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.

We are guided by a set of values that are at the core of our actions and define our culture: 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.

Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. 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

- Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.

- Retail is also where AI agents go beyond support to generate revenue.



From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.

- Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.

What you'll do

- Go deep on a few accounts. Learn each customer's business well enough that you could be wearing their badge in their hallways

- Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle

- Decide when to bring in Agent Development, Product, Security, Legal, and Sierra leaders, and what each of them needs to do. You keep everyone aimed at the same goal

- Raise the bar for the SE team: mentor others, set standards for demos and pilots, and write the playbooks for Strategic deals and GTM processes

- Stay with the account after the sale, through the Agent Development handoff, launch, and expansion to new use cases





- Share what you see across your largest accounts with Product leadership and inform roadmap

What you'll bring

- 7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales

- Experience in leading the sales process with Strategic customers with deal sizes of $1M+ consistently

- Past experience in demo building, and presenting, and working with customers or clients in the GTM function

- Strong experience in relationship-building with prospect stakeholders, including C-suite executives and technical leaders

- Experience leading architecture, integration, and security discussions with enterprise architects, engineering leaders, and security teams

- Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it

- Experience growing accounts past initial sale and defining customer roadmaps to facilitate growth

- Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience

Even better...

- Experience translating code, technical logic and user requirements to product and engineering requirements

- Selling a technical AI product

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 practical. We build trust with each other by showin

📌 Enterprise Sales Engineer (Toronto)
🏢 Candidate
📍 Toronto