Trust & Will

Compensation

Full Description

About You: You are a cloud-first engineer who thrives at the intersection of infrastructure, software architecture, and DevOps/DevSecOps excellence. You care deeply about developer productivity, system reliability, secure systems, and elegant infrastructure design that scales with business needs. You are energized by horizontal work - enabling other teams through shared infrastructure, CI/CD platforms, and automated operations. You are a pragmatic problem-solver who thrives on making real-world tradeoffs between scale, simplicity, cost, and resilience. You proactively engage across teams, mentoring engineers and influencing architecture with a bias for action, experimentation, and learning. You believe that security, scalability, and observability are not optional and that DevSecOps is a team sport - you empower developers to build secure systems through well-designed guardrails, tooling, and education. You hold a strong belief that AI is an enabler to higher productivity and efficiency through regular practice and challenging of long held positions and beliefs. About the Role: Technical Leadership & Impact Serve as the center of excellence for cloud infrastructure, DevOps, and DevSecOps practices, helping embed security and resilience into every stage of the software lifecycle. Architect, evolve, and harden our cloud platform to ensure it is secure, scalable, observable, and self-healing by design. Build and maintain foundational cloud tooling, deployment pipelines, and platform services that empower vertical squads to ship quickly and safely. Champion a pragmatic approach to architecture, balancing elegant monoliths with serverless augmentation and microservice boundaries where appropriate. Lead platform-wide initiatives around resilience engineering, incident response readiness, and developer enablement infrastructure. Influence technical direction by identifying opportunities to integrate AI into development processes, driving efficiency and fostering innovation across engineering teams. Quality & Impact Design and implement CI/CD pipelines, testing strategies, and ephemeral environments that accelerate delivery while safeguarding reliability. Own the strategy and implementation of monitoring, alerting, and logging—driving observability as a cultural and technical standard. Evaluate and implement automated testing of infrastructure reliability, scalability, and fault tolerance. Drive build vs buy decisions, evaluating tradeoffs in operational burden, cost, and strategic value. Proactively identify scaling bottlenecks and architectural risks, then lead efforts to resolve them across services and teams. Collaboration, Innovation & Mentorship Drop into squads as needed to unblock delivery, ensure architectural alignment, or accelerate delivery of cloud-critical initiatives. Partner with security, compliance, product, and engineering leadership to ensure platform integrity and operational excellence. Mentor and support engineers across the org in cloud architecture, infra-as-code, performance optimization, and scalable design patterns. Stay abreast of emerging cloud technologies, evaluating industry trends and applying them to real-world business outcomes—not theoretical ones. Foster a culture of resilience, efficiency, and empowerment, modeling thoughtful decision-making in ambiguous and high-stakes environments. Approach AI with a strategic, enterprise-wide mindset, shaping technical vision, defining architectural patterns, and influencing cross-functional roadmaps to integrate AI seamlessly into cloud ecosystems to drive transformative business outcomes. Qualifications Core Experience 7+ years of software engineering experience, with significant time in cloud-native systems design, DevOps tooling, and infrastructure automation. Deep expertise in designing, building, and maintaining systems on AWS (preferred), GCP, or Azure. Proven experience with Infrastructure-as-Code using Terraform, AWS CDK, or similar tooling. Track record of architecting secure, observable, and cost-effective platforms that serve as internal products for other engineers. Experience implementing and scaling CI/CD pipelines, including build pipelines, test orchestration, environment management, and rollbacks. Deep understanding of platform security, identity & access management (IAM), secrets management, and threat modeling in a cloud environment. 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) Skills & Tools Languages: Python, Go, TypeScript/Node.js, Bash Cloud Platforms: AWS (strongly preferred), with deep understanding of the critical products across the ecosystem (EC2, ECS, Lambda, API Gateway, RDS, S3, CloudWatch, IAM, SecurityHub, etc.) IaC & Deployment: Terraform, CloudFormation/CDK, GitHub Actions, ArgoCD, CircleCI Observability: Datadog, OpenTelemetry, Prometheus/Grafana, Sentry, ELK Containerization: Docker, Kubernetes, ECS, Fargate Testing: Integration testing of infrastructure, ephemeral environments, chaos testing, load testing Security: Secure-by-design principles, SOC2/GDPR/HIPAA/CCPA compliance support, zero-trust architecture Bonus Points for: Experience working in a tech company and/or high-growth startup Familiarity with Agile development methodologies and tools (Scrum/Kanban, JIRA) Experience with paired programming Experience integrating AI-assisted workflows effectively into complex software engineering tasks. Employee Benefits & Perks: Compensation: Salary + Equity Our salary range for this position is $187k - $215k, 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 Fantastic health benefits including medical, dental, vision, life insurance, and generous parental leave Financial wellness benefits (Equity & tax advisory support, financial coach support, and employer-sponsored 401k with an employer match) Guest speakers & reimbursement for learning opportunities Extra Flexible work schedule + hours Family-friendly work environment. We support the complexity of a remote world with the needs of families 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.