Sales 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 looking for a Sales Enablement Manager to own how our sales team learns — from day one onboarding through ongoing skill development across every seller in the org. In this role, you'll build and run the full ramp experience for every new sales hire, and design the "everboarding" programs that keep our tenured reps sharp as our product, customers, and playbooks evolve. You'll partner closely with Sales Leadership, Product, Marketing, and Customer Success teams to translate institutional knowledge into scalable training, playbooks, and certifications that measurably improve how our team sells. This is a foundational role: your work will directly shape how quickly new reps hit quota, how consistently the team executes our motion, and how Canary builds a durable culture of learning as we scale. Responsibilities Onboarding & New Hire Ramp Own the end-to-end onboarding and ramp experience for every new sales hire — from pre-boarding through fully ramped — including curriculum design, learning paths, milestones, and ramp-time targets. Build structured, measurable onboarding programs with clear competency checkpoints, certifications, and graduation criteria so we know exactly when a new rep is ready to carry quota. Continuously iterate on the onboarding experience based on new hire feedback, manager input, and ramp-time data; reduce time-to-productivity quarter over quarter. Everboarding & Skill Development Design and run "everboarding" programs that keep tenured reps growing — recurring skill-building sprints, deep-dive workshops, role-based learning tracks, and certification refreshes tied to product and process changes. Identify capability gaps across the team through call reviews, win/loss analysis, and partnership with sales leadership; build targeted upskilling programs to close them. Develop and maintain a sales competency framework that defines what “good” looks like at each level (SDR, AE, Senior AE, etc.) and powers career development conversations. Playbooks & Institutional Knowledge Own, build, and continuously improve the sales playbook library — capturing how we run discovery, demos, multi-threading, objection handling, negotiation, and every other repeatable motion. Codify institutional knowledge from top performers into reusable resources so best practices spread across the team instead of staying tribal. Maintain a single source of truth for sales messaging, positioning, competitive intel, and product knowledge; ensure content stays accurate as the product and market evolve. Cross-Functional Alignment Partner with Product and Marketing teams to ensure sales messaging, positioning, and product knowledge stays consistent and current across the team. Partner with Customer Success team on handoff processes and post-sale enablement so the customer experience stays seamless from first call through renewal. Champion knowledge-sharing rituals across the sales org and tailor enablement to a globally distributed team while maintaining consistency across regions and markets. Qualifications 2–4+ years in Sales Enablement, L&D, or a similar role with significant ownership of onboarding or training programs for sellers. Demonstrated experience building a new hire sales onboarding program from scratch or substantially overhauling one — bonus if you can speak to measurable ramp-time improvements. Track record of designing ongoing training, certification, or skill-development programs for sales teams. Strong instructional design instincts — you know how adults learn and can build curriculum that actually changes selling behavior, not just slides that get clicked through. Excellent facilitation, presentation, and workshop leadership skills; comfortable role-playing and coaching reps live. Familiarity with modern sales methodologies (MEDDIC, Command of the Message, Challenger, etc.) and the tools that support them (Gong, Salesforce, Salesloft/Outreach). Strong project management; you can run multiple programs in parallel and ship on a timeline. Analytical mindset — comfortable defining success metrics for enablement programs and using data to iterate. Self-starter who thrives in a fast-paced, often ambiguous startup environment. A collaborative, proactive operator with genuine passion for helping reps grow. Compensation The base salary range for this role is $92,000 - $102,000. I n addition to base salary, this position is eligible for a performance-based bonus paid monthly, with a target of $15,000 - $18,000 annually. This brings the total expected cash compensation range to $107,000 - $120,000. Compensation is subject to standard withholding and applicable taxes. Actual compensation will be commensurate with the candidate’s skill level, experience, and specific work location. This role may also include the opportunity to earn equity. 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.