Senior Technical Support Agent

Senior Technical Customer Support AgentSenior 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.What You'll DoProduct & 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.What We're Looking For3+ 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).CompensationTarget 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.Perks & BenefitsWe work hard to make Canary a fun, rewarding, and high-energy place to work. Here's how we take care of our flock:Time OffUnlimited 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 FlexibilityOffice 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 & CommunitySelf 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.