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 looking for a Customer Success Enablement Manager to own how our CS team learns — from day one onboarding through ongoing skill development across the org. In this role, you'll build and run the full ramp experience for every new CS hire, and design the "everboarding" programs that keep our tenured team sharp as our product, customers, and playbooks evolve. You'll partner closely with CS leadership, Product, Sales, and Marketing to translate institutional knowledge into scalable training, playbooks, and certifications that measurably improve how our team shows up for customers. This is a foundational role: your work will directly shape how quickly new hires reach productivity, how consistently the team executes, 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 CS 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 hire is ready to own accounts. 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 CSMs 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 skills assessments, call reviews, and partnership with CS leadership; build targeted upskilling programs to close them. Develop and maintain a CS competency framework that defines what good looks like at each level and powers career development conversations. Playbooks & Institutional Knowledge Own, build, and continuously improve the CS playbook library — capturing how we run renewals, expansions, escalations, executive business reviews, onboarding handoffs, 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 CS processes, methodologies, and customer-facing materials; ensure content stays accurate as the product and motion evolve. Tools, Process & Measurement Own CS team tooling (Notion, Gainsight, Gong, Salesloft, Salesforce, etc.) — access, enablement, adoption, and best practices. Embed AI into team workflows to help CSMs work smarter and scale their impact. Measure the impact of every onboarding and enablement program against clear metrics — ramp time, certification rates, skill progression, program NPS — and use the data to refine. Cross-Functional Alignment Partner with Product, Marketing, and Sales to ensure CS team messaging, positioning, and product knowledge stays accurate and current. Champion knowledge-sharing rituals across the CS org and tailor enablement to a globally distributed team while maintaining consistency. Qualifications 2–4+ years in Customer Success Enablement, L&D, CS Operations, or a similar role with significant ownership of onboarding or training programs. Demonstrated experience building a new hire 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 customer-facing teams. Strong instructional design instincts — you know how adults learn and can build curriculum that actually changes behavior, not just slides that get clicked through. Excellent facilitation, presentation, and workshop leadership skills. Strong project management; you can run multiple programs in parallel and ship on a timeline. Familiarity with CS methodologies, tools (Gainsight, Salesforce, Gong), and customer health frameworks. 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 teammates grow. Compensation The base salary range for this role is $92,000 - $102,000 . In addition to base salary, this position is eligible for a performance-based bonus paid quarterly, 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.