Senior Technical Support Agent

Canary Technologies Corp•Dallas, NY

About The Position

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.

Requirements

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.

Nice To Haves

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).

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.
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.
Show up and demonstrate integrity, reliability, adaptability, collaboration, and ownership of your work everyday.

Benefits

Unlimited PTO
Holidays + Canary Days
Birthday Holiday
Travel stipend to visit the team in person at our SF, NY, or Dallas hubs.
Credit toward stay at a Canary hotel.
Preferred Hotels Discount: Enjoy a minimum 30% off the best available rate at select partner hotels globally.
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.
Stock option grant, subject to board approval.