Director, Technical Support at Ada

Canada

About Us Ada is an AI customer service company whose mission is to make customer service extraordinary for everyone. We're driven to raise a new standard of quality customer service at scale, enabling enterprise companies to deliver experiences that people love–instant, proactive, personalized, and effortless. Ada is an AI transformation platform and partner—combining strategic expertise with powerful AI agent management technology to accelerate businesses’ AI maturity to keep them ahead of the curve. With Ada, 83% of customer conversations—and counting—are effortlessly resolved through automation, giving teams more time back, companies more resources to focus on growth, and customers more life to focus on what matters most to them. Established in 2016, Ada is a Canadian company that has powered over 5.5 billion interactions for leading brands like Square, YETI, IPSY, and Monday.com, saving millions of hours of human effort. Backed with over $250M in funding from tier-one investors including Accel, Bessemer, FirstMark, Spark, and Version One Ventures, Ada is a pioneer in the management and application of AI in customer service. At Ada, we see growth as a reflection of each individual owner’s personal growth. That’s why our values are rooted in driving progress and continuous improvement. If you’re ambitious and eager to grow, Ada could be the place for you. Learn more at www.ada.cx. About the Role We're seeking an experienced Director of Technical Support to lead our global 24/7 two-tiered support organization of Technical Support Advisors (Tier I) and Technical Support Engineers (Tier II). You'll own the full technical support function from SLA governance and escalation frameworks to tooling strategy and team development, while serving as a strategic partner to Engineering, Product, and Customer Solutions. This is an opportunity for you to shape a support organization that doesn't just react to customer issues, but proactively surfaces product intelligence, drives quality improvements, and becomes a competitive differentiator for Ada in the enterprise market. Critically, you will be expected to leverage Ada's own AI platform, Claude and MCP integrations to automate workflows, improve team productivity, and set a new standard for AI-native support operations. Outcomes Champion Ada's own platform for customer support automation while owning the end-to-end technical support KPI framework, including SLA design, enforcement, and continuous optimization across all tiers, along with metrics such as CSAT, escalation rates, deflection rates, and SLA adherence. Build and maintain an escalation framework that bridges Tier I and Tier II support and connects cleanly to Engineering and Product, serving as the executive escalation point for high-severity, high-impact client issues. Build AI-powered workflows and set measurable AI adoption targets for the team; 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. Act as the strategic connector between Technical Support, Engineering, Product, and Customer Solutions, translating raw client feedback into structured, and actionable bug reports. Represent technical support at the leadership level, contributing to product strategy and roadmap prioritization as both a practitioner and a thought leader. Instill rigorous backlog hygiene and queue management practices across the support organization. Leverage observability data and AI tooling to identify systemic issues before they impact clients at scale. About You Experience in technical support or customer-facing technical roles, with recent years in a senior leadership capacity managing multi-tiered teams. Proven track record building and scaling technical support functions in high-growth B2B SaaS, CX, or AI-native environments Deep expertise troubleshooting RESTful APIs, cloud-based services, middleware, and modern authentication mechanisms (OAuth 2.0, JWT) utilizing debugging tools and practices: Postman, Swagger, Datadog, log analysis, and source code review; hands-on experience with LLM-based tooling, prompt engineering, AI agent workflows, and MCP integrations is required. You don't just understand AI tools, you use them daily. You think naturally about how to automate, augment, and scale work using AI. You have a demonstrable track record of implementing AI workflows in a support or operations context — you can point to specific tools you built or deployed, workflows you automated, and measurable outcomes you drove. Exceptional people leader with demonstrated ability to build cohesive, high-performing teams across technical disciplines. Strong cross-functional influencer; you earn the trust of Engineering and Product through technical credibility, not just organizational authority. Excellent communicator who can shift fluidly between technical depth with engineers and executive-level storytelling with senior stakeholders. You're energized by the idea of using Ada's own platform to make your team more effective, and you hold yourself to the same standard you'd set for customers. You understand enterprise client dynamics and can navigate complex organizational relationships #LI-NS1 Benefits & Perks At Ada, you’ll not only build extraordinary products but also thrive in an environment designed for your success. We prioritize your well-being, growth, and work-life balance. Here’s what we offer: Benefits Unlimited Vacation: Recharge when you need to. Comprehensive Benefits: Extended health coverage, dental, vision, travel, and life insurance. Wellness Account: Empowering you to invest in your overall well-being and lifestyle. Employee & Family Assistance Plan: Resources to support you and your loved ones. Perks Flexible Work Schedule: Balance your work and personal life. Remote-First, In-Person Friendly: Options to work from home or at our local hub. Learning & Development Budget: Invest in your long-term growth goals and skills. Work from Home Budget: Equipping you with the tools and support for a seamless remote work experience. Access to Cutting-Edge AI Tools: Work with the best AI tech stack in the industry. Hands-On with LLMs: Enhance your expertise in leveraging large language models. A Thriving Industry: Join the forefront of innovation in AI, shaping the future of technology. The above Benefits and Perks only apply to full-time, permanent employees. As part of our recruitment process, we may use AI enabled tools to support certain aspects of hiring, such as interview note-taking. All hiring decisions are made by our team. Thank you for your interest in joining us at Ada. Due to the high volume of applications, we will only contact candidates whose qualifications match closely to the requirements of the position. We appreciate the time you have invested in learning more about us.