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 Financial Services team

Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world's leading banks use Sierra), insurers that provide protection for life’s most challenging moments, 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 contemporary tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one.

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

Be the primary partner to your Sales counterparts helping to win deals and grow customers

Go from first discovery to a tailored, working agent in days, not weeks, across prospects and existing customers

Work with every team involved in the decision: CX, IT, security, procurement, and executive sponsors

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

Mentor newer SEs and contribute reusable assets for your industry or team

Stay with the account after the sale, through the Agent Development handoff, launch,



and expansion to new use cases

Go deep on your industry, the patterns, and winning motions to scale your work

What you'll bring

4-6+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales

Experience in leading the sales process with large Enterprise customers with deal sizes ranging $500-$1M

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

Experience in relationship-building with prospects, including executives and technical leaders

Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience

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

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 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.

📌 Enterprise Sales Engineer (Toronto)
🏢 Sierra
📍 Toronto