Business Systems Strategist

About Switchboard

Switchboard is a growing AI 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 replace 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.

About the Role

Are you the person who looks at a 50-step, manual process and thinks, "certainly this could be 5 steps, right?"

As a Business Systems Strategist, you'll figure out how a client's business actually operates, then define what gets built to improve it. Not what to recommend in a deck, but what to build, and why.

Our approach is prototype-first. Most partnerships start with a 2–8 week Jumpstart: discovery interviews, a systems and data audit, and a working prototype that gives the client something real to react to, followed by a build plan. Clients who want to keep going move into the full build, where we turn that prototype into production software their team uses every day. You get real ownership over outcomes by leading strategy throughout. In the Jumpstart you run discovery and build the first version of the prototype. In the full build you own the scope, the requirements sign-off, and the client relationship, working with a Project Manager and Developers.

We run our service delivery primarily in Notion + Claude. Our playbooks for both phases are driven through skills across all stages. You'll work in that system from your first week and help improve it based on your learnings and experiences.

Doing this well takes product fluency, strategy & business acumen, and AI fluency. More on each below.

What You'll Do

• Lead strategic discovery with client stakeholders from frontline staff to C-suite, mapping how work actually moves and where there’s opportunities for efficiency, automation, and AI.
• Define what gets built and why, grounded in what you learned in discovery.
• Build the prototype with Claude Code, run the demos, and decide what changes based on how the client reacts.
• Design the integrations. Map the client's systems and data, decide which system owns what, and define how what we build connects to their tech stack.
• Own the build plan that sequences what gets built and when, so our development team can execute and client leadership stays bought in.
• Translate technical trade-offs into clear narratives that move both CFOs and developers, without getting lost in jargon.
• Turn the prototype into a spec. Work through edge cases with the client's experts, check feasibility with Developers, and own the sign-off.
• Stay involved through build and testing. Keep the build matched to what the client needs, and call scope changes when you see them.
• See it through go-live. Work with our team to train the client's team, partner with the Project Manager on change management, and stay close through hypercare to ensure the new way of working sticks.
• Lead your Business Analyst when certain projects have one. You set the direction for their work, review it, and coach them.

What Success Looks Like

• There's a clear line from your work to the functioning products and automations. Whether it's a prototype, a build plan, or a spec, your output is clear enough that the team can start building without a translation layer in between.
• You pick the right approach, not just the most ambitious one. You know when the client needs a full platform and when they need one focused tool and a cleaned-up data model. Clients trust your judgment because you solve the actual problem, not the most impressive-sounding version of it.
• Prototypes land. The scoping and direction you set consistently validate the right problem and convince clients to move forward.
• Implementation runs on time and on budget because your requirements, workflows, and data models are clear and grounded in reality, and you flag scope changes early instead of letting them pile up.
• Developers want to work with you because the specs you sign off on are well thought out, your technical direction is sound, and you're available when questions come up during the build.
• Clients come back. They ask, "what else can we build together?" because the first engagement actually changed how their team operates.

Who We're Looking For

What the job requires

• Product fluency. You've shaped software people use. You can look at a screen and tell what's working and what to cut, you can work out what a client needs when it differs from what they asked for, and you've written specs that developers built from.
• Strategy and business acumen. You understand how a client makes & spends money and where an operational fix shows up in their numbers. You can put a dollar or hours figure on the impact, and sequence a roadmap against a mid-market budget and how much change the client's team can absorb.
• AI fluency. You already use AI in your own work daily, as a thinking partner for analysis, scoping, and pressure-testing approaches. You know where current models fall short and you check their output before anyone else sees it. You can explain to a client what AI will and won't do for their team, in language they understand. If you're still doing everything from scratch by hand, you'll be slower than the rest of the team.

What you also bring

• 5+ years combining consulting-style discovery with hands-on systems or product work. This could be in consulting, an agency, a product studio, an in-house product team, or an internal transformation role. What matters is that you've led discovery, turned what you learned into clear product direction, and stayed close enough to delivery to know whether your thinking held up.
• You've built things with AI. Personal projects, tools for your own work, and especially in client or team work. You're comfortable working out of a repo with Claude Code, so our delivery setup won't be your starting point. You won't write production code, since our Developers do that, but you will build prototypes yourself.
• You think in systems, not just processes. You can diagram complex workflows and spot bottlenecks quickly. You also see how data flows across an organization and where integrations break down. You're comfortable with relational schemas, API patterns, and modern SaaS, and you understand how data moves between systems and where it gets lost.
• You take ownership. When you find a problem, you work out the cause and bring a recommendation. If it's yours to fix, you fix it and tell people what you did. You flag risks in writing early enough to act on them.
• You can run a room. You're equally comfortable with frontline staff and a CEO asking hard questions about ROI. You ask the right questions, make sure the quieter people get heard, and earn trust with people who've heard a lot of consultants promise a lot of things. When something is off, you say so, to the client or to your own team, and you do it in a way that keeps everyone working on the problem together.
• People don't have to chase you. Clients and teammates know where things stand without asking. Your updates are short and say what happens next, and anyone picking up your work can see what was decided and why.

Nice-to-Haves

• Experience working with mid-market companies' existing systems (CRMs, ERPs, legacy platforms) and understanding the integration and data migration realities that come with them.
• Hands-on experience with APIs, webhooks, or integration tools (n8n, Make, Zapier, or similar).
• Basic SQL or Python skills for quick data analysis or proof-of-concepting.
• Experience helping non-technical teams adopt new tools and workflows without overwhelming them.

What You'll Get

• Real impact. Your strategies and technical direction become the backbone of growing companies' operations. The things you design get built and used.
• Strong team. No layers, rapid decisions, healthy support and collaboration. You'll work alongside a tight team that ships real work.
• Remote-first. Anywhere in Canada with at least 3 hours of overlap with Pacific time.
• Growth opportunity. Shape your role in an evolving space at the intersection of business strategy, product, and AI-powered delivery.
• Culture built on making others successful, learning every week, and building things that matter.
• Competitive compensation, three weeks PTO, and a team that cares about doing meaningful work without burning out.

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.