Customer Success Associate

Location: Toronto

Besty Overview

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.

This is a fully in-person role at our office in Toronto.

Position Overview

Reporting to the Head of Customer Success, the Customer Success Associate will be responsible for owning customer relationships post-sale and ensuring customers realize value quickly and consistently from Besty. This person will serve as a trusted partner to operators, managing onboarding, adoption, and ongoing success while acting as the voice of the customer internally.

Key responsibilities will include:

• Customer Success & Retention: Own a portfolio of customers post-onboarding, serving as their primary point of contact. Drive retention and expansion by proactively identifying risks, addressing issues, and ensuring customers achieve their desired outcomes using Besty.
• Onboarding & Adoption: Assist with live onboarding sessions, account setup, and early product adoption. Help customers reach go-live smoothly by guiding them through core workflows and best practices.
• Product Expertise: Maintain deep knowledge of Besty’s product and roadmap. Guide customers through features, workflows, and best practices, handling both tactical and strategic questions with an operator-first mindset.
• Customer Insights: Surface high-signal customer feedback, feature requests, and usage insights to inform roadmap prioritization and product improvements.
• Operations & Process: Maintain accurate customer data, health tracking, and success metrics within internal systems. Contribute to the development and refinement of customer success playbooks, documentation, and workflows as the Company scales.
• Special Projects: Support ad-hoc projects related to onboarding, customer experience, and operational improvements as the Company scales.

Professional Qualifications

An ideal candidate will be someone who has:

• Demonstrated ability to manage customer relationships and drive successful outcomes

• Strong communication skills with comfort interfacing directly with customers

• High ownership mentality with strong attention to detail and follow-through

• Ability to operate effectively in a fast-paced, ambiguous, startup environment

• Strong organizational and time-management skills

• Specific knowledge of hospitality, proptech, or vertical SaaS is a plus

Personal Characteristics

Other traits we desire in this candidate include:

• A natural leader who can influence and inspire others. 
• Entrepreneurial with a high level of energy, dedication, and an unrelenting drive to succeed and win. 
• A strategic thinker who is insightful, creative, curious, and experienced in crafting and executing a high velocity strategy for rapid growth. 
• Clear communicator - proven ability to build influence across all levels of the organization and with key vendors and customers. 
• Inspires a culture of innovation, execution, collaboration, and accountability.

Next Steps

If you believe you are a strong fit for this role, please submit your application and optionally reach out directly to the hiring manager with a concise overview of your background and interest in the position.

Hiring Manager: Head of Customer Success

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