About the Position

Sales 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 to deliver 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 like Y Combinator, F-Prime, Brighton Park Capital, and Insight Partners, Canary is at the forefront of hospitality technology.

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 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.

Requirements

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

*Target cash compensation ranges from $107,000 - $120,000, including a fixed annual salary and a performance-based bonus paid monthly.

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.*

We Offer

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.

About the Company

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.

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Sales Enablement Manager

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Job Description, Responsibilities & Requirements