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Salary
$232k – $239k per year
Location
In office (Toronto)
Seniority
Middle · 4+ years exp
Employment
Full-Time

Confirmed on the employer's own hiring board on Nov 6, 2026. First seen by Alion on Oct 23, 2026. Sierra scores A on the Alion truth index.

Overview
Company
Impact
Profile match
Sierra is an American artificial intelligence company founded in 2023 by Bret Taylor, the former co-chief executive of Salesforce and chairman of OpenAI, together with a former Google engineering leader. It builds conversational agents that handle customer service interactions end to end for large consumer businesses, resolving issues by acting on the company's own systems rather than only answering questions, and it charges per resolved outcome rather than per seat. Headquartered in San Francisco and privately held at a multi-billion dollar valuation, it works with retailers, telecommunications operators, financial services firms and healthcare providers.

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.

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.

  • 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.

  • Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.

  • Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.

  • Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.

What we offer

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 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

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.

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

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