Senior Technical Program Manager, Services Tools & Diagnostics

Responsibilities

• Architect and build systems that encode how GCS operates, including account health observability, intelligent routing, knowledge retrieval, and workflow automation across TAM, PS, and EM motions, with cost optimization.
• Build AI workflows using the Anthropic Claude API, Claude Agent SDK, and Claude Code, including MCP servers that connect agents to Slack, Jira, Zendesk, Grafana, Airtable, and internal Twilio systems.
• Partner with CXO to design decision frameworks for autonomous system actions versus human-in-the-loop, owning guardrails to prevent failures such as edge cases, prompt injection, and unintended behaviors.
• Extend observability and analytics with production-quality dashboards and integrations across Grafana (ClickHouse-backed), Salesforce, Tableau, Looker, and Airtable, selecting the right tool for the audience and data source.
• Operate within and mature CXO's vetting-and-graduation governance model, including versioning, evaluation frameworks, A/B testing, and performance measurement focused on GCS.
• Instrument all built systems for metrics like retrieval accuracy, action success rates, deflection, and failure patterns; tie technical performance to GCS business outcomes such as 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.

Qualifications

Required:

• 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 (OAuth 2.0, API keys, token refresh, webhooks, pagination, rate limiting, error handling, retries, JSON transformation).
• Hands-on experience building AI systems with large language models, including tool use/function calling, structured outputs, prompt architecture, evaluation harnesses, and deploying MCP servers to connect enterprise systems.
• Deep understanding of how LLMs reason, 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/dashboards), Tableau (data modeling, calculated fields, LOD expressions, publishing), Looker (LookML modeling, Explores, derived tables, dashboards), and Airtable (base/table design, automations, scripting, API integration), with judgment to select the right tool.
• Strong engineering practices: Git-based version control, code review, basic CI, and least-privilege patterns for customer data.
• Ability to translate business requirements into system specifications and explain complex technical behavior to non-technical stakeholders.

Desired:

• Experience embedded in a support or professional services organization, building systems for those teams.
• 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.