Matt Stark is an agentic and Microsoft 365 architect. He plans and builds what AI depends on: second brains, secure Microsoft 365 and Azure environments, and the migrations that get information there. He works directly with the leaders who own the result, from the Greater Toronto Area and remotely.
See the outcomesFor a startup, Matt worked with the founders on the platform architecture and a multi-agent, test-driven build harness they now use to test and release. The platform runs on Azure with MCP and role-based access.
For a national insurer, AI helped reverse-engineer a document system older than the web from its manuals and code, then build the migration tool, its automated tests and Power BI oversight.
The same insurer's website content was converted by a purpose-built transpiler, then migrated in two weeks with no specialist needed.
Claude and Codex build this website from its maintained wiki, carrying work forward with less repeated input from Matt.
An AI decision reaches beyond the model: the information has to be useful, access has to match the work, and the result has to fit the systems your team relies on. Matt brings those concerns into the same conversation.
Current AI work rests on hands-on delivery across collaboration, automation, security, migrations and software.
Discovery, architecture, estimates and statements of work for business and technical teams.
Stepping into projects that need escalation or rescue, and finding the cause as well as the fix.
Mentoring developers, and hiring and leading delivery teams on larger programmes.
A startup platform and its multi-agent build harness; AI-assisted migrations for a national insurer.
A utility's field training platform on Microsoft 365, Power Platform and Teams, from workshops to hiring and leading the developers.
Independent practice across agentic systems, Microsoft 365, security, migrations and business applications.
Engineering director and chief architect roles, and consulting for law firms, financial services, energy and the public sector.
The choice starts with the work, the information and the systems your team already uses.
You work directly with Matt on the decisions that shape the project. He delivers a focused scope, brings in contractors when more hands are needed, or plans and shadows delivery by a larger firm.
Packaged starts for a second brain, or planning support for a larger programme. Every project is scoped on a call.
A maintained knowledge base in SharePoint Online that Microsoft 365 Copilot and your people answer from.
A repository-based second brain your agents work from. Two weeks gets you to first base; then your team operates it, or Matt supports it.
A second brain on AWS Bedrock or Azure AI Foundry, with the data connections and identity mappings an enterprise needs. About six weeks.
At enterprise scale, Matt plans the work and shadows delivery while a larger firm implements, so the decisions stay sound through the build.
Bring a process that takes too much effort, a project that has stalled or an idea you want to test. Remote first from the Greater Toronto Area, and in person across Toronto, Mississauga and the Golden Horseshoe when that helps.
References and a full resume are available on request, and the legal second brain can be shown live on a call.
A call is enough to find a useful next step.
