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Staff AI Agent Software Engineer

United States

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.

We’re looking for a Staff AI Agent SWE to pioneer and scale the foundations of our agentic capabilities. This is a horizontal role where you will serve as a center of excellence, empowering other squads through platform capabilities, reusable systems, and direct contribution on mission-critical initiatives. You’ll be at the forefront of building autonomous agents, multi-agent workflows, and the operational scaffolding to ensure they are performant, reliable, and scalable across the organization.

About You:

  • You are a technical innovator, deeply passionate about building intelligent agentic systems - from autonomous agents to multi-agent workflows.
  • You thrive in horizontal roles, enabling teams across an org through shared frameworks, infrastructure, and technical mentorship.
  • You approach challenges with rigor and creativity, bringing strategic thinking and deep hands-on skills in agent development and deployment.
  • You are deeply familiar with modern AI toolchains and cloud-first architecture patterns.
  • You have a strong product mindset, consistently connecting technical choices to user and business value.
  • You enjoy collaborating across disciplines and working with ambiguity to uncover scalable, high-impact solutions.
  • You demonstrate an exceptionally curious and flexible mindset - required to lead in a rapidly changing technical domain (AI).

About the Role:

Technical Leadership & Impact

  • Serve as the center of excellence for agentic systems - driving design, architecture, and operational maturity across our AI capabilities.
  • Build and maintain core infrastructure to enable other squads to confidently deploy autonomous, tool - using agents with safety and speed.
  • Design CICD pipelines, simulation test harnesses and end-to-end evaluations through observability for robust agent quality, delivery and iteration.
  • Architect scalable, cost-efficient, and resilient agent infrastructure that supports agnostic model use and cloud-native deployment.
  • Set technical strategy for cross-org agentic development - standardizing patterns, protocols, and interfaces to accelerate engineering velocity.

Quality & Impact

  • Write highly reliable, observable, and testable code for agentic systems, ensuring agents meet our standards of quality, safety, and robustness.
  • Champion automated evaluation and regression testing for agent behavior, hallucination risks, prompt reliability, and system-wide observability.
  • Optimize agent systems for performance, latency, and cost, driving improvements in throughput and user experience.
  • Identify technical debt, systemic risks, and bottlenecks in the agentic stack - and lead remediation efforts.

Collaboration, Innovation & Mentorship

  • Drop into vertical teams as an agentic expert to drive delivery of high-priority initiatives and unblock engineering squads.
  • Partner with product, design, data, and compliance teams to deliver trustworthy, impactful AI-powered features.
  • Mentor engineers across squads in agent design, evaluation, and architecture; contribute to a culture of technical learning and experimentation.
  • Evaluate and experiment with emerging trends in LLMs, agent orchestration, evaluation methods, and safety tools - bringing innovation into production practice.
  • Mentoring others through the transition to non-deterministic software development approaches to enabling agents to operate with autonomy.
  • Demonstrate effective ways of filling a context window with just the right information before the next inference step
  • Experience fine-tuning existing models to optimize for specialized outcomes

Qualifications:

Core Experience

  • 7+ years software engineering experience with exposure to large-scale distributed systems, AI/ML applications, or production-grade platform engineering.
  • Deep experience with autonomous agents, LLM orchestration, or multi-agent systems.
  • Fluency in backend languages such as Python, Node.js, or Go.
  • Production experience implementing agentic systems using custom or open source frameworks and MCP for tools.
  • Strong skills in cloud-native development on AWS/GCP, with infrastructure-as-code (CDK, Terraform).
  • Hands-on experience with CICD, observability tooling, and automated evaluation for ML/LLM pipelines.
  • 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), South Carolina (SC), Pennsylvania (PA), Texas (TX), Vermont (VT)

Skills & Tools

  • Agent Ecosystem: LangChain, OpenAI, Anthropic, Hugging Face, custom orchestrators
  • Dev Stack: Python, Node.js, TypeScript, Go (bonus), FastAPI, Next.js
  • Infrastructure: Docker, Kubernetes, AWS Lambda, ECS, CDK, Terraform
  • Testing & Observability: pytest, Playwright, Datadog, OpenTelemetry, Sentry
  • Security & Compliance: Familiarity with secure-by-design, SOC2, GDPR
  • AI Capabilities: Prompt engineering, tool use, RAG, agentic evaluation, multi-model systems

Bonus Points for:

  • Experience working in a tech company or high-growth startup.
  • Experience building and shipping production agentic systems in consumer or enterprise products.
  • Strong understanding of feedback loops, alignment strategies, and multi-step planning in autonomous agents.
  • Contributions to open-source AI tools or frameworks.
  • Production experience of developing agentic systems using multiple approaches to architecture.
  • Experience integrating AI systems into traditional product stacks with real users.
  • Passion for safety, interpretability, and governance in LLM-driven systems.
  • Willingness to contribute outside of core expertise to drive impactful work forward.
  • Developing infrastructure as code in Go.
  • Familiarity with agile development methodologies (Scrum/Kanban, JIRA).
  • Experience with pair programming and collaborative development techniques.
  • Active contributions to open-source projects or participation in developer communities.

