Senior Technical Support Agent

• 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

Benefits

• Our health insurance has you covered on day 1
• Flexible working hours
• Training and career development
• Regular team building events
• A travel stipend for when you stay at Canary hotels
• Internal promotions from within the team
• Kitchen stocked with fruit, snacks, coffee, and more
• We’re a diverse and global team

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