Enterprise Sales Engineer in Toronto

Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands 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.

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.

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.
• 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.
• Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones.
• Craftsmanship: We get the details right, from the words on the page to the system architecture.
• Intensity: We know we don’t have the luxury of patience. We play to win.
• Family: We know that balance and intensity are compatible, and we model it in our actions and processes.

What we offer:

• 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.
• Discretionary benefit stipend giving people the ability to spend where it matters most.
• Free alphorn lessons.

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 encourage you to apply even if your experience doesn't precisely match the job description.