Employee Benefits & Perks

Compensation: Salary + Equity

  • Our salary range for this position is $208k - $280k, 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 (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 

ndividual 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.

If you're excited about driving measurable impact and contributing to a mission that truly matters, we’d love to connect. Join a collaborative, experiment-driven team where your insights, creativity, and product thinking help unlock meaningful growth for our customers and the business. 

About You:

  • You are a technical leader, proficient in TypeScript, React, Next.js, and Node.js, with a strong foundation in system design and cloud-native development.
  • You have a problem-solving mindset, tackling system-wide challenges with strategic thinking and a focus on high-impact solutions.
  • You see AI not as a tool but as a fundamental shift in engineering, and you actively seek opportunities to harness its potential.
  • You thrive in fast-moving, high-performance environments, navigating ambiguity, aligning stakeholders, and delivering results.
  • You are a mentor and collaborator, fostering team growth through thoughtful guidance, clear communication, and constructive feedback.
  • You are passionate about writing maintainable, testable code, ensuring software quality through modern DevOps and observability best practices.

About the Role:

Technical Leadership, Quality & Impact

  • Architect, design, and deliver large-scale, high-performance features across the stack.
  • Drive system-level design and data modeling, ensuring scalable, reliable, and maintainable solutions aligned with organizational best practices.
  • Think expansively about AI—how to build with it, integrate it into features, and leverage it to drive innovation
  • Own technical projects end-to-end, ensuring efficient delivery, optimal performance, extensibility, and reliability.
  • Lead and contribute operational engineering strategies, including test automation observability and modern CI/CD practices.
  • Collaborate on cloud architecture decisions to deliver resilient, cost-effective, and secure solutions.
  • Deliver high-quality, production-ready code that adheres to coding and operational best practices, accounts for edge cases, and is self-documenting for maintainability.
  • Lead efforts to reduce technical debt and optimize system performance through continuous refactoring and advanced debugging practices.
  • Drive improvements in system reliability, scalability, and performance, leveraging monitoring and observability tools to proactively identify bottlenecks and issues.
  • Champion a culture of learning by facilitating design discussions, providing constructive feedback, and fostering collaboration across teams.

Collaboration, Innovation & Mentorship

  • Partner with product managers, designers, and cross-functional stakeholders to align technical efforts with business objectives and customer needs.
  • Mentor engineers across skill levels, providing guidance in software patterns, architecture, DevOps, and problem-solving techniques to foster technical growth.
  • Communicate complex technical topics clearly to both technical and non-technical audiences, ensuring alignment and shared understanding across teams.
  • Promote knowledge sharing through technical documentation, share-outs, and peer collaboration to elevate team capabilities.
  • Actively explore how AI can improve developer efficiency, automate workflows, and enhance system reliability.
  • Explore and advocate for cutting-edge tools and technologies, incorporating them into the engineering stack when appropriate to advance capabilities.
  • Lead initiatives to drive innovation and continuously improve engineering processes, challenging the status quo to deliver greater value.
  • Contribute to system-wide architectural discussions to ensure alignment with strategic goals and future scalability.

Qualifications:

  • 5+ years of professional full-stack development experience in high-performing teams.
  • Demonstrated proficiency in TypeScript, React, Next.js, and Node.js.
  • Advanced skills in system design, data modeling (MongoDB, Postgres), and cloud-native development (AWS).
  • Skilled in test-driven development, CI/CD pipelines, and modern DevOps best practices.
  • Proficient in debugging complex systems and implementing observability practices to ensure operational excellence.
  • Demonstrated ability in integrating AI code assistants to enhance development productivity and code quality, with hands-on experience using at least one of the following: Claude, Cursor, RooCode, or RooCline.
  • Proven ability to mentor engineers, align technical solutions with business goals, and influence cross-functional teams.
  • Strong analytical skills, with a passion for identifying and prioritizing high-impact solutions across engineering challenges.
  • 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), South Carolina (SC), Pennsylvania (PA), Texas (TX), Vermont (VT)

Bonus Points for:

  • Experience in tech companies or high-growth startups.
  • Familiarity with Agile development methodologies (Scrum/Kanban, JIRA).
  • Hands-on experience with Docker, Kubernetes, or other container orchestration tools.
  • Experience with pair programming and collaborative development.
  • Experience integrating AI-assisted workflows effectively into complex software engineering tasks.
  • Contributions to open-source projects or active participation in developer communities.

Employee Benefits & Perks:

  • Compensation: Salary + Equity
    • Our salary range for this position is $148,000 - $185,000, 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
    • 2 dedicated company-wide volunteer days per year
  • 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)
    • Up to $1,000 annually in learning & development reimbursement
  • Extra
    • Flexible work schedule + hours
    • Family-friendly, remote-first environment
    • 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.

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