Software Engineer, Agent - Insurance

About Us

Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands—including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank—to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.

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, and more. Our Financial Services team partners closely with these organizations to set their AI strategies and build modern tools that handle moments when a person’s private anxiety meets an institution’s procedural muscle.

What You'll Do

• Design and deliver production-grade AI agents: Build and ship highly performant, reliable, and intuitive AI agents that are mission-critical and drive revenue directly to Sierra's growth.
• Drive the Agent Development Life Cycle (ADLC): Take complete ownership and autonomy from initial pilot through deployment and continuous iteration, defining standards for ADLC best practices.
• Partner with large enterprises and cutting-edge startups: Work directly with leaders at major enterprises and startups to understand their business challenges and embed AI agents across their business stack.
• Build the future of the platform: Surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform teams to guide the evolution of Sierra's core platform.

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—finding 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 customer experience.

Even Better

• Experience building or deploying AI/LLM systems in production.
• Background as a founder or founding engineer balancing craft, ownership, and speed.
• Familiarity with tools that power modern AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering.
• Prior experience with React, TypeScript, and/or Go.
• Previous roles interfacing with customers or leading technical projects with external stakeholders.
• Experience in insurance technology, implementations at financial institutions, or familiarity with financial services security and compliance requirements (coverage advice, PII handling, etc.).