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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 was founded by Bret Taylor (former co-CEO of Salesforce, CTO of Facebook, Google Maps co-creator) and Clay Bavor (18-year Google veteran who led Google Labs and AR/VR initiatives).
In this 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 main technical point of contact throughout the entire sales cycle, from initial discovery through deal closure
- Rapidly scope customer use cases and design tailored AI agent solutions, moving from discovery to working demos in days rather than weeks
- Lead technical and architecture reviews, articulating business value to both technical and non-technical audiences
- Own the end-to-end pre-sales process: discovery, solution design, platform demonstrations, and technical proposal development
- Collaborate closely with Sales, Product, and Agent Engineering teams to drive go-to-market strategy and inform product development through customer insights
- Develop deep industry expertise and winning sales motions to scale your impact
- Manage a high volume of concurrent deals (typically $200-$500k enterprise contracts) while maintaining quality
- Leverage AI tools efficiently in your sales motion—discovery prep, solution design, demo building, and proposal creation—while owning accuracy of all customer-facing materials
The role is based in Toronto with Sierra's primary presence in San Francisco and growing offices across North America, Europe, and Asia.
REQUIREMENTS:
- 3-4+ years of experience in Sales Engineering, Solutions Engineering, or customer-facing technical sales
- Proven track record leading enterprise sales processes with deal sizes in the $200-$500k range
- Demonstrated expertise in demo building, presenting, and GTM functions
- Strong relationship-building skills with prospects at all levels, including C-suite and technical leaders
- Ability to translate complex technical concepts and business problems into clear value propositions for both technical and non-technical audiences
- Proficiency with AI tools as a regular part of your workflow, with accountability for accuracy
- Ability to manage multiple concurrent deals across different sub-industries and use cases without compromising quality
- Bachelor's degree or equivalent professional experience (Computer Science or related field preferred)
BONUS QUALIFICATIONS:
- Experience translating code, technical logic, and user requirements into product and engineering specifications
- Prior experience selling technical AI products
