Sharp Decisions jobs

Location: Toronto (hybrid)

Compensation: $75,000 – $100,000 CAD

Type: Full-time | Two positions available

AI is rewriting the rules of legal practice. We're not watching — we're building.

CV Labs is the product and growth studio inside CanadaVisa, Canada's immigration engine. Our ecosystem reaches 1.5 million visitors per month, powers the country's largest immigration peer community (~1M members), processes thousands of cases per year, and delivers personalized guidance to 180,000+ registered users. We have distribution that most startups would kill for — and the engineering team to do something extraordinary with it.

We're building an AI-native law firm. Our lawyers don't just serve clients — they collaborate with engineers to automate their own workflows, shape the product roadmap, and push the limits of what AI can do in a regulated practice. The goal isn't to use technology to make lawyers 10% faster. It's to rethink from first principles how legal services are delivered, who can access them, and what a legal career looks like in 2026 and beyond.

We are backed by 30 years of infrastructure, a dominant market position, and a team that ships like a startup. Think of us as the best parts of a rocketship with the revenue base of an institution.

The Opportunity

A recent legislative change has unlocked a massive new segment of Canadian immigration — one that potentially affects millions of people who don't yet know they're eligible. We're already capturing this wave — and building the product infrastructure to serve it at ten times the scale. We need operational talent who can ensure every client file moves through the pipeline with speed, precision, and care.

The Role

We've built an AI-powered platform that does most of the heavy lifting on every client file — extracting data from documents, cross-validating information across records, auto-filling government forms, and flagging edge cases. Roughly 80% of the work is handled before you ever see a file.

Your job is the other 20%. You're the human judgment layer between our technology and our clients. You review what the system flags, catch what it can't, keep clients informed throughout their journey, and make sure every file that goes out the door is flawless. When a file is clean, your review takes minutes. When it's not, you're the one who figures out why and drives it to resolution.

This is not a traditional case management role. You'll work inside a purpose-built dashboard alongside AI that gets smarter every week — and you'll be one of the people making it smarter.

What You'll Do

Review files at speed. Use our AI-powered dashboard to process client applications. The system pre-validates documents, checks for inconsistencies, and auto-fills forms. You focus on the flags — the graceful bypasses, the name discrepancies, the edge cases the system escalates for human judgment.

Be the client's guide. You're the main point of contact for clients via our in-platform messaging system. They're navigating an unfamiliar process and they need someone who is warm, responsive, and clear. You'll answer questions, explain next steps, and keep files moving — targeting a one-day response time.

Manage volume. You'll carry a high-volume caseload across multiple stages — from eligibility review through government submission and beyond. Prioritization and triage are second nature to you.

Escalate with context. When a file hits a complex legal question, you package it with the right context and hand it to our attorneys. Good escalations save everyone time — you'll learn quickly what warrants a flag and what you can resolve yourself.

Spot what can be automated. Every time you repeat a task, ask whether it should exist. You'll work closely with our product team to identify patterns, suggest improvements, and help eliminate work that the system should be doing instead of you.

See files through to the finish. Track applications from submission through government decision. Verify signed documents, manage follow-ups, handle dormant files, and be the one to deliver the good news when an application is approved.

Who You Are

Experienced in operations. You have 1–3 years in an operations, client services, or process-intensive role. Backgrounds at companies like Stripe, Deel, Shopify, or similar high-growth environments are great — but we care more about how you think than where you've worked. Recent graduates with the right instincts should apply.

Detail-obsessed. You catch the thing everyone else misses. A name spelled two different ways across documents, a date that doesn't add up, a checkbox that shouldn't be checked — these things jump out at you.

A strong written communicator. About a quarter of your time will be spent messaging clients. Your tone needs to be warm, clear, and confident. You can explain a complicated situation in plain language and make someone feel like they're in good hands.

A systems thinker. When you solve a problem twice, you ask why it isn't automated. You don't need to write code, but you think in workflows, bottlenecks, and repeatable processes.

AI-curious. You've used ChatGPT, Claude, or similar tools and you've thought about what they mean for how work gets done. You're excited — not threatened — by working alongside AI every day.

French proficiency is a plus — some client documents are in French, and bilingual communication is an asset.

No legal or immigration experience required. We'll teach you what you need to know. We'd rather hire someone with sharp operational instincts and train them on the domain than the other way around.

Compensation & Benefits

• Salary: $75,000 – $100,000 CAD

• Vacation: Flexible — take what you need. We care about what you ship, not when you're at your desk.

• Benefits: Competitive health, dental, and wellness coverage.

• Reports to: Chief Growth Officer

Why CV Labs

You'll join a small, high-caliber team with a front-row seat to what happens when AI meets a real legal practice at scale. The work is tangible — real clients, real files, real outcomes — and the mandate is to make it radically better every week. There's room to grow as we grow, and you'll have direct access to leadership from day one.

If you're the kind of person who finds inefficiency physically painful and wants to work somewhere that actually does something about it — we'd like to meet you.