Staff Cloud Engineer

Founded in 2017, Trust & Will is the leading digital estate planning platform, trusted by over one million users. We provide modern, accessible solutions to help families protect their legacies with attorney-approved, legally valid documents tailored to individual state requirements. Our seamless online platform simplifies the estate planning and settlement process, empowering individuals to create wills and trusts while also partnering with financial advisors, attorneys, and institutions to make legacy planning more inclusive and affordable. Design, build, and evolve the cloud platform that powers Trust & Will’s engineering organization. This role combines cloud architecture, infrastructure automation, platform engineering, software engineering, and AI-assisted development to improve reliability, scalability, security, and developer productivity. Staff level individual-contributor role with platform-wide influence and technical leadership expectations. About the Role: Design, build, and operate secure, scalable multi-account AWS infrastructure using Terraform and Terragrunt, driving standardization, reusable modules, and reduced configuration drift. Evolve CI/CD pipelines and deployment automation to enable faster, safer, and more reliable releases. Build self-service platforms and automation that reduce developer friction and manual operational toil. Own cloud architecture across compute, networking, IAM, secrets management, observability, and security controls while maintaining SOC2 and compliance alignment. Implement monitoring, observability, and alerting that improve operational visibility and incident readiness. Partner with software engineers to increase system reliability, scalability, and deployment safety. Drive AWS cost optimization and operational efficiency without slowing engineering velocity. Mentor engineers and raise infrastructure, security, and operational maturity across the organization. Qualifications: 8+ years building and operating production AWS systems in multi-account environments. Strong expertise with Terraform and multi-account / multi-environment IaC patterns at scale (Terragrunt experience strongly preferred), including reusable module design and environment management. Strong software engineering background with production experience building applications, services, APIs, automation frameworks, and tooling; demonstrated ability to write maintainable, production-quality code. Strong experience with modern CI/CD systems and automated deployment pipelines (GitHub Actions preferred). Experience supporting production databases (MySQL, PostgreSQL, MongoDB) and observability platforms (Datadog, OpenTelemetry, CloudWatch, or equivalent). Strong scripting and automation skills in Python, TypeScript, Bash, or similar. Experience supporting SOC2, audits, and compliance in regulated environments. Demonstrated technical leadership through ownership of significant infrastructure or platform initiatives and driving measurable operational improvements across engineering teams. Ability to influence standards, mentor engineers, and elevate team maturity through clear communication and execution-focused ownership.AI-First Requirements (Non-Negotiable) Actively uses AI-assisted development tools (Claude Code, Cursor, GitHub Copilot, or similar) as a core part of daily workflows for infrastructure, automation, debugging, and productivity. Demonstrated ability to safely evaluate, validate, and operationalize AI-generated solutions in production environments. Experience with AI-enabled operational workflows and familiarity with LLM platforms such as Amazon Bedrock. Candidates must demonstrate practical AI-native engineering approaches during the interview process. This position is available to candidates residing in the following states only: California (CA), Colorado (CO), Florida (FL), Georgia (GA), Idaho (ID), Illinois (IL), Maryland (MD), New Jersey (NJ), New York (NY), North Carolina (NC), Pennsylvania (PA), T…