Sales Engineer in Chicago, Illinois at Letter AI

About Letter AILetter AI is the world's first unified revenue acceleration platform powered natively by generative AI. Our platform empowers sales teams at customers like Adobe, Lenovo, and Figma 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 10Xed our revenue last year and are looking for the best of the best in Chicago to join us on the adventure 📈.
The RoleAs 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.
Why Join?

• 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.

What You'll Do

• 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.

Qualifications for the Role

• 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.

How We OperateAt Letter AI, we operate by a set of core principles:

• Customer-obsessed: Make your customers unreasonably happy and everything else will fall into place
• Ambitious yet practical: Set big goals, but stay grounded with disciplined execution and ruthless prioritization
• Direct yet kind: Never hold back from speaking your mind, but do so in a way that is kind to your colleagues
• Driven yet humble: Push for excellence and deliver fast, but keep your humility

What’s in it for you?

• Compensation: $110–$175k base salary, depending on experience, expertise, and expected impact, plus variable compensation
• Ownership: Every full-time teammate receives Letter stock options, so you can share in the value you help create
• Benefits that have you covered: Comprehensive medical, dental, and vision coverage, plus a 401(k) with company match
• Benefits for the everyday: Company-supported commuter, connectivity, and wellness benefits, plus daily lunch in our Chicago and San Francisco offices
• Team events: Happy hours, dinners, events, and offsites with a team that genuinely enjoys spending time together
• Build with us: Join a fast-growing startup where you’ll have meaningful ownership and impact, working closely with top-notch teammates to help build and scale Letter