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Enterprise Sales Engineer - Majors

Sierra - Toronto, ON, Canada - Hybrid - posted 2026-10-23

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Sierra is a leading platform for customer-facing AI agents, working with major brands including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. The company is headquartered in San Francisco with growing offices across North America, Europe, and Asia. Founded by Bret Taylor (former co-CEO of Salesforce, CTO of Facebook, co-creator of Google Maps) and Clay Bavor (18-year Google veteran who led Google Labs and Google's AR/VR efforts), Sierra is transforming how enterprises serve customers with AI. As an Enterprise Sales Engineer, you will be the primary technical partner to your sales counterparts, owning the end-to-end technical pre-sales process. Your responsibilities include scoping customer use cases, articulating business value, designing and demoing Sierra's platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle. You will work with every team involved in purchasing decisions—CX, IT, security, procurement, and executive sponsors—and move from first discovery to a tailored, working agent in days, not weeks. You'll mentor newer sales engineers, contribute reusable assets for your industry or team, and stay with accounts through agent development, launch, and expansion to new use cases. You'll go deep on your industry, understand winning patterns, and scale your work accordingly. Sierra's culture is built on five core values: Trust (accountability, empathy, quality, responsiveness), Customer Obsession (deeply understanding business goals and relentlessly driving outcomes), Craftsmanship (getting details right and taking pride in products), Intensity (playing to win and continuously improving), and Family (balancing intensity with work-life balance and supporting each other). QUALIFICATIONS: - 4–6+ years of experience in Sales Engineering, Solutions Engineering, or customer-facing technical sales - Proven experience leading the sales process with large Enterprise customers on deals ranging $500K–$1M - Demonstrated expertise in demo building, presenting, and working with customers in GTM functions - Strong relationship-building skills with prospects, including executives and technical leaders - Ability to connect a prospect's specific business problems to Sierra's solutions and explain them to both technical and non-technical audiences - Proficiency in leveraging AI tools as a regular part of your technical sales motion (discovery prep, solution design, demo and prototype building, technical proposals), with ownership of accuracy - Experience growing accounts past initial sale - Bachelor's degree or above (bonus if in Computer Science or related field, or equivalent professional experience) - Bonus: Experience translating code, technical logic, and user requirements to product and engineering requirements; experience selling technical AI products

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