Staff AI Agent Software Engineer - San Diego - Trust & Will

Description

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 CI/CD 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.
• 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.
• Mentor 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, , 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 CI/CD, 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
• Security & Compliance: Familiarity with secure‑by‑design, SOC2, GDPR

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

• 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.
• 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 For more information, visit our privacy policy.

As set forth in Trust & Will's Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.