Head of Global Enterprise Customer Success

Job Description

Job Description

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

Canary Technologies is seeking an experienced Head of Global Enterprise Customer Success to own the success of our largest and most strategic global hotel brands. This leader will partner directly with C-suite executives at many of the world's largest hospitality companies, overseeing complex multi-product deployments while driving long-term adoption, retention, and expansion. As the executive sponsor for Canary's most important customer relationships, you will ensure our customers realize measurable business value while helping shape Canary's enterprise customer strategy. You will also lead and develop a high-performing team of Enterprise Customer Success Managers and Enterprise Implementation Managers responsible for delivering exceptional outcomes across our enterprise portfolio.

What You’ll Do

• Own customer outcomes across Canary's largest enterprise accounts, including successful deployments, executive engagement, product adoption, retention, and expansion.
• Build trusted relationships with executive stakeholders—including CIOs, CTOs, COOs, Chief Digital Officers, Commercial leaders, and other senior executives—at the world's largest hotel brands.
• Serve as the executive sponsor for Canary's most strategic customers, proactively managing executive relationships, mitigating risk, resolving escalations, and driving long-term partnership success.
• Lead, coach, and develop a high-performing team of Enterprise Customer Success Managers and Enterprise Implementation Managers, creating a culture of accountability, customer obsession, and continuous development.
• Partner closely with Enterprise Sales to ensure seamless transitions from sales through implementation while supporting long-term account growth and customer success.
• Develop strategic account plans that align customer business objectives with Canary's product roadmap and identify opportunities to expand Canary's footprint across brands, portfolios, and products.
• Collaborate cross-functionally with Product, Engineering, Support, Marketing, and Revenue Operations to advocate for enterprise customer needs and continuously improve the customer experience.
• Establish operational excellence across enterprise implementations by driving scalable processes, governance, and best practices for complex global deployments.
• Define and monitor key success metrics across implementation, adoption, customer health, retention, expansion, executive engagement, and overall customer satisfaction.
• Stay informed on hospitality technology trends and enterprise customer success best practices to continually elevate Canary's strategic customer experience.

What We’re Looking For

• 10+ years of experience in Customer Success, Strategic Account Management, Professional Services, or a related enterprise customer-facing role within B2B SaaS.
• 5+ years of leadership experience building, managing, and developing high-performing customer-facing teams.
• Proven experience serving as the executive relationship owner for Fortune 500 or other large enterprise customers with complex organizational structures.
• Demonstrated success building trusted relationships with C-suite executives and senior business leaders.
• Track record of leading complex, multi-product enterprise software deployments from implementation through long-term customer success.
• Proven ability to drive measurable improvements in customer adoption, retention, expansion, and overall customer health.
• Strong executive presence with exceptional communication, presentation, negotiation, and stakeholder management skills.
• Experience partnering cross-functionally with Sales, Product, Engineering, Support, Marketing, and Operations to deliver customer outcomes.
• Analytical mindset with experience using customer health metrics, business data, and operational insights to drive strategic decision-making.
• Experience within hospitality technology, enterprise SaaS, fintech, or another complex B2B software environment is strongly preferred.

Compensation

Target cash compensation ranges from $201,000 - $259,000, 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.

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.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. 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.