Overview
Guest Communications Manager at AI Startup Jobs in Toronto, Ontario, Canada at Besty AI
Title: Guest Communications Manager at AI Startup
Company: Besty AI
Location: Toronto, Ontario, Canada
Company: Besty AI
Type: Full-time, in-person
Compensation: $60-70k plus equity, health insurance
Other perks: Downtown Toronto office, free breakfast and lunch every day, unlimited snacks and drinks
Besty is building the AI operating system for hospitality.
We help short-term rental and hospitality operators respond to guests faster, solve issues more efficiently, and deliver a better guest experience without needing to scale huge support teams.
We are backed by top AI and technology investors, including investors behind Discord, Perplexity, and the Stanford and Berkeley AI labs. We are an ambitious, fast-moving team building in one of the most important technology shifts of our time.
We are looking for people who want to grow quickly, take on real responsibility, and be part of a company with very high expectations and very high upside.
The role
We’re hiring a Guest Experience AI Specialist to help manage guest conversations alongside our AI.
You will respond to guests when the AI needs help, make judgment calls in real time, and teach the AI so it gets better over time.
This role is part guest experience, part operations, and part AI training.
The right person will use this role as a launchpad to grow into a larger role in operations, customer success, product, or AI quality.
You will:
- Respond to guest messages when the AI needs human help
- Review AI conversations and correct mistakes
- Teach the AI what it should have done when it got stuck
- Keep responses warm, clear, fast, and hospitality-focused
- Work directly with product and operations to make the AI better every week
- Take ownership of messy problems and turn them into repeatable systems
What we're looking for
We’re looking for someone who is hungry, sharp, and wants to move up in their career:
- Ambitious and excited by a fast-paced startup environment
- A strong written communicator
- Warm, calm, and professional with guests
- Detail-oriented and reliable
- Comfortable juggling multiple tasks at once
- Good at spotting patterns and explaining what went wrong
- Curious about AI and excited to work with it every day
- Comfortable using software tools and learning new systems
- Energized by responsibility, speed, and high expectations
Hospitality, customer support, property management, or short-term rental experience is a plus, but not required.
Why join Besty
This is a chance to join a fast-growing AI startup early. For the right person, this role can grow quickly and expand into leadership roles in our fast-growing startup.
You’ll work with an ambitious team, learn quickly, and get exposure to how AI products are built, improved, and deployed in the real world.
