Director, Technical Support
Remote · Canada
Job Summary
Director of Technical Support to lead Ada’s global 24/7 two-tiered Technical Support organization (Tier I Advisors and Tier II Engineers). Own end-to-end technical support governance, tooling strategy, and team development; act as strategic partner to Engineering, Product, and Customer Solutions. Build AI-powered workflows, define and optimize AI adoption targets, and drive continuous improvement in AI-enabled support operations. Serve as the executive escalation point for high-severity client issues, align with Engineering/Product on product strategy, and ensure backlog hygiene and effective queue management. Leverage Ada’s AI platform (Claude and MCP integrations) to automate workflows, improve team productivity, and differentiate Ada in the enterprise market. Represent Technical Support in leadership discussions, translate client feedback into structured bug reports, and drive measurable outcomes in AI-assisted ticket resolution, deflection, and time-to-resolution. Notable skills include RESTful APIs troubleshooting, cloud services, OAuth 2.0/JWT, Postman, Swagger, Datadog, log analysis, LLM-based tooling, AI workflows, and cross-functional leadership.
Required Qualifications
- Experience in technical support or customer-facing technical roles with senior leadership capacity
- Proven track record building and scaling technical support in high-growth B2B SaaS/CX/AI-native environments
- Deep expertise troubleshooting RESTful APIs, cloud-based services, middleware, modern authentication mechanisms (OAuth 2.0, JWT)
- Hands-on experience with LLM-based tooling, prompt engineering, AI agent workflows, and MCP integrations
- Ability to translate client feedback into actionable bug reports and influence product strategy
- Excellent communication and leadership skills
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