Staff Cloud Engineer
Trust & Will, founded in 2017, is a leading digital estate planning platform that has assisted over one million users in creating attorney-approved, legally valid documents tailored to individual state requirements. The company aims to simplify the estate planning and settlement process, empowering individuals to create wills and trusts while partnering with financial advisors, attorneys, and institutions to make legacy planning more inclusive and affordable.
The Staff Cloud Engineer will 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. As a staff-level individual contributor, the position carries platform-wide influence and technical leadership expectations.
Key responsibilities include designing and operating secure, scalable multi-account AWS infrastructure using Terraform and Terragrunt, evolving CI/CD pipelines and deployment automation, building self-service platforms and automation to reduce developer friction, and owning cloud architecture across compute, networking, IAM, secrets management, observability, and security controls while maintaining SOC2 and compliance alignment. The role also involves implementing monitoring, observability, and alerting to improve operational visibility and incident readiness, partnering with software engineers to increase system reliability, scalability, and deployment safety, driving AWS cost optimization and operational efficiency, and mentoring engineers to raise infrastructure, security, and operational maturity across the organization.
Candidates should have over 8 years of experience 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), and a strong software engineering background with production experience building applications, services, APIs, automation frameworks, and tooling. Additional requirements include 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, and experience supporting SOC2, audits, and compliance in regulated environments. Candidates must also demonstrate technical leadership through ownership of significant infrastructure or platform initiatives and driving measurable operational improvements across engineering teams, and have the ability to influence standards, mentor engineers, and elevate team maturity through clear communication and execution-focused ownership.
The compensation package includes a salary range of $198,000 - $210,000, in addition to an employee equity package. Benefits encompass flexible time off, generous paid company holidays, monthly friends & family days, paid time off to volunteer in the community, exceptional health benefits (medical, dental, vision, life, and disability insurance), mental health support, financial wellness benefits, flexible work schedules, a family-friendly work environment, learning & development reimbursement, optional company-sponsored events and travel, and a $500 work-from-home stipend with Apple accessories.
Trust & Will is a remote-first company, offering employees the flexibility to work in an environment that best suits their needs. The company is a certified B Corporation, committed to building a healthy, sustainable, and engaging working environment for all employees, their families, and communities. Trust & Will's mission is to help every family leave their legacy through affordable, accessible estate planning, and they prioritize inclusivity and diversity in their hiring practices.