Senior Security Engineer

Summary

Join Thoughtful's mission to revolutionize healthcare with their AI-powered Revenue Cycle Automation platform. As a Senior Security Engineer, you will be responsible for securing and scaling their technology stack, owning platform security, system reliability, audit readiness, and integration strategy across cloud and hybrid environments. You will lead foundational work in infrastructure hardening, audit controls, and production observability, directly supporting mission-critical AI agents. You will have executive support and budget to modernize their infrastructure. The role requires a strong track record of leading integrations, hardening infrastructure, and ensuring audit/compliance readiness. Thoughtful offers competitive compensation, equity participation, comprehensive health benefits, generous leave policies, and paid company holidays.

Requirements

• 8+ years of experience spanning Security, DevOps, and/or SRE roles in high-availability, cloud and hybrid environments—with a strong track record of leading integrations, hardening infrastructure, and ensuring audit/compliance readiness
• Start-up mentality - desire to tackle ambiguous scope of work and willing to do whatever is necessary to drive the company/mission forward
• Track record leading complex infrastructure integrations
• Deep AWS expertise; strong experience with Azure and/or GCP a bonus
• Proficiency in OpenTofu or Terraform for Infrastructure-as-Code
• Comfortable navigating hybrid cloud environments (e.g. EKS, legacy VMs, VPN tunnels)
• Solid Kubernetes experience (Knative experience a plus)
• Strong networking fundamentals and experience with on-prem systems
• Familiar with incident tooling (PagerDuty, Opsgenie) and setting SLOs/SLAs
• Personable and cross-functional: able to build rapport with stakeholders across engineering, compliance, and executive leadership
• Security-first mindset, with an eye for compliance and audit readiness
• Proficiency in SOC2 Type 2, HITRUST preparation
• Comfortable spinning up new infrastructure as needed

Responsibilities

• Lead infrastructure and tooling decisions as we unify multiple environments into a single, scalable platform
• Own and drive SOC 2 Type II and HITRUST prep, working across engineering, compliance, and security
• Ensure uptime, scalability, and fault tolerance across services. Set and enforce SLAs
• Stand up our alerting, escalation, and incident response systems
• Improve logging, metrics, and dashboards using tools like HyperDX
• Spin up and manage production-grade infrastructure using OpenTofu/Terraform
• Architect infrastructure with security best practices, including VPNs, IPsec tunnels, and hybrid network topologies

Preferred Qualifications

• You've integrated cutting edge cloud environments with customer's legacy environments
• You’ve built platforms, not just maintained them
• You treat DevOps as a product, not just a support function
• You care about developer experience, observability, and operational excellence

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