Customer Success Enablement Manager

About Us

Canary Technologies is changing the game for hotels with modern software powered by Canary's hospitality-specific AI platform.

Canary is utilized by 20,000+ hoteliers in 100+ countries to equip hoteliers with the technology they need to work smarter and wow their guests. Major hotel brands such as Wyndham, Marriott, IHG, Four Seasons, Rosewood, and Best Western trust Canary to deliver results.

Canary was named a 2024 Deloitte Technology Fast 500™ company, a Most Innovative Company by Fast Company and a HotelTechReport Best Place to Work — and is backed by top Silicon Valley investors like Y Combinator, F-Prime, Brighton Park Capital and Insight Partners.

Join us in shaping the future of hospitality!

About the Role

We’re seeking a proactive and driven Customer Success Enablement Manager to join our growing team. In this role, you’ll be instrumental in designing and delivering the training, tools, and processes that empower our CS organization to deliver exceptional customer experiences at scale.

As an Enablement Manager, you’ll support our Customer Success team and work closely with Sales, Product, and Marketing teams to ensure consistent messaging, impactful onboarding, and continuous learning across the organization. Your efforts will directly influence team performance and customer value, establishing you as a key player in shaping the future of how Canary enables success for both our people and our customers.

• Design, deliver, and manage onboarding programs that ramp new CS team members quickly.
• Create and run workshops, product demos, and skills training to improve CS effectiveness.
• Develop ongoing enablement initiatives to keep the team sharp as products and processes evolve.
• Build and maintain playbooks, best practice guides, enablement videos, and internal documentation.
• Partner with CS leadership to create scalable resources that improve team performance.
• Help scale a global CS organization by tailoring enablement programs to fit local contexts while maintaining consistency worldwide.
• Own new hire/team tooling and best practices, ensuring smooth access, documentation, and training.
• Optimize CS processes, workflows, and tools (e.g., Notion, Gainsight, Gong, Salesloft, etc).
• Measure the impact of enablement programs and continuously refine based on feedback and data.
• Drive innovation by embedding AI into team workflows, helping the CS team work smarter and deliver more value.
• Collaborate with Product, Marketing, and Sales teams to ensure CS messaging is consistent, accurate, and up to date.
• Champion knowledge-sharing and foster a culture of continuous learning within the CS org.

• 2–4+ years in Customer Success, Enablement,  or a similar role.
• Proven experience building training, playbooks, or enablement content for customer-facing teams.
• Strong presentation and communication skills; able to engage and inspire teams.
• Excellent facilitation and workshop leadership skills.
• Strong project management skills with the ability to prioritize and execute effectively.
• Familiarity with CS methodologies and tools (e.g., Gainsight, Salesforce, customer health scoring).
• Highly organized, analytical, and comfortable in a fast-paced startup environment.
• A collaborative, proactive mindset with a passion for helping others succeed. Self-starter who thrives in a dynamic, often ambiguous environment.

We also work hard to ensure Canary is a fun and exciting place to work! Here are some of the additional benefits:

Canary Days:  As a company we want to ensure that the team has time to recharge. Each month we provide company wide days off to ensure there is at least one extended weekend or day off.

Self Improvement Club: We meet each month and share our personal goals for the month. Each individual is provided a budget towards any purchases that help us achieve these goals.

Professional Development Chats: We provide budget to help drive cross functional professional development conversations across the organization.

Travel Reimbursement: Team members are able to visit our offices across New York, San Francisco or Dallas when they choose, and are provided a travel stipend for doing so.  Spend time working with the team in their office, and use the rest of your time exploring a new city!

Personal Travel Reimbursement: If you stay at a hotel that Canary works with, we provide a credit towards your stay.

Canary Technologies is an equal opportunity employer. We recruit, employ, train, compensate and promote talent regardless of race, religion, ethnicity, national origin, citizenship, gender, gender identity, sexual orientation, age, veteran status, disability, genetic information or any other protected characteristic.