Sales Engineer

About Letter AI

Letter AI is the world s first unified revenue acceleration platform powered natively by generative AI. Our platform empowers sales teams at customers like Lenovo and Redpanda to ramp up faster with AI-powered training and coaching, instantly find and personalize collateral for customers, and engage their buyers with the industry's first AI Sales Room. We recently raised a $40M Series B led by Battery Ventures, with participation from existing investors including Y Combinator, Lightbank, Northwestern Mutual Future Ventures, Stage 2 Capital, and Formus.

The round comes just four months after announcing our Series A, indicating a shift we re seeing in real time: revenue teams aren’t asking for more content or tools. They’re asking for better outcomes, and Letter AI is bringing those outcomes to life! We 10

Xed our revenue last year and are looking for the best of the best in Chicago to join us on the adventure.

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 our third dedicated Sales Engineer, you’ll work side-by-side with our founding SE and leadership team to shape how our presales function scale and execute.
• Massive Upside & High Growth: Be part of a fast-moving, hyper-growth AI company where your individual contribution directly drives high-dollar deal wins and revenue acceleration.
• Master the Artful Sell: Move beyond traditional technical checklists. You ll lead custom, highly strategic presentations that position Letter AI as an indispensable revenue acceleration platform.
• Hands-on AI Integration: Deepen your expertise in generative AI, agent workflows, and AI integrations in a zero-code environment that emphasizes business impact and enablement domain knowledge.

• Deliver Strategic, Custom Demos: Lead post-discovery technical and strategic presentations for strategic, high-dollar target accounts (ranging from hyper-growth startups to 20,000-person enterprise prospects).
• Build Custom Demo Environments: Leverage Letter AI’s zero-code platform and internal tools to build fully customized demo instances and tailored microsites for every prospect. No generic stock demos or 50 open browser tabs.
• Command the Room: Present powerfully across all settings—whether delivering a high-stakes custom demo to C-level executives or speaking to a crowd of hundreds at industry conferences and enablement strategy sessions.
• Partner for Deal Closure: Collaborate closely with Account Executives to qualify technical/strategic requirements and secure "vendor of choice" status before handoff for final negotiations.
• Represent Letter AI On-site: Travel (~once a month or as needed) to meet prospects on-site, attend company offsites (e.g., California), join SKO events, and participate in key customer strategy sessions.

• 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…