Sr. Manager, Customer Support (Hybrid - Toronto) or (Remote - US)

About the role

The Senior Manager, Customer Support will lead, mentor, and scale a high-performing technical support team, overseeing daily operations, managing ticket queues, escalations, and ensuring adherence to established Service Level Agreements (SLAs) and quality standards. This role requires deep expertise in Zendesk administration and optimization, as well as the ability to diagnose and resolve complex technical issues collaboratively with engineering and product teams.

Responsibilities

• Lead, mentor, and scale a high-performing technical support team, fostering a culture of accountability, continuous learning, and customer empathy.
• Oversee daily support operations, managing ticket queues, escalations, and ensuring adherence to established SLAs and quality standards.
• Administer and optimize our Zendesk instance, including triggers, automations, macros, and reporting dashboards to drive operational efficiency.
• Act as the primary escalation point for complex technical issues, collaborating closely with Engineering and Product teams to diagnose, track, and resolve software bugs.
• Analyze support metrics and KPIs (including but not limited to TTR, FTR, Deflection Rate, CSAT) to identify trends, pinpointing product friction points or training gaps to improve the overall customer experience.
• Develop and maintain internal documentation, knowledge base articles, and standard operating procedures for the technical support team.
• Implement AI tooling and automation throughout the Support organization.

Requirements

• SaaS Experience: 5+ years of experience working in technical support, specifically within a B2B SaaS environment.
• Leadership: 3+ years of experience successfully managing, leading, or mentoring a technical support or customer-facing team.
• Tooling Expertise: Deep, hands-on experience using and administering Zendesk (ticketing, reporting, and workflows) or similar tools.
• Domain Knowledge (Preferred): Experience working within a financial technology (FinTech) SaaS company OR a post-secondary degree/background in Finance or Accounting.
• Experience managing leaders & individual contributors.
• Technical Aptitude: Strong troubleshooting and analytical skills, with the ability to translate complex technical jargon into clear, actionable steps for non-technical users.
• Experience implementing AI tooling & automation throughout a Support organization.

Critical Skills/Experience

• Self-motivated, self-starter with a zeal to win.
• Great communicator; strong oral and written skills.
• Able to think creatively and innovatively.
• Hands-on problem solver who enjoys cracking difficult nuts.
• Quick study – able to pick up and apply new concepts in a hurry.
• Track record of achievement.
• Enjoys working on and helping to build outstanding teams.
• Demonstrates an entrepreneurial spirit and gets stuff done.
• A sense of humor and don’t take themselves too seriously.

Benefits

• Competitive Salary
• Quality Medical, Dental, and Vision Insurance Plans
• Short and Long Term Disability Insurance
• Life Insurance
• 401K Plan with Match
• Flexible Personal Time Off Policy
• Company-Paid Holidays Observed
• Annual Holiday “Dimming of the Lights” (aka: reduced work hours)
• Parental Leave