Umang Gupta

Toronto, Ontario · AI Consulting for Legal Teams

Bringing Canadian law firms into the AI age.

I help legal teams adopt AI properly — selecting the right tools, setting up the right workflows, and training people to use them well. Custom-built only where needed, never for its own sake.

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01How I Work

Implementation first. Building second.

Most firms don't need custom software — they need the right tools, set up correctly, and a team that's actually taught to use them. The setup is the easy half.

  1. Assess & select

    Understand how your firm actually works, then choose the AI software that fits — Claude, or whatever suits your practice — rather than forcing a one-size-fits-all tool.

  2. Implement & configure

    Install and configure the tools, connect them to your environment, and design the workflows around them — with data residency and retention settings decided deliberately, not left to defaults.

  3. Train & enable

    Hands-on training for lawyers and staff: structured prompting, verifying output, and folding AI into daily work. This is the piece most rollouts skip — and the reason teams end up struggling with software for years. I've spent a decade as an educator, and I stay until the tools feel natural.

  4. Build only if needed

    Where a genuine gap exists, I build custom tooling. Building is the exception, not the pitch.

02Current Engagement
At an Ontario law firm, I set up Claude for 20 users, trained the team on daily legal workflows, and connected a custom-built CanLII citation-verification server to their AI assistant.
Client name withheld — confidentiality first, always.
03Custom Tools

Built where a real need existed.

Two tools, each built because a client firm needed it — and each designed so the firm stays in control.

CanLII Citation Verification

Stateless MCP Server

A stateless MCP server, hosted on Cloudflare, that lets your AI assistant verify case citations, case IDs, and metadata against the real CanLII database while drafting or reviewing.

Your firm holds its own CanLII API key, and the server handles only public citation lookups — confidential documents never route through it.

How it works

Voice Transcription

Canadian Data Residency

A meeting-note transcription tool for legal teams, built on Google Cloud's Canadian region — data residency is handled in the code, so transcripts stay on Canadian servers.

Learn more
04Beyond AI

The advice doesn't stop at the software.

AI is the way in — not the whole story. For clients with an established relationship, I also consult on the broader business: operations, workflow automation, marketing, analytics, and data modelling.

A decade across product operations, strategy, and training & upskilling means the same person who sets up your AI tools can also help you think through what comes next.

05Questions

What firms ask before working with me.

Does our client data pass through your tools?
The CanLII verification server handles only public citation lookups — case IDs and citation queries. Confidential documents and client information don't route through it. Transcription runs in your firm's own Google Cloud environment, in the Canadian region.
Do you or the AI tools train on our data?
Setups are configured so vendor tools don't use your data for model training, using the no-training and retention controls each vendor provides. I walk your team through exactly what each tool does with your data before anyone uses it.
Which AI tools do you work with?
I'm tool-agnostic. I recommend what fits the firm — so far, Claude has been the right choice for the legal teams I've worked with — but the selection follows your needs, not a reseller agreement.
Do we need our own accounts and API keys?
Yes — deliberately. Your firm holds every vendor relationship: the CanLII API key, the AI subscriptions, the cloud tenant. I set things up inside accounts you own.
Are we locked in if we stop working with you?
No. Because everything runs in your own accounts and infrastructure, ending the engagement doesn't strand you. Documentation and handoff to your IT are part of the work.
Do you replace our IT support?
No — I work alongside your existing IT team or managed service provider. They keep control; I bring the AI-specific expertise.
What does an engagement look like?
Assess, implement, train — and build only where needed. Every engagement is scoped individually; there are no packages, because no two firms work the same way.
Is AI safe for confidential legal work?
It depends entirely on how it's set up — which is exactly why implementation matters. Data residency, retention settings, and access controls are decisions, not defaults. And AI output is probabilistic: anything it produces should be reviewed by a licensed lawyer before you rely on it.
How much does it cost?
Engagements are scoped individually — get in touch and we'll discuss your firm's setup.