Sales Engineer

Letter AI • Chicago, IL

18d • $110,000 - $175,000 • Hybrid

About The Position

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.

Requirements

• 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.
• 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.

Nice To Haves

• 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.

Responsibilities

• 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.

Benefits

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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed