Director – Technical Support

This is a fully remote position, open to applicants in Canada.

📋 Description

• Lead the utilization of Ada's platform for automating customer support while managing the complete technical support KPI framework, which includes designing SLAs, enforcing them, and continuously optimizing across all tiers, alongside metrics such as CSAT, escalation rates, deflection rates, and SLA adherence.

• Develop and sustain an escalation framework that effectively links Tier I and Tier II support and seamlessly connects with Engineering and Product, acting as the primary escalation point for critical, high-impact client issues.

• Create AI-driven workflows and establish measurable targets for AI adoption within the team; conduct regular evaluations and foster ongoing enhancements in the integration of AI into daily support processes, with defined success metrics such as AI-assisted ticket resolution rate, deflection rate improvements, and time-to-resolution benchmarks.

• Serve as the strategic liaison among Technical Support, Engineering, Product, and Customer Solutions, converting raw client feedback into organized and actionable bug reports.

• Represent technical support at the leadership level, influencing product strategy and roadmap prioritization as both a practitioner and thought leader.

• Enforce rigorous backlog management and queue hygiene practices throughout the support organization.

• Utilize observability data and AI tools to pinpoint systemic issues before they affect clients on a large scale.

⛳️ Requirements

• Proven experience in technical support or customer-facing technical roles, with recent years spent in a senior leadership role overseeing multi-tiered teams.

• A demonstrated history of building and scaling technical support functions in rapidly growing B2B SaaS, CX, or AI-native environments.

• In-depth expertise in troubleshooting RESTful APIs, cloud services, middleware, and modern authentication mechanisms (OAuth 2.0, JWT) using debugging tools and practices such as Postman, Swagger, Datadog, log analysis, and source code review; hands-on experience with LLM-based tools, prompt engineering, AI agent workflows, and MCP integrations is essential.

• You don't just comprehend AI tools; you leverage them daily, naturally considering ways to automate, enhance, and scale work through AI.

• You possess a verifiable record of implementing AI workflows within a support or operations context — you can specify the tools you developed or deployed, the workflows you automated, and the measurable outcomes you achieved.

• An exceptional people leader with a proven ability to cultivate cohesive, high-performing teams across various technical disciplines.

• A strong cross-functional influencer; you earn the confidence of Engineering and Product through technical credibility, rather than mere organizational authority.

• An excellent communicator capable of transitioning fluidly between technical discussions with engineers and executive-level presentations with senior stakeholders.

• You are motivated by the prospect of using Ada's platform to enhance your team's effectiveness, holding yourself to the same high standards you would set for customers.

• You have a solid understanding of enterprise client dynamics and can successfully navigate complex organizational relationships.

🏝️ 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.

• 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.