Director of Engineering - Core Platform & Tooling

Summary

Join Thoughtful's mission to revolutionize healthcare by leading their Core Platform and Tooling engineering team. As Director, you will build and scale the infrastructure powering their AI-powered Revenue Cycle Automation platform. This critical leadership role involves defining the vision and execution for compute, observability, messaging, and internal tooling. You will manage a team of 12+ senior engineers, ensuring platform stability and scalability while adhering to regulatory standards (SOC 2 Type II, HIPAA). Success hinges on building a high-performing team, creating a reliable platform, and accelerating engineering productivity. The ideal candidate is a hands-on leader with extensive experience in cloud platforms, scaling teams and systems, and navigating regulated environments.

Requirements

• 10+ years of experience in software or infrastructure engineering, with 4+ years in technical leadership roles
• Proven success running a scaled-out platform
• Deep experience with Kubernetes (EKS) and the broader AWS ecosystem
• Familiarity with Kafka or managed messaging systems in real-world production use
• Proven success managing high-talent engineering teams, including Senior and Staff ICs
• Hands-on experience with infrastructure in regulated environments (e.g., SOC 2 Type II, HIPAA)
• Excellent written and verbal communication skills, with the ability to drive clarity, alignment, and execution
• Strong architectural judgment and ability to scale systems pragmatically

Responsibilities

• Lead the Core Platform and Tooling team, with the expectation of growing the existing team to 12+ Senior and Staff-level ICs across infrastructure and internal tooling
• Define and drive the core platform vision, architecture, and roadmap, ensuring it meets evolving scale, performance, and security needs
• Own and evolve our Kubernetes platform (EKS) to support highly available and efficient service deployment
• Manage messaging infrastructure (including AWS Managed Kafka) to support real-time, event-driven workflows
• Improve CI/CD pipelines, observability, and internal tooling to accelerate engineering productivity
• Ensure our infrastructure complies with SOC 2 Type II, HIPAA, and other regulatory standards
• Collaborate cross-functionally with Product, Engineering, and Security leadership to align infrastructure capabilities with business needs
• Build and operationalize clear metrics, SLOs, and reliability practices across core platform systems

Preferred Qualifications

• Experience building Developer Experience (DevEx) platforms and internal tooling
• Familiarity with Knative and serverless event-driven patterns on Kubernetes
• Exposure to data lakehouse tooling (e.g., Athena, Glue, Parquet) or distributed analytical systems
• Experience supporting or evolving orchestration frameworks like Robocorp or Temporal

Benefits

• Competitive compensation
• Equity participation: Employee Stock Options
• Health benefits: Comprehensive medical, dental, and vision insurance
• Time off: Generous leave policies and paid company holidays