Director of Engineering - Core Platform & Tooling

Join Our Mission to Revolutionize Healthcare

Thoughtful is pioneering a new approach to automation for all healthcare providers! Our AI-powered Revenue Cycle Automation platform enables the healthcare industry to automate and improve its core business operations.

We're looking for an Exceptional Direct of Engineering for our Core Platform and Tooling team.

As the Director of Core Platform and Tooling at Thoughtful AI, you’ll lead the engineering function responsible for building and scaling the infrastructure backbone that powers our AI Agents across the healthcare ecosystem. This is a critical leadership role focused on designing a secure, reliable, and high-velocity platform to support the next phase of our growth.

You will own the vision and execution for our compute, observability, messaging, and internal tooling layers, ensuring we can scale confidently as demand increases. Your team will enable product velocity and platform stability, delivering infrastructure that supports our engineers and systems as we grow from today’s workloads to tomorrow’s ambitions.

This is an ideal role for a hands-on engineering leader who has operated modern cloud platforms in production, scaled teams and systems, and thrives in regulated, high-growth environments.

Learn more about our Warrior culture.

Key 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.

What Success Looks Like

• A high-performing team with clear ownership, strong technical depth, and platform accountability.
• A scalable, reliable platform that supports growing product complexity and engineering throughput.
• Engineers move faster and safer thanks to high-quality tooling, automation, and platform abstractions.
• Platform infrastructure meets or exceeds targets for reliability, performance, and compliance.
• Infrastructure is a strategic enabler, not a bottleneck.

Minimum Qualifications

• 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.

Bonus Points

• 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.

Why Thoughtful?

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