About the Position

Customer Success Enablement Manager

New York, NY

Full Time / Hybrid

About Us

Canary Technologies is revolutionizing the hospitality industry with its modern software powered by AI. Trusted by over 20,000 hoteliers in 100+ countries, Canary's platform helps hotels work smarter and delight their guests. Major hotel brands such as Wyndham, Marriott, IHG, Four Seasons, Rosewood, and Best Western rely on Canary for exceptional results.

Canary was recognized as a 2024 Deloitte Technology Fast 500™ company, a Most Innovative Company by Fast Company, and a HotelTechReport Best Place to Work. Backed by top Silicon Valley investors, Canary is on a mission to shape the future of hospitality.

Join us in shaping the future of hospitality!

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.

Requirements

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.

We Offer

Compensation

Target cash compensation ranges from $107,000 - $120,000, including a fixed annual salary and a performance-based bonus paid quarterly.
This role also includes a stock option grant, subject to board approval.
Actual compensation will be commensurate with the candidate's skill level, experience, and specific work location.

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 a 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.

Company Commitment

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.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

About the Company

Canary Technologies is at the forefront of transforming the hospitality industry with cutting-edge software powered by AI. Our platform is trusted by over 20,000 hoteliers in 100+ countries, enabling hotels to work smarter and provide exceptional guest experiences. Major hotel brands such as Wyndham, Marriott, IHG, Four Seasons, Rosewood, and Best Western rely on Canary to deliver outstanding results.