Enterprise Sales Engineer, Financial Services
Sierra· enterprise· Customer Experience AI· Oct 23, 2026 · 4d ago
Toronto · Canada
In office
Full-time
Principal
$124K–$178K est.
3+ years exp
Job description
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 linkedin.com and Clay Bavor linkedin.com. 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 modern 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
- 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
- Go deep on your industry, the patterns, and winning motions to scale your work
WHAT YOU'LL BRING
- 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
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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Keywords to mirror
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Benefits
Benefits detected in the listing.
Dental
Vision
Paid Time Off
Parental Leave