Software Engineer, Agent - Retail

About the Retail Team

• The Retail team on Agent Engineering supports some of the largest and most storied consumer brands in the world – including Gap, Wayfair, Sonos, and ADT. Together, we’re reinventing what commerce looks like in this new, AI-first era. Our customers rely on us to not only deliver novel experiences, but also host hundreds of millions of shopper and vendor interactions across web, app, phone, and in-store channels every year.

• Our team supports our customers’ customers in the moments that matter – whether that's guiding a shopper to the right product during a limited drop or a Black Friday surge, locating a package that never arrived, or troubleshooting an appliance that stopped working. Always true to each brand’s voice, we create seamless experiences that resolve issues, drive revenue, increase lifetime value, and build lasting loyalty.

• Our team supports our customers' customers in the moments that matter most, from product discovery and checkout to order tracking and troubleshooting. Always true to each brand’s voice, we create seamless experiences that resolve issues, drive revenue, increase lifetime value, and build lasting loyalty.

• Every engineer on the Retail Team is a product-led thinker; every PM on Retail is also tinkering and developing tangible prototypes; and every strategist on Retail is capable of owning an agent end to end. As a part of this team, you'll set the standard on what it means to go beyond your role, and help build the groundwork for the retail industry in the future.

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:

• Abstracting complex commerce systems into packages: Modernize the sprawl of order management, fulfillment, returns, and warranty systems behind the large retailer ecosystem by creating scalable packages that optimize looking up and updating orders for customers – from Shopify storefronts to decades-old homegrown Order Management System (OMS) and claims platforms.

• Shipping the full discovery-to-checkout lifecycle: Build personalized shopping flows that carry a shopper from a vague idea to a completed order. This includes everything from building a recommendation engine that combines transcript-aware planning, structured filters, and semantic and keyword search to payment and order placement.

• Building production-grade agents at a truly global scale: Sierra’s retail agents serve some of the world’s largest global brands, handling traffic at unprecedented volumes during the busiest times of the year and across all geographic locales. You will be building at the frontier of enterprise applied AI.

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.

• Excitement in the retail space and a care for helping some of the world’s top brands continue to build brand loyalty with their customers.

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

• Free alphorn lessons