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.

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

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

Work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy

3-4+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.

Experience in leading the sales process with Enterprise customers with deal sizes ranging $200-$500k





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 A track record of handling a high number of deals concurrently without cutting quality, and comfortable switching between sub-industries and use cases

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

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

Selling a technical AI product

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 advantages 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 benefits 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. #

📌 REMOTE Sales Engineer - Technical Sales (Toronto)
🏢 Candidate
📍 Toronto