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Sierra is a leading platform for customer-facing AI agents, serving major brands like 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 Salesforce co-CEO, Facebook CTO, Google Maps co-creator) and Clay Bavor (18-year Google veteran, led Google Labs and AR/VR initiatives), Sierra is transforming how enterprises serve customers with AI.
In this role, you will own the end-to-end technical pre-sales process for strategic enterprise accounts. You'll go deep on a small number of high-value accounts, learning each customer's business thoroughly. 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'll coordinate cross-functional resources—Agent Development, Product, Security, Legal, and Sierra leadership—keeping everyone aligned on deal objectives. You'll raise the bar for the SE team by mentoring others, setting standards for demos and pilots, and developing playbooks for strategic deals and GTM processes. Your involvement extends beyond close: you'll stay with accounts through Agent Development handoff, launch, and expansion into new use cases. You'll also share insights from your largest accounts with Product leadership to inform roadmap decisions.
The ideal candidate brings 7+ years of Sales Engineering, Solutions Engineering, or customer-facing technical sales experience, with a proven track record leading strategic deals consistently sized at $1M+. You have strong demo-building and presentation skills, with experience in GTM functions. You excel at relationship-building with C-suite executives and technical leaders, and you're comfortable leading architecture, integration, and security discussions with enterprise architects, engineering leaders, and security teams. You're proficient with AI tools as part of your technical sales motion—using them for discovery prep, solution design, demo and prototype building, and technical proposals—while owning the accuracy of everything you present to customers. You have experience growing accounts beyond initial sale and defining customer roadmaps for expansion. A Bachelor's degree is required; Computer Science or related field is a bonus, as is equivalent professional experience. Additional strengths include the ability to translate code, technical logic, and user requirements into product and engineering requirements, and prior experience selling technical AI products.
Sierra's culture is built on five core values: Trust (accountability, empathy, quality, responsiveness), Customer Obsession (deeply understanding business goals, relentlessly driving outcomes), Craftsmanship (attention to detail, continuous improvement), Intensity (playing to win, fixing problems quickly), and Family (balancing intensity with work-life balance, supporting parents and personal achievements).
REQUIREMENTS:
- 7+ years in Sales Engineering, Solutions Engineering, or customer-facing technical sales
- Proven experience leading strategic deals consistently sized at $1M+
- Demonstrated expertise in demo building and GTM presentations
- Strong relationship-building skills with C-suite and technical leaders
- Experience leading architecture, integration, and security discussions with enterprise teams
- Proficiency with AI tools for discovery, solution design, demo building, and proposals (with accountability for accuracy)
- Track record of account growth and customer roadmap development
- Bachelor's degree or above (Computer Science or related field preferred; equivalent professional experience acceptable)
- BONUS: Experience translating code and technical logic to product/engineering requirements; prior AI product sales experience
