Guest Communications Manager

About the Company

Besty AI is developing an AI-driven operating system for the hospitality sector. The company helps short-term rental and hospitality teams handle guest communication more quickly, resolve issues more effectively, and improve the guest experience without having to grow large support teams. It is supported by leading investors in AI and technology, including backers associated with Discord, Perplexity, and the Stanford and Berkeley AI labs.

Role Overview

Besty AI is looking for a Guest Experience AI Specialist to support guest conversations in partnership with its AI systems. In this role, you will step in when human judgment is needed, make decisions in real time, and help train the AI so performance improves continuously. The position combines guest service, operations, and AI training, and offers growth into broader responsibilities in operations, customer success, product, or AI quality.

Key Responsibilities

• Take over guest messages whenever the AI requires human support.
• Audit AI-led conversations and fix errors or gaps in responses.
• Show the system what the correct action should have been when it gets stuck.
• Keep communication friendly, prompt, precise, and aligned with hospitality standards.
• Partner closely with product and operations teams to improve the AI each week.
• Own complicated issues and convert recurring problems into scalable processes.

What We’re Looking For

• A person who is ambitious and thrives in a fast-moving startup setting.
• Excellent written communication skills.
• A calm, warm, and professional style when dealing with guests.
• Strong attention to detail and dependable follow-through.
• Ability to manage several tasks at the same time.
• A knack for identifying patterns and explaining root causes.
• Interest in artificial intelligence and enthusiasm for using it daily.
• Comfort with software tools and adapting to new systems quickly.
• Motivation to take on responsibility, move quickly, and work to high standards.

Preferred Background

Experience in hospitality, customer support, property management, or short-term rentals is helpful, but not mandatory.

Compensation and Benefits

The role offers annual compensation in the range of $60,000 to $70,000, along with equity and health insurance. Additional benefits include a downtown Toronto office, free breakfast and lunch every day, and unlimited snacks and drinks.

Growth Opportunity

This position is designed as a launchpad for someone who wants to grow quickly. Over time, it can open doors into leadership and expanded responsibilities within a high-growth AI startup.