Founding Account Executive

Founding Account Executive — Espy

Espy | Contract-to-Full-Time | Full-Time Hours | Ideally local (ATL), Open to remote

The Opportunity

Espy is a fast-growing B2B corporate gifting company (espybox.com) helping sales, HR and marketing leaders build stronger relationships through curated, high-end gift boxes tailored to recipients using deep research. We doubled revenue this year, are at capacity with inbound demos and are now building out our sales team from the ground up — starting with one person.

This isn't a typical sales job. It's a founding seat on a team that doesn't exist yet. You'll work directly with the founder, close real deals from day one, and have the opportunity to grow into a leadership role – building and eventually running or being a major contributor to the sales team you helped start.

If you want a job where you learn the whole business, not just a script – how a company sells, prices, operates, and scales, together with the ability to grow fast – this is the job for you.

What You'll Do

• Run a full calendar of qualified, inbound sales demos 
• Close new accounts through a consultative, relationship-first sales process.
• Work closely with the founder to learn not just how to sell, but how the business itself works — pricing, operations, fulfillment, what success for our clients looks like.
• Help shape the sales process itself as one of the first people to run it at scale — your feedback will directly influence how the next reps are trained.

What Makes This Different

• We will fill your calendar with demos — your job for the trial is to close, and with extremely light prospecting. You'll have a minimum of 10 demos a week.
• Real growth path. Strong performers move toward full-time employment, expanded ownership of the sales function, and the opportunity to lead a team as Espy scales.

Who We're Looking For

• Someone ambitious, and driven.
• Comfortable running consultative conversations over video, confident and direct.
• Excited by the idea of building something, not just filling a seat — you want a stake in how this team comes together.
• Reliable, communicative, and eager to succeed and develop.

Compensation

• $3,000 per month + a 9% commission on every closed new deal (initial deal sizes typically around $3,000 – $15,000) and and 5% trailing commission on initial pilots that convert into recurring business (annual agreements or recurring deals typically range from $10,000–$50,000, with potential for significantly larger accounts)
• Structured as a contract role during an initial trial period, with a clear path to full-time employment for strong performers
• OTE: $80,000-$120,000 uncapped

What Happens After the Trial

The 90-120 day trial period exists to test and prove fit for full-time employment at Espy. If performance goals are met, the following will be discussed and may be implemented:

• Transition to W-2 employment
• Evaluation of compensation structure
• Expanded scope and responsibility as part of Espy's growing sales team

Why Now

Espy is at an inflection point — proven product, growing demand, and a real plan to scale. The person who takes this role isn't just filling a sales seat; they're helping build the team and process that Espy's next chapter runs on.

Ready to grow with us? Email dan@espybox.com