Sales Enablement Manager

About Us

Think about your last hotel stay. Did you skip the front desk line with mobile check-in? Message the staff for extra pillows? Order a late-night snack with a tap on your phone? Then you’ve likely run into Canary in the wild.

Canary Technologies is the leading agentic AI platform for hotel and guest management, powering the digital infrastructure for more than 20,000 hotels in 125+ countries. The world's most renowned hospitality brands, including Marriott International, Four Seasons and Wyndham Hotels & Resorts, partner with us to increase revenue, improve operations and elevate the guest experience.

We’ve executed the largest deployment of autonomous AI systems in hospitality, building technology that fundamentally redefines how guests and hotels interact. It’s made us one of the top-funded hotel technology companies in the world, with nearly $200M raised to date.

Canary has been recognized as a 2024 and 2025 Deloitte Technology Fast 500™ company, Inc. 5000 fastest-growing company, and swept the 2026 HotelTechAwards, including Best Place to Work, #1 Guest Experience Platform, and the Hotelier’s Choice Award. We’re scaling our team to bring innovation to life faster than ever.

We're growing quickly, and we're looking for people who are passionate about their work, want to grow with us and are ready to take on more responsibility along the way. We value rigor and velocity in equal measure: high standards, fast pace, real ownership. If that's the environment you're looking for, this is the place for you.

Come join us! Let’s shape the future of hospitality together.

 

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.

What You’ll Do

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.

What We’re Looking For

• 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.__

Perks & Benefits

We work hard to make Canary a fun, rewarding, and high-energy place to work. Here’s how we take care of our flock:

Time Off

• Unlimited PTO: Take the time you need to truly rest and recharge.
• Holidays + Canary Days: Standard holidays plus monthly company-wide days off for a guaranteed long weekend.
• Birthday Holiday: A dedicated day off to celebrate you!

Travel & Office Flexibility

• Office Exchange: A travel stipend to visit the team in person at our SF, NY, or Dallas hubs.
• Canary Hotel Experience: Staying at a Canary hotel? We’ve got you covered with a credit toward your stay.
• Preferred Hotels Discount: Enjoy a minimum 30% off the best available rate at select partner hotels globally.

Growth & Community

• Self Improvement Club: A monthly budget to help you smash your personal goals.
• Professional Development: Level up your career with a dedicated learning stipend to fuel your skills and cross-functional connection.
• Referral Program: Help us grow the flock and score a cash bonus for successful hires.

  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.