Director, Technical Support - Ada, Remote Canada

AI Summary

Ada is seeking a Director, Technical Support for a remote role across Canada. This leader will oversee a global 24/7 two-tiered support organisation, focusing on enhancing customer service through strategic leadership and advanced AI tools. Key responsibilities include owning the full technical support function, from SLA governance to team development, and leveraging Ada's AI platform to automate workflows. Ideal candidates possess senior leadership experience in multi-tiered technical support within high-growth B2B SaaS or AI-native environments, coupled with deep expertise in APIs, cloud services, and LLM-based AI agent workflows.

About the Opportunity at Ada

Ada, a Canadian AI customer service company, is dedicated to making customer service extraordinary for everyone by enabling enterprise companies to deliver instant, proactive, personalized, and effortless experiences. As a pioneer in AI application for customer service, Ada has powered billions of interactions for leading brands, saving countless hours of human effort. This Director, Technical Support role offers a unique opportunity to shape a critical function within a rapidly growing AI transformation platform. You will lead a global 24/7 two-tiered support organisation, comprising Technical Support Advisors and Technical Support Engineers, from a remote base anywhere in Canada. This pivotal position involves owning the entire technical support function, encompassing SLA governance, robust escalation frameworks, strategic tooling implementation, and comprehensive team development. You will also serve as a vital strategic partner to the Engineering, Product, and Customer Solutions teams, ensuring seamless collaboration and alignment.

This is more than a reactive support role; it's an opportunity to proactively surface invaluable product intelligence, drive continuous quality improvements, and establish technical support as a significant competitive differentiator for Ada in the enterprise market. A critical aspect of this role involves leveraging Ada's own advanced AI platform, alongside Claude and MCP integrations, to innovate and automate support workflows. Your expertise will be instrumental in improving team productivity and setting a new industry standard for AI-native support operations. This position is ideal for an ambitious leader eager to contribute to Ada's growth and personal development within a company rooted in continuous improvement.

Key Responsibilities and Strategic Outcomes

As the Director, Technical Support, you will champion Ada's own platform for customer support automation, owning the end-to-end technical support KPI framework. This includes designing, enforcing, and continuously optimizing Service Level Agreements (SLAs) across all tiers, alongside monitoring crucial metrics such as Customer Satisfaction (CSAT), escalation rates, deflection rates, and SLA adherence. You will be responsible for building and maintaining a robust escalation framework that seamlessly bridges Tier I and Tier II support, connecting cleanly to Engineering and Product teams, while also serving as the executive escalation point for high-severity, high-impact client issues.

A core focus will be on building innovative AI-powered workflows and setting measurable AI adoption targets for your team. This involves running regular assessments and driving continuous improvement in how AI is embedded into daily support workflows, with defined success metrics including AI-assisted ticket resolution rate, deflection rate improvement, and time-to-resolution benchmarks. You will act as the strategic connector between Technical Support, Engineering, Product, and Customer Solutions, adeptly translating raw client feedback into structured and actionable bug reports. Furthermore, you will represent technical support at the leadership level, contributing significantly to product strategy and roadmap prioritisation as both a practitioner and a thought leader. Instilling rigorous backlog hygiene and queue management practices across the entire support organisation will be paramount, as will leveraging observability data and cutting-edge AI tooling to identify systemic issues proactively before they impact clients at scale.

What You Bring to Ada

The ideal candidate for this Director, Technical Support role will possess extensive experience in technical support or customer-facing technical roles, with a significant portion of recent years spent in a senior leadership capacity managing multi-tiered teams. You must have a proven track record of successfully building and scaling technical support functions within high-growth B2B SaaS, Customer Experience (CX), or AI-native environments. Deep expertise in troubleshooting RESTful APIs, cloud-based services, middleware, and modern authentication mechanisms such as OAuth 2.0 and JWT is essential. This expertise should be complemented by hands-on proficiency with debugging tools and practices including Postman, Swagger, Datadog, comprehensive log analysis, and source code review. Crucially, hands-on experience with Large Language Model (LLM)-based tooling, prompt engineering, AI agent workflows, and MCP integrations is a required qualification.

You are not merely familiar with AI tools; you actively use them daily and possess a natural inclination to automate, augment, and scale work using artificial intelligence. A demonstrable track record of implementing AI workflows in a support or operations context is expected, where you can point to specific tools you built or deployed, workflows you automated, and measurable positive outcomes you drove. Beyond technical prowess, you are an exceptional people leader with a proven ability to build cohesive, high-performing teams across diverse technical disciplines. You are a strong cross-functional influencer, earning the trust of Engineering and Product teams through your technical credibility, not solely organisational authority. Your communication skills are excellent, allowing you to shift fluidly between technical depth with engineers and executive-level storytelling with senior stakeholders. You are energized by the prospect of using Ada's own platform to enhance your team's effectiveness and hold yourself to the same high standards you set for customers. Finally, you possess a nuanced understanding of enterprise client dynamics and can adeptly navigate complex organisational relationships.