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Sr. Support Engineer

Kitchener, Canada

About Dialpad
Dialpad is the leading AI-powered customer communications platform, transforming how businesses communicate with their customers. More than 50,000 companies around the globe — including Netflix, RE/MAX, Uber, Randstad, and Tractor Supply — rely on Dialpad to build stronger customer connections using real-time, AI-driven insights. Visit dialpad.com to learn more.

Being a Dialer
At Dialpad, you’ll be part of a collaborative team working toward our shared mission of making our customers and their employees wildly successful. We believe that every conversation matters, and we're elevating each one with a platform that drives real-time insights and automation for our customers.

We thrive on continuous evolution, where every employee leverages industry-leading AI to constantly refine our platform and our own skills. We seek individuals who not only meet our high standards but go beyond them. Our ambition is significant, and achieving it requires a team that operates at the highest level. We look for individuals who are not just ambitious but who also possess the traits that are fundamental to our success: Scrappy, Curious, Optimistic, Persistent, and Empathetic.

Your role
As an AI Optimization Support Engineer, you are the technical bridge between cutting-edge AI deployments and long-term operational excellence. You aren't just building the engine; you are the expert responsible for fine-tuning it to peak performance once it’s in the wild. You will take full ownership of escalated AI issues, acting as a "Technical Detective" for our most strategic customers when their Agentic AI workflows face complex challenges. Reporting to the Advanced Services leadership, you will navigate our internal Engineering and Product organizations to drive bugs to resolution and ensure our AI agents remain reliable, accurate, and high-impact.

What you'll do

  • Tier 3 AI Escalation Management: Act as the ultimate escalation point for complex AI issues, including hallucinations, retrieval failures, or integration breakdowns within the Agentic AI platform.
  • Engineering & Product Liaison: Partner directly with Core Engineering to identify, reproduce, and resolve platform bugs or systemic limitations discovered in production.
  • Performance Optimization: Analyze system logs, retrieval pipelines, and decision logic to improve the accuracy and efficiency of live AI Voice and Digital Agents.
  • Strategic Troubleshooting: Host live sessions with partners and customers to debug custom API integrations (MCP framework), CRM connectors, and multi-agent architectures.
  • Trend Analysis & Feedback: Identify trends in AI escalations to provide data-driven feedback that influences the product roadmap and improves the onboarding experience for future deployments.
  • Product Alignment and Influence: Capture common customer pain points, successful integration patterns, and platform limitations discovered in the field. Synthesize and deliver this critical, high-value signal directly back to our core Product and Engineering teams to influence the product roadmap and accelerate feature development.

Skills you'll bring

  • Experience: 4+ years in a high-impact, customer-facing senior technical support (Tier 3), escalation engineering, or forward-deployed role supporting complex SaaS or AI products.
  • AI/ML Fluency: Deep understanding of the modern AI stack, including LLMs, prompt engineering, vector databases, and how they behave in a production environment.
  • Problem Solver: You thrive on "tougher" bug-type issues and have a "team-first" attitude when navigating high-pressure crisis management situations.
  • Communicator: You can simplify complex technical failures into clear, actionable updates for both internal developers and non-technical customer stakeholders.
  • Tools: Proficient in Python or JS for script analysis, along with experience using ticketing and diagnostic tools like Zendesk, Jira, and packet captures.
  • You thrive in ambiguity, take full ownership of outcomes, and are driven by delivering tangible, measurable results for the customer, often working under tight timelines.
  • Contributor to a dynamic team culture, focused on high-growth industry innovation, team collaboration, customer success, and having fun!

We believe in investing in our people. Dialpad offers competitive benefits and perks, alongside a robust training program that helps you reach your full potential. We have designed our offices to be inclusive, offering a vibrant environment to cultivate collaboration and connection. Our exceptional culture, recognized repeatedly as a certified Great Place to Work, ensures every employee feels valued and empowered to contribute to our collective success.

Don’t meet every single requirement? If you’re excited about this role and you possess the fundamental traits, the drive, and strong ambition we seek, but your experience doesn’t satisfy every qualification, we encourage you to apply. 

Dialpad is an equal-opportunity employer. We are dedicated to creating a community of inclusion and an environment free from discrimination or harassment.

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