[Remote] Staff Cloud Engineer

Note: The job is a remote job and is open to candidates in USA. Trust & Will is the leading digital estate planning platform, trusted by over one million users. The Staff Cloud Engineer will design, build, and evolve the cloud platform to improve reliability, scalability, security, and developer productivity while providing technical leadership across the organization.

Responsibilities

• 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

Skills

• 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, 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
• 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
• 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
• Terragrunt experience strongly preferred
• GitHub Actions preferred
• Platform engineering or Internal Developer Platform experience, including self-service infrastructure for engineering teams
• Containerized workloads (ECS, Fargate, Docker) and data platforms (Snowflake, Redis, OpenSearch/Elasticsearch)
• Infrastructure cost optimization and FinOps practices
• Modernization of legacy deployment and infrastructure patterns toward fully automated models
• High-autonomy, remote-first engineering cultures with a track record of cross-team operational improvements

Benefits

• Employee equity package
• Flexible time off that you are encouraged to use
• Generous paid company holidays and breaks throughout the year
• Monthly friends & family day
• Paid time off to volunteer in your community
• Exceptional health benefits including medical, dental, vision, life, and disability insurance - we cover 100% of premiums for employees and dependents on medical coverage
• Mental health support through Spring Health, plus access to One Medical for primary care and Cleo for family planning and caregiving
• Financial wellness benefits (unlimited 1:1 sessions with a UBS financial coach and employer-sponsored 401k with up to 4% company match)
• Flexible work schedule + hours
• Family-friendly work environment. We support the complexity of a remote world with the needs of families
• Up to $1,000 annually in learning & development reimbursement
• Optional company-sponsored events and travel throughout the year
• $500 Work from home stipend + Apple accessories

Company Overview