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. Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.

Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens.

Before that, Clay led the product and design teams for Google Workspace. 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. Our team supports our customers’ customers in the moments that matter most, from product discovery and checkout to order tracking and troubleshooting.

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. 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.

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. 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: 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 : 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.

Experience building and scaling end‑to‑end production systems. Strong technical problem‑solving skills, especially in quick‑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.

Experience building or deploying AI/LLM systems in production 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 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.

Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.

We care about our product being the best, and when it isn’t, we fix it. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.

We want our benefits to reflect our values and offer the following to full‑time employees: Flexible (unlimited) paid time off Medical, dental, and vision benefits for you and your family Life insurance and disability benefits Retirement plan dependent on country of employment Parental leave Fertility and family building benefits through Carrot Lunch, as well as delicious snacks and coffee to keep you energized These benefits are further detailed in Sierra’s policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or advantages plans. Eligible full‑time employees can participate in Sierra’s equity plans subject to the terms of the applicable plans and policies. We’re working to bring the transformative power of AI to every organization in the world.

To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national‑origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class. #

📌 Software Engineer, Agent - Retail (Toronto)
🏢 Sierra
📍 Toronto