with purely cloud migrations or 50‑slide decks being your team’s main deliverable won’t translate well. We work fast, with smaller companies, building real products and utilities.

Pure software product management

is a different muscle. This role needs deep business consulting chops that inform, product thinking.

Document‑first thinkers

will find this uncomfortable. Our strategy work produces prototypes and product requirements, not reports that sit in a shared drive.

People who want to stay individual contributors

should know this role is leading as a player‑coach from day one and grows into a purely leadership role over time. If you don’t want to build a team, this isn’t the right seat.

What You’ll Get

Real ownership at a pivotal stage.

You’re joining as we build the systems to scale from 12 to 50+ people. The strategy function you create will define how the company operates.

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.

We care about what you've actually done, more than whether you check every box. If this sounds like you, but your background doesn’t follow a traditional path, we still want to hear from you.

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