Empower your revenue teams to win more deals, faster. Get our all-in-one revenue enablement platform that unifies content, training, coaching, and buyer engagement. Backed by Battery and Y Combinator.
About the role
As a Sales Engineer at Letter AI, you will be an artful seller and trusted technical advisor during the most strategic phases of our sales process. We are looking for someone a phenomenal presenter who can command the room and tell an inspiring story. You will partner closely with Account Executives on strategic, high-ARR opportunities to build custom, branded demo environments and bespoke buyer microsites, driving prospects to make Letter AI their vendor of choice.
What they're looking for
- Proven Presales Experience: Prior experience as a Sales Engineer, Solutions Consultant, or Solutions Engineer in SaaS (enterprise tech or sales/revenue enablement space highly preferred)
- Masterful Presenter & Storyteller: Exceptional presentation skills with the ability to captivate audiences, simplify complex concepts, and build an emotional connection to the product's value
- Domain Expertise in Enablement: Deep understanding of the enablement persona (Sales Enablement Managers, VPs of Enablement, Revenue Ops) and their key operational pain points is a bonus
- Solid Eye for Design: Impeccable attention to detail when building custom slides, demo environments, and buyer microsites—ensuring polished, visually compelling customer collateral every time
- Strong AI Fundamentals: Practical understanding of AI concepts, AI integrations, and modern architecture (e.g., understanding agent connections, MCP servers, and generative AI capabilities) without needing to write code
- Startup-Scrappy & Adaptable: Comfortable in a high-growth, fast-moving environment with an agile mindset and willingness to jump on a plane when high-value customer opportunities arise
More about this role
Letter AI is the world’s first revenue enablement platform powered natively by AI. We’re reimagining the end-to-end revenue journey by turning real customer conversations and account data into actionable insights, personalized coaching, meeting prep, and next steps.
Revenue teams aren’t asking for more content or tools. They’re asking for better outcomes. Letter does just that, empowering them to learn faster, sell smarter, and win more.
We recently raised a $40M Series B and are already helping leading companies like Adobe, Lenovo, and Figma transform how their teams work. We 10xed our revenue last year and are looking for the best of the best in Chicago to help us build on that momentum.
As a Sales Engineer at Letter AI, you will be an artful seller and trusted technical advisor during the most strategic phases of our sales process. We are looking for someone a phenomenal presenter who can command the room and tell an inspiring story. You will partner closely with Account Executives on strategic, high-ARR opportunities to build custom, branded demo environments and bespoke buyer microsites, driving prospects to make Letter AI their vendor of choice.
- Ground-Floor Influence: As...
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