Description

About Besty AI

Besty AI is the leading AI-native operating system for the $1T+ short-term-rental and hotel industry. We’re a venture-backed seed stage startup backed by Ridge Ventures, Grand Ventures, and Bungalow Capital.

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 10,000+ properties worldwide with practical AI applications to make their daily lives easier.

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
  • Be part of a fast-growing startup (we’ve doubled in the last 6 months and are among the top quartile of the fastest growing startups on ChartMogul based on 3,000+ companies’ Stripe subscription data)

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/