Head of Strategy

About the role

At Switchboard, we help mid-market companies fix how they work, not just talk about it. We combine workflow design, modern software, data integration, and AI automation to turn messy operations into something that actually runs.

We're ready for someone to own the strategy function. This is a player-coach role that grows alongside the business. You'll be the person clients trust most when they're thinking about how their business should run in the next 2-3 years, and the person our team looks to for guidance on how to get them there. You'll inherit a function the founders built from scratch, and you'll have the runway to make it yours.

What you'll do

• Lead and grow the team: Manage four Business Systems Strategists today, with room to grow alongside the team. Set clear expectations, give real feedback, and build a culture where people challenge each other's thinking and keep sharpening their craft. You're the escalation point when client situations get tricky.
• Stay close to the work: Own one or two strategic client accounts so your judgment stays grounded. Join key sessions with your team to understand how businesses actually run, where they break, and what's possible. You're not here to review decks from a distance. You're in the room, thinking on your feet, helping your team and their clients see a path forward in real time.
• Own the quality bar: Review your team’s discovery plans, system designs, and roadmaps before they go to clients. Partner with Project Managers and Developers to ensure that what we promise and what we ship actually line up.
• Build methods, not one-offs: Turn good projects into reusable playbooks, templates, and frameworks. Standardize how we do discovery, process mapping, and requirements and ensure your team is aligned and adopting them successfully.
• Shape the offering: Keep a pulse on where AI, no-code, low-code and integration tools are going. Identify patterns across clients to spot opportunities for new services or internal accelerators.

What Success Looks Like

Within 12-18 months:

• Strategists produce work that technical teams respect and can actually build from.
• Clients describe Switchboard as "the team that actually understands how our business runs".
• Roadmaps are realistic, phases land, and projects avoid painful surprises.
• There's a clear, repeatable way we do discovery and process design, not "every strategist does it their own way".
• Strategy work is profitable without being rushed.
• Your team feels challenged, supported, and clear on how they can grow.

Who we're looking for

• 7+ years in consulting/agency in business systems, operations consulting, or digital transformation, serving mid-market clients. You've led discovery, mapped processes, designed solutions, and seen them through to implementation and change management rollouts.
• You’ve worked with modern mid-market tech stacks: Think platforms like Airtable, Retool, or n8n. You're not coming from strictly enterprise data warehouses and custom dev. You've worked in SaaS environments and understand their integration and customization tradeoffs.
• Player-coach experience. You've managed a small team while still carrying a light client workload. You've given hard feedback, developed people, and maybe built internal methods or playbooks along the way.
• Strong process and systems thinking. You can walk into a messy workflow, map it clearly, and design a future state that accounts for people, tools, and data. You think in MVPs and roadmaps, not just recommendations.
• Technically fluent. You’re not a developer, but you understand data. Comfortable with relational schemas, APIs, and how information moves across CRMs, ERPs, and custom tools. You know what makes a system fragile versus scalable.
• Practical AI and automation experience. You've used Zapier, Make, n8n, or custom integrations to remove manual work. You know where AI helps in a workflow or department and where it's noise.
• Can run a room. You're the one clients want in the room when it matters. Comfortable facilitating with frontline staff or C-suite, thinking on your feet when the conversation shifts, and explaining trade-offs in plain language.
• Excited to build, not just run. You see a 4-person team and think about what it looks like at 10. You want to shape how this function operates, not just manage what's already there.
• Bias for action. Comfortable deciding with incomplete information, then iterating as reality shows up.

Why You'll Love This Role

What you'll get

• Real influence: Shape how mid-market companies design their operations and how Switchboard delivers strategy as we grow.
• Direct collaboration with the CEO on strategy and execution. No layers, fast decisions.
• Remote-first: Anywhere in Canada with 3-hour overlap with Pacific time working day.
• Growth: A clear path to build out the Strategy function, grow into broader leadership, and shape how Switchboard operates as we scale from 15 to 50+.
• Compensation: Competitive salary, benefits, and real time off to recharge.