Staff Cloud Engineer

Trust & Will

1d • $198,000 - $210,000 • Remote

About The Position

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.

Requirements

• 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.
• 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.

Nice To Haves

• 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.

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.

Benefits

• Salary + Equity
• PTO
• Flexible time off
• Generous paid company holidays and breaks
• Monthly friends & family day
• Paid time off to volunteer
• Exceptional health benefits including medical, dental, vision, life, and disability insurance
• 100% of premiums covered for employees and dependents on medical coverage
• Mental health support through Spring Health
• Access to One Medical for primary care
• Access to Cleo for family planning and caregiving
• Financial wellness benefits
• Unlimited 1:1 sessions with a UBS financial coach
• Employer-sponsored 401k with up to 4% company match
• Flexible work schedule + hours
• Family-friendly work environment
• Up to $1,000 annually in learning & development reimbursement
• $500 Work from home stipend
• Apple accessories

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed