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), Texas (TX), Vermont (VT), Nevada (NV), Utah (UT)

Bonus Points for:

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.

What Success Looks Like:

Increased infrastructure automation and reduced manual operational toil.

Faster, safer, more reliable deployments with improved consistency and lower configuration drift.

Stronger operational visibility, observability, and incident readiness.

Reduced developer friction and higher engineering velocity.

Improved infrastructure maturity, security posture, compliance alignment, and AWS cost efficiency.

Widespread, safe adoption of AI-assisted engineering practices that accelerate delivery.

Full-time Employee Benefits & Perks:

Compensation: Salary + Equity

Our salary range for this position is $198,000 - $210,000, in addition to compensation we also include an employee equity package as a component of our offer along with other benefits and perks outlined below. 

PTO

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

Health and Wellness Benefits

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)

Extra

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 

About Trust & Will: 

We are a remote-first company, giving our employees the flexibility they need to work in an environment that best suits their needs. Our hiring process is also conducted virtually unless otherwise noted. We are a company that was founded in San Diego, CA, and offer a collaborative co-working space that is available for you to use if you'd like but not required. #LI-Remote

We are proud to be a certified B Corporation, using business as a force for good. We are committed to building a healthy, sustainable, and engaging working environment for all employees, their families, and communities. We publish an annual impact report to outline our positive contributions to our world and set an example for all employers.

Trust & Will's mission is to help every family leave their legacy through affordable, accessible estate planning. That starts with the people we hire and the ways in which we support the development of their unique talents and capabilities. We are committed to prioritizing ways to make our company and industry more inclusive. This means we must be revolutionary in the way we value diversity to revolutionize our business sector. At Trust & Will, everyone has a seat at the table and space to be their authentic selves because only in a company that is inclusive and diverse can we truly stand in our members' shoes.

California Privacy Notice: Trust & Will collects personal information from applicants including identifiers, professional/employment history, and education information to evaluate qualifications and communicate about your application. California residents have the right to know what information we collect, request a copy, correct inaccuracies, or request deletion (subject to exceptions). To exercise these rights, contact legal@trustandwill.com. For more information, visit our privacy policy .

Trust & Will may use AI tools to assist with administrative recruiting tasks. All final hiring decisions are made by people. For accommodations, contact people-ops@trustandwill.com .

This position will remain open until filled, but applications received by July 3, 2026 will receive priority consideration.