Sales Engineer

About Letter AI

The Role

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.

• 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

• 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
• 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