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.

Senior Technical Customer Support Agents handle more complex customer issues and act as a bridge between frontline Support, Support leadership, Product, Engineering, Customer Success, and Ops. This role owns advanced troubleshooting, sensitive customer handling and de-escalation, clean internal documentation, and strong escalations. L2 Associates also mentor L1 teammates and help improve support workflows, documentation, macros, and escalation quality.

• Product & Technical Expertise: Handle moderately complex product questions, configurations, integrations, and edge cases using account context and product knowledge.
• Problem Solving & Troubleshooting: Own escalated issues through structured investigation using ticket history, documentation, internal tools, logs/data, and evidence.
• Communication: Communicate complex or sensitive issues clearly and reassuringly to customers, L1 teammates, and internal partners; de-escalate frustrated customers with empathy, ownership, and clear next steps.
• Operational Execution: Manage complex, on-hold, engineering-dependent, or cross-functional tickets with clean notes, proactive follow-up, and clear ownership.
• Continuous Improvement:
  • Identify and address gaps in documentation, macros, workflows, tooling, escalation paths, or product behavior.
  • Flex project management skills for small work streams such as documentation updates, escalation improvements, or issue-pattern tracking.
  • Use approved AI tools responsibly to improve speed, quality, consistency, and customer effort.
• Uphold team standards: Show up and demonstrate integrity, reliability, adaptability, collaboration, and ownership of your work everyday.

• 3+ years experience supporting customers by phone, in addition to email and chat.
• Proven experience in technical customer support, ideally in B2B SaaS, hospitality technology, or another complex product environment.
• Ability to communicate complex technical or workflow issues clearly to customers, teammates, and internal partners, including sensitive customer de-escalation.
• Strong troubleshooting and critical-thinking skills, including ability to separate symptoms from root cause.
• Strong documentation habits and ability to create clear internal notes, escalation summaries, and knowledge updates.
• Experience creating internal documentation, macros, playbooks, or escalation templates.
• Ability to manage competing priorities, follow up proactively, maintain ownership of complex work, and coordinate small work streams with clear owners and next steps.
• Collaborative mindset with a willingness to mentor peers and raise the technical bar of the frontline team.
• Multilingual communication skills or experience supporting customers in multiple languages is a strong plus.
• Experience with Zendesk, monitoring/logging tools, PMS/integration workflows, or hospitality systems (preferred).
• Experience partnering with Product, Engineering, CS, Ops, or Support leadership (preferred).
• Familiarity with AI-enabled support workflows or responsible AI/tool usage (preferred).

Target cash compensation ranges from $70,000 - $95,000, 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.

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.