Switchboard is a growing AI product studio for internal operations. 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.

Business Systems

Strategist , you'll figure out how a client's business actually operates, then define what gets built to improve it. 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.

In the full build you own the scope, the requirements sign-off, and the client relationship, working with a Project Manager and Developers. 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. with Claude Code, run the demos, and decide what changes based on how the client reacts.

Map the client's systems and data, decide which system owns what, and define how what we build connects to their tech stack. Translate technical trade-offs Stay involved through build and testing. 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. 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 know when the client needs a full platform and when they need one focused tool and a cleaned-up data model.

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. 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. You've shaped software people use. Strategy and business acumen.

You can explain to a client what AI will and won't do for their team, in language they understand. This could be in consulting, an agency, a product studio, an in‑house product team, or an internal transformation role. Personal projects, tools for your own work, and especially in client or team work.

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 flag risks in writing early enough to act on them.

Experience working with mid-market companies' existing systems (CRMs, ERPs, legacy platforms) and understanding the integration and data migration realities that come with them. Basic SQL or Python skills for quick data analysis or proof‑of‑concepting.

Experience helping non‑technical teams adopt current tools and workflows without overwhelming them. Your strategies and technical direction become the backbone of growing companies' operations. You'll work alongside a tight team that ships real work. Remote‑first. Shape your role in an evolving space at the intersection of business strategy, product, and AI‑powered delivery. built on making others successful, learning every week, and building things that matter.

📌 Business Systems Strategist (Winnipeg)
🏢 Switchboard
📍 Winnipeg