Sales Enablement & Operations Specialist

Summary

Join Canary Technologies, a fast-growing hospitality tech company, as a Sales Enablement and Operations Specialist. This role blends training and enablement (70%) with sales operations (30%), requiring expertise in both people development and process optimization. You will design and deliver onboarding programs, create enablement content, conduct workshops and training, and collaborate with various teams to ensure consistent sales messaging. The position also involves supporting CRM hygiene, analyzing sales performance, optimizing sales processes, and implementing operational improvements. Canary offers a dynamic startup environment and various benefits, including monthly company-wide days off, a self-improvement budget, professional development funds, and travel reimbursements.

Requirements

• 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

Responsibilities

• 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

Preferred Qualifications

We value self-starters who thrive in collaborative but fast-moving, often ambiguous environments

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