Skills

Leadership Go Sales Training

Job Specifications

About Besty AI

Besty AI is the leading AI-native operating system for the $120B hotel and short‑term‑rental industry. We’re a venture-backed seed stage startup backed by Ridge Ventures, Grand Ventures, and Bungalow Capital Management.

We’ve raised over $4M from the heads of the Stanford & Berkeley AI labs and investors behind Discord, Fastly, Hugging Face, Covariant, and Replicate.

Besty was founded by a property manager who scaled from 0 to 30 listings in under 10 months, an AI scientist from Yale, and an all-star team of software engineers obsessed with shipping a product loved by hundreds of paying hosts. We’re proud to serve over 30,000 properties worldwide across 20 different countries.

About the Role

We’re hiring an Onboarding Specialist who’s ready for outsized ownership and velocity. You’ll run high-quality live onboarding sessions, optimize each account, guide customers through new features, handle tactical questions, and serve as their early-stage partner. Your work directly impacts retention, expansion, and how we scale the market.

This is a fully in-person role in Toronto, Ontario.

What You’ll Do

Run high-leverage live onboarding sessions with key customers and create immediate, measure ROI and set the tone for a long-term partnership
Configure customer accounts end-to-end and guide customers through the product, delivering hands-on training that matches their goals and existing workflows
Keep customers current on new features and best practices, handling Q&A with an operator-first mindset
Act as the primary point of contact during and after onboarding, proactively unblocking issues and ensuring every new customer reaches go-live as quickly and smoothly as possible
Surface valuable customer insights to Engineering and the Head of Onboarding to influence product direction
Build deep product expertise and continuously refine our onboarding playbooks, documentation, and checklists as the product evolves and the customer base scales

What’s In It For You?

Equity, competitive salary, and commission
Growth opportunity into a leadership role
A seat on an elite customer experience team in a rapidly scaling environment
Own meaningful outcomes as we grow from Seed to Series A and beyond

Don't just apply to the role... send a personal message, follow up, use a multi-threaded approach. Stand out.

Message our Head of Sales directly: https://www.linkedin.com/in/edwardshorterr/