Sales Engineer

Letter AI, Inc.; Chicago, Northern (IL, KY); Hybrid; USD 110,000 - 175,000; Full time

Benefits offered by this job

Stock options

Comprehensive medical, dental, vision

401(k) with company match

Daily lunch in Chicago and SF offices

Team events

Job summary

Letter AI, Inc. in Chicago is seeking a Sales Engineer to bridge strategy and technical messaging, delivering strategic custom demos and coordinating with Account Executives to close high-ARR opportunities.

You will tailor demonstrations to customer needs and showcase the value of Letter AI’s AI-powered revenue enablement platform. You will travel on-site about once a month, build branded demo environments on Letter AI’s zero-code platform, and tell a compelling story that positions Letter AI as

Qualifications

• Proven Presales Experience in SaaS or enterprise tech.
• Exceptional presentation skills and storytelling ability.
• Deep understanding of enablement personas and related pain points.
• Attention to visual detail when building slides, demos, and microsites.
• Practical understanding of AI concepts and integrations without coding.
• Comfortable in a fast-growth startup and willing to travel for high-value opportunities.

Responsibilities

• Deliver strategic, custom demos for high-dollar accounts.
• Build fully customized demo environments and microsites for prospects.
• Command the room in person or virtual settings, including C-level audiences.
• Partner with Account Executives to qualify technical/strategic requirements and drive vendor-of-choice outcomes.
• Represent Letter AI on-site, traveling ~monthly to meet prospects and attend events.

Skills

Presales experience

Masterful presenter

Enablement domain knowledge

Design acumen

AI fundamentals

Startup-adaptable mindset

Job description

View all jobs Sales Engineer Chicago Sales Hybrid Full-time

About Letter AI

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.

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.

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 Operate

• 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: $110k–$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