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Enterprise Sales Engineer - Majors, Retail

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

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Sierra is the 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. The Retail team at Sierra partners with a large and growing number of retailers spanning apparel, beauty, grocery, big-box, home and auto, consumer services, marketplaces, and consumer technology. Sierra's agents help millions of shoppers daily with order tracking, returns, product discovery, service booking, and issue resolution. Beyond support, the platform generates revenue through product discovery, personalized recommendations, cart recovery, win-back campaigns, and in-store support. As an Enterprise Sales Engineer for the Retail vertical, you will be the primary technical partner to Sales counterparts, helping to win deals and grow customer accounts. You will own the end-to-end technical pre-sales process: scoping customer use cases, articulating business value, designing and demoing the Sierra 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 working agent in days, not weeks. You will mentor newer Sales Engineers, contribute reusable assets for your industry, and stay with accounts through Agent Development handoff, launch, and expansion to new use cases. You will go deep on retail industry patterns and winning motions to scale your work. REQUIREMENTS: - 4–6+ years of experience in Sales Engineering, Solutions Engineering, or customer-facing technical sales - Experience leading the sales process with large Enterprise customers with deal sizes ranging $500K–$1M - Demonstrated experience in demo building, presenting, and working with customers in the GTM function - Ability to build relationships 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 - 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), 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 a technical AI product

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