Senior Technical Program Manager, Services Tools & Diagnostics

Join the team as our next Senior Technical Program Manager, Service Delivery Systems on the Global Customer Services (GCS) Strategy & Operations team. This role owns the technical foundation that powers how GCS delivers customer outcomes at scale — the intelligent automation, knowledge systems, and decision logic embedded in the service delivery workflows of our Technical Account Management, Professional Services, and Engagement Management teams. You'll design and build systems, including AI workflows that operate within the Customer Experience Operations (CXO) governance model and you'll be accountable to GCS business outcomes: resolution rates, revenue-per-headcount, product adoption and more. This role sits at the intersection of engineering and program management. You'll write code every week, but your success is measured in GCS outcomes for customers, not a technology roadmap.

• Architect and build the systems that encode how GCS operates — account health observability, intelligent routing, knowledge retrieval, and workflow automation across our TAM, PS, and EM motions; including cost optimization.
• Build AI workflows using the Anthropic Claude API, Claude Agent SDK, and Claude Code, including MCP (Model Context Protocol) servers that connect agents to Slack, Jira, Zendesk, Grafana, Airtable, and internal Twilio systems.
• Partner with CXO to design the decision frameworks that determine when systems act autonomously, when humans stay in the loop and own the guardrails — edge cases caught, prompt injection blocked, unintended behaviors prevented — that keep failure rates low.
• Extend GCS's observability and analytics foundation with production-quality dashboards and integrations across Grafana (ClickHouse-backed), Salesforce, Tableau, Looker, and Airtable — choosing the right tool for the audience and data source rather than defaulting to one platform.
• Operate within CXO's vetting-and-graduation governance model, and help mature it: versioning, evaluation frameworks, A/B testing, and systematic performance measurement across scenarios with GCS specific focus.
• Instrument everything you build — retrieval accuracy, action success rates, deflection, and failure patterns — and tie technical performance to GCS outcomes like time to value, resolution rate, cost-per-ticket, and time-to-resolution.
• Translate complex system behavior into plain language for director and executive audiences while producing clear technical documentation for the teams who depend on your systems.

• 7+ years of experience building production software or technical systems, in roles such as platform engineering, solutions architecture, or hands-on technical program management.
• Production-quality proficiency in Python and/or TypeScript (Node.js), with fluency in REST API integration fundamentals: authentication (OAuth 2.0, API keys, token refresh), webhooks, pagination, rate limiting, error handling and retries, and JSON transformation.
• Hands-on experience building AI systems with large language models — tool use / function calling, structured outputs, prompt architecture, and evaluation harnesses — including building and deploying MCP servers to connect enterprise systems.
• Deep understanding of how large language models work: how they reason, where they fail, and why.
• Fluency in RAG architectures, prompt engineering patterns, and agent frameworks.
• Advanced SQL, including analytical queries against columnar stores such as ClickHouse.
• Dashboard and application development experience across Grafana (data sources, panels, variables, dashboard-as-code, alerting), Salesforce (SOQL, report types, Lightning reports and dashboards), Tableau (data modeling, calculated fields, LOD expressions, publishing to Tableau Cloud or Server), Looker (LookML modeling, Explores, derived tables, publishing to dashboards), and Airtable (base/table design, automations, scripting extensions, API integration) — with the judgment to choose the right tool for a given audience and data source.
• Strong engineering practices: Git-based version control, code review, basic CI, and least-privilege patterns when handling customer data.
• Demonstrated ability to translate business requirements into system specifications and explain complex technical behavior to non-technical stakeholders.

• Experience embedded in a support or professional services organization, building systems for the teams doing the work.
• Experience with Zendesk or similar service platforms, including APIs, triggers, and routing logic.
• Experience defining metrics and observability for AI systems in production, and running structured A/B tests or evaluations.
• Familiarity with Twilio's products or the CPaaS/SaaS domain.

This role will be remote, but is not eligible to be hired in San Francisco, CA, Oakland, CA, San Jose, CA, or the surrounding areas.