Note: The job is a remote job and is open to candidates in USA. The Planet Group is focused on building innovative AI systems that automate manual tasks across various departments. They are seeking a Senior Director for AI Automation who will lead engineering sprints and drive the development of multi-agent systems, combining hands-on coding with strategic leadership.

Responsibilities

• Own end-to-end department sprints (e.g., an HR sprint delivering resume screening, OKR coaching, performance ratings, milestone email automation in 4 weeks)
• Run discovery sessions with department leaders, map workflows, and translate them into concrete AI automation plans
• Design and ship Python/FastAPI backends integrating with HRIS, ERP, CRM, finance, and project management systems
• Build secure Next.js/React frontends with Okta SSO, RBAC, audit trails, and Playwright test coverage
• Architect and operate multi-agent systems (coordination, handoffs, feedback loops) using LLM APIs (Anthropic Claude via AWS Bedrock, OpenAI, etc.)
• Navigate enterprise security (OAuth2, Zscaler proxies, SSL certs, Kubernetes networking, JWKS verification)
• Deploy via GitLab CI/CD to AWS EKS (Kubernetes, ArgoCD, Helm, Secrets Manager) – shipping multiple times per day
• Build reusable automation recipes and teach non-engineers how to extend them (“leave it improvable” principle)

Skills

• 10+ years building production software end-to-end (backend, frontend, integrations, infrastructure)
• Significant leadership scope (former CTO, VP Engineering, or equivalent ownership) while still writing code daily
• Shipped SaaS products with OAuth2, multi-tenancy, audit trails, and enterprise compliance
• Deep AI/ML engineering experience with production LLM systems (OpenAI, Anthropic, AWS Bedrock) and agent frameworks
• Production Python (FastAPI, Pydantic, httpx, pytest) and TypeScript/React (Next.js App Router, server components)
• AWS + Kubernetes (EKS operations, GitLab CI/CD, ArgoCD, Helm, Secrets Manager)
• Enterprise security experience (Zscaler, SSL, Kubernetes networking, JWKS, HIPAA/SOC 2 or similar)
• Active, daily use of AI engineering tools (GitHub Copilot, Cursor, Windsurf, Cline, or similar). Hard requirement
• At least one automation you've built that eliminated significant manual work and is still in use in production
• Strong communication: can run discovery with executives, explain security trade-offs, and write crisp architecture docs
• Led engineering teams of 5–20 people (hiring, mentoring, performance decisions)
• Experience building agentic systems: agent coordination, scheduled routines, feedback loops
• MCP (Model Context Protocol) experience, custom connectors into enterprise systems
• Healthcare or regulated-industry background (HIPAA, SOC 2, or similar)
• Active contributor to AI/ML communities (open source, talks, papers)

Benefits

• Comprehensive health insurance (medical, dental, vision).
• 401(k) with company match and vesting.
• HSA contribution, disability, AD&D, life insurance.
• Generous PTO, paid holidays, parental leave.
• Remote-first environment, home office stipend, conference support.
• Annual continuing education budget and access to AI tooling.

Company Overview