AI Onboarding Specialist

Job Title: AI Onboarding Specialist
Saskatoon, SK (office-first)

Business owners buy AI Employees to save time and win customers, but only if the setup works on day one. You get them live, get the answers right, and teach them to run it.

What You’ll Do

You’ll work with AI Automation Specialists, Product, Customer Success and Sales.

• Learn how each new client’s business runs and plan their AI setup


• Build AI Employees, prompts and workflows on our platform


• Test every setup before launch and fix wrong answers


• Lead go-live and train client teams to run it themselves


• Check results after launch and tune what drifts


• Bring common client problems back to Product and your team


• Use AI every day to test, document and move faster

What You’ll Bring

• 2+ years in technical customer success, onboarding or implementation at a SaaS company


• A degree in Business, IT, Computer Science or a related field is an asset


• Hands-on experience setting up chatbots, AI agents or automated workflows for customers


• You write and tune prompts, and can tell why an AI answer went wrong


• You explain technical things simply to people who aren’t technical


• You already use AI in your own work every day

Nice to have: experience running many client onboardings at the same time.

Why Vendasta

Our purpose is simple: make technology easy, accessible and affordable. We’re building the AI workforce for business owners, so the people who run local businesses can spend less time on busywork and more time on their customers. Everything we do starts with those customers. If it doesn’t help a business owner win, we don’t build it.

How We Work
We own it (Drive), we’re candid (Respect), we keep learning (Agility) and we start with the customer (Innovation). We work hard, celebrate each other’s wins, and keep it fun. It’s part of why we were named one of Canada’s Most Admired Corporate Cultures for 2025.

And the coolest part?
We don’t just talk about AI. We build it. Whatever your role, we’ll train you to use it like a power user, with tools most companies are still reading about. Add coaching, mentorship, hands-on workshops and courses that move your career forward, and you’ll grow faster here than anywhere else. Plus, you’ll get health and wellness benefits, flex days and paid volunteer time, because doing your best work means having time for what matters outside it.