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