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About the Role
Senior Technical Customer Support Agents handle complex customer issues, acting as a liaison between frontline support, leadership, Product, Engineering, Customer Success, and Operations. This role involves advanced troubleshooting, sensitive customer handling, de-escalation, internal documentation, and managing escalations. L2 Associates also mentor L1 teammates and contribute to improving support workflows, documentation, macros, and escalation quality.
Responsibilities
- Handle moderately complex product questions, configurations, integrations, and edge cases using account context and product knowledge.
- Own escalated issues through structured investigation using ticket history, documentation, internal tools, logs/data, and evidence.
- 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.
- Manage complex, on-hold, engineering-dependent, or cross-functional tickets with clean notes, proactive follow-up, and clear ownership.
- Identify and address gaps in documentation, macros, workflows, tooling, escalation paths, or product behavior.
- Utilize 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.
- Demonstrate integrity, reliability, adaptability, collaboration, and ownership of work daily.
Requirements
- 3+ years of experience supporting customers via phone, email, and chat.
- Proven experience in technical customer support, ideally in B2B SaaS, hospitality technology, or a complex product environment.
- Ability to communicate complex technical or workflow issues clearly to customers, teammates, and internal partners.
- Skill in sensitive customer de-escalation.
- Strong troubleshooting and critical-thinking skills, including the 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.
- 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 is preferred.
- Experience partnering with Product, Engineering, CS, Ops, or Support leadership is preferred.
- Familiarity with AI-enabled support workflows or responsible AI/tool usage is preferred.
Skills
- Technical Customer Support
- B2B SaaS
- Hospitality Technology
- Complex Product Support
- Troubleshooting
- Critical Thinking
- Documentation
- Communication
- De-escalation
- Project Management
- AI Tools
- Zendesk
- Monitoring Tools
- Logging Tools
- PMS Integration
- Hospitality Systems
Location
- SF
- NY
- Dallas
Work Type
- Full-time
Experience Level
- Senior
- 3+ years
Salary/Compensations
- $70,000 - $95,000
- Includes a fixed annual salary and a performance-based bonus paid quarterly.
- Stock option grant, subject to board approval.
- Actual compensation will be commensurate with the candidate's skill level, experience, and specific work location.
Benefits
- Unlimited PTO
- Holidays + Canary Days
- Birthday Holiday
- Office Exchange travel stipend
- Canary Hotel Experience credit
- Preferred Hotels Discount (minimum 30% off)
- Self Improvement Club monthly budget
- Professional Development learning stipend
- Referral Program cash bonus
About the Company
- 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.
- Partnered with renowned hospitality brands like Marriott International, Four Seasons, and Wyndham Hotels & Resorts to increase revenue, improve operations, and elevate the guest experience.
- Executed the largest deployment of autonomous AI systems in hospitality.
- One of the top-funded hotel technology companies, having raised nearly $200M.
- 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.
- Values rigor and velocity: high standards, fast pace, real ownership.
- Seeking passionate individuals who want to grow with the company and take on responsibility.
Equal Opportunity
- 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.