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Sierra is the leading platform for customer-facing AI agents, serving 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 Salesforce co-CEO and Facebook CTO) and Clay Bavor (former Google Labs lead), Sierra is transforming how enterprises serve customers with AI.
In this Enterprise Sales Engineer role, you will be the primary technical partner to the sales team, responsible for winning deals and scaling customer success. Your responsibilities include:
- Serve as the trusted technical expert throughout the entire sales cycle, from first discovery to deployment
- Scope customer use cases, articulate business value, design and demo Sierra's platform, and lead technical architecture reviews
- Move prospects from discovery to a working, tailored agent in days rather than weeks
- Collaborate directly with Sales, Product, and Agent Engineering teams to drive go-to-market strategy and improve agents through customer feedback
- Develop deep industry expertise and winning sales motions to scale your impact
- Handle multiple concurrent enterprise deals (typically $200-$500k) while maintaining quality
- Leverage AI tools efficiently in your technical sales motion—discovery prep, solution design, demo building, and proposal creation—while owning accuracy of all customer-facing materials
- Communicate complex technical concepts to both technical and non-technical audiences, including executives and technical leaders
You will work in a hybrid model based in Toronto, with the flexibility to collaborate across Sierra's distributed offices.
REQUIREMENTS:
- 3-4+ years of experience in Sales Engineering, Solutions Engineering, or customer-facing technical sales
- Proven experience leading enterprise sales processes with deal sizes ranging $200-$500k
- Demonstrated expertise in demo building, presenting, and GTM functions with customers or clients
- Strong relationship-building skills with prospects at all levels, from executives to technical leaders
- Ability to connect prospect business problems to Sierra's solutions and explain them to technical and non-technical audiences
- Proficiency leveraging AI tools as a regular part of your technical sales workflow
- Track record of managing high deal volume concurrently without compromising quality
- Comfort switching between sub-industries and use cases
- Bachelor's degree or above (Computer Science or related field preferred, or equivalent professional experience)
BONUS QUALIFICATIONS:
- Experience translating code, technical logic, and user requirements into product and engineering requirements
- Prior experience selling technical AI products
