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Salary: USD 130,000 - 160,000 / annual
Letter AI is a unified revenue acceleration platform powered by generative AI, serving enterprise customers like Adobe, Lenovo, and Figma. The company recently raised a $40M Series B led by Battery Ventures and has 10Xed revenue year-over-year. You will join as an Enterprise Account Executive in Chicago, taking full ownership of the sales cycle from prospecting through closing deals.
In this role, you will manage the complete sales cycle with autonomy and strategic ownership. You'll identify and pursue new business opportunities through outreach, networking, and creative lead generation, developing tailored sales strategies that address specific customer pain points. You'll build relationships with key decision-makers at target companies and work closely with the CEO and team to iterate on sales approaches, messaging, and market feedback. This is a greenfield opportunity to penetrate an underserved market and drive significant top-of-funnel activity while converting early adopters.
Letter AI operates on core principles: customer-obsessed, ambitious yet practical, direct yet kind, and driven yet humble. You'll work in a fast-paced startup environment where you can wear multiple hats, experiment with new approaches, and meaningfully shape the go-to-market function. The company is recognized as the fastest-growing AI startup in Chicago.
Compensation includes a base salary of $130,000–$160,000 depending on experience and expected impact, plus variable compensation. All full-time teammates receive stock options. Benefits include comprehensive medical, dental, and vision coverage with 401(k) company match, commuter and wellness benefits, daily lunch in Chicago and San Francisco offices, and team events including happy hours, dinners, and offsites.
QUALIFICATIONS:
- 5+ years of experience in SaaS sales or related fields
- Experience selling global enterprise sales or enablement solutions (strong plus)
- Proven track record of exceeding sales quotas and driving revenue growth
- Ability to manage the complete sales cycle with a strategic approach
- Strong interpersonal and communication skills with grit to "figure things out" on the fly
- Independent, proactive, and comfortable in fast-paced, ambiguous startup environment
- Ready to wear multiple hats and take on additional responsibilities as company grows
