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.

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:

• 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.
• 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.
• 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.
• 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.

Be you, with us: 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 believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team.