Software Engineer, Agent - Insurance

About the Financial Services team

• Our financial services customers span insurers that provide protection for life’s most challenging moments, systemically important banks, neobanks committed to building more delightful banking software, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity.

• Our Financial Services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle—the hours after a family discovers their home has been damaged by a wildfire and begins filing a claim; the difficult conversation following the loss of a loved one as beneficiaries navigate a life insurance claim; the frustration of dropping a phone, shattering the screen, and trying to quickly understand coverage and arrange for a repair or replacement.

• Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone.

What you’ll do

• Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.

• Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.

• Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.

• Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.

Example projects

These are some examples of projects that engineers on our team have worked on recently:

• Design and build AI agents for large insurance companies that consistently outperform human agents in filing claims quickly and consistently.

• Develop and refine AI agents capable of navigating complex customer interactions, like generating a quote for insuring a modified 1960s Corvette.

• Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!

• Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development

• Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers

What you'll bring

• Experience building and scaling end-to-end production systems.

• Strong technical problem-solving skills, especially in fast-changing, ambiguous environments.

• A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship.

• Comfort working directly with customers to understand their needs and solve real-world problems.

• Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences.

• Genuine interest in Financial Services and improving the end customer experience. Experience in insurance technology, implementations at financial institutions, working inside of these institutions or familiarity with financial services security and compliance requirements (coverage advice, PII handling, etc.) are a strong plus.

Even better...

• Experience building or deploying AI/LLM systems in production

• Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed

• Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering

• Prior experience with React, TypeScript, and/or Go

• Previous roles where you interfaced with customers or led technical projects with external stakeholders

Our values

• Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.

• Flexible (unlimited) paid time off

• Life insurance and disability benefits

• Retirement plan dependent on country of employment

• Parental leave

• Fertility and family building benefits through Carrot

• Free alphorn lessons