Sales Enablement & Operations Specialist

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

This role is 70% Training & Enablement and 30% Sales Operations, ideal for someone who thrives at the intersection of people development and process optimization. You will play a pivotal role in ensuring our sales team is fully equipped with the knowledge, resources, and processes needed to drive success in a fast-paced, high-growth environment.

• Design, deliver, and manage onboarding programs for new sales team members
• Develop ongoing enablement content, including playbooks, best practice guides, and product updates
• Work with local sales leaders to adapt global enablement content to local languages and market needs
• Lead workshops, product demos, and skills training to improve sales effectiveness
• Partner with Product, Marketing, and Customer Success teams to ensure sales messaging is consistent and up-to-date
• Support CRM hygiene and reporting to provide accurate pipeline and forecasting data
• Analyze sales performance metrics to identify trends and recommend improvements
• Assist in optimizing sales processes, tools, and workflows to drive efficiency
• Collaborate with leadership to implement operational improvements that scale with growth

• 2–4 years of experience in sales enablement, training, or sales operations (SaaS or hospitality tech experience preferred).2 years of experience as Account Executive
• Strong presentation and communication skills; ability to engage and inspire sales teams
• Proficiency with CRM tools (Salesforce or Salesloft) and enablement platforms
• Highly organized, analytical, and comfortable working in a fast-paced startup environment
• We value self-starters who thrive in collaborative but fast-moving, often ambiguous environments

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.