We are seeking a Senior Technical Support Specialist with a core focus on software integration and delivery. In this role, your primary mission will be to own the technical setup, configuration, and data mapping required to integrate Top Hat with our institutions. You will ensure seamless software connectivity while supporting broader sales and advanced technical support initiatives.

You Will:

• Partner with institutional IT teams to gather requirements, scope integration pathways, and map data fields between Top Hat and Learning Management Systems

• Lead the technical setup and configuration of integrations for school partners, ensuring successful implementation

• Troubleshoot and resolve system-level integration errors (e.g., authentication failures, API timeouts, data sync mismatches)

• Act as the primary subject matter expert to resolve complex integration issues and answer technical inquiries from school administrators

• Monitor, troubleshoot, and escalate technical issues to ensure a seamless classroom experience for our users

• Own the refinement of documentation and best practices for integrations

• Analyze technical trends and customer feedback to provide insights and recommendations to Product Development, contributing to informed decision-making at both tactical and strategic levels

• Support Sales Reps with active deals by joining customer calls as the SME and answering technical support-related questions

• Provide technical support during peak periods by directly handling complex cases, critical system issues, and high-priority user requests, ensuring rapid resolution while maintaining service reliability and operational standards

Requirements:

• 2+ years of experience in a Technical Support or Solutions Engineering role, preferably in a technology-related industry

• Practical experience working with APIs, JSON, HTTP protocols, and database queries (SQL)

• Solid understanding of data exchange and authentication protocols (e.g., SSO, SAML, OAuth)

• Hands-on experience with EdTech data integrations (LTI standards, Canvas, Blackboard, or Brightspace APIs) is highly preferred

• Strong technical background with experience working closely with Product Managers or Engineers

• Demonstrated ability to manage high-volume technical support operations, with a focus on proactive problem-solving and customer satisfaction

• Excellent analytical skills with the ability to interpret data and drive informed decision-making

Why team members love working at Top Hat:

• A noble mission that creates meaningful, fulfilling work

• A team that cares deeply for customers and for each other

• Flexible, remote first work environment

• Professional learning and development for all role levels

• An awesome and welcoming Toronto HQ

• Competitive health benefits that start on day one

• A management team focused on performance, growth, engagement and connection

• Our winning strategy and market potential

• Innovative PTO policy with lots of time and space for self-care

• Passionate customers that believe in us—and what we do

• A chance to work with new tech like generative AI—and see the customer impact