Note: The job is a remote job and is open to candidates in USA. Whippy is a bootstrapped, profitable AI-native platform for business communication serving more than 1,000 customers, with deep expertise in staffing and HR. The Account Executive will own the full sales cycle, build an independent pipeline, close and expand accounts, manage territory strategy, and collaborate with the CEO and engineering team to shape the company's sales organization and product direction.
Responsibilities
- You own the entire cycle: sourcing, discovery, demo, business case, negotiation, close, and the expansion inside the account after
- You build pipeline through outbound, referrals, partners, conferences, and your own relationships
- You work directly with our CEO on deals, territory strategy, and how we scale the sales organization
- You work directly with engineering, because customer feedback here does not disappear into a ticketing system. It shapes what gets built next
- We expect you to decide where your time is best spent
- We expect you to know which deals are real and which are wasting your time, and to pressure test your own pipeline instead of waiting for someone else to do it
- We expect you to ask for help before a deal needs rescuing, and to come to the CEO with a point of view, not wait for instructions
- If something in our sales process is broken, we expect you to notice it and help us fix it
- First 30 days: you show us a target list we did not give you
- First 90 days: you are running complete cycles independently and closing your first deals
- Year one at plan: $1M+ in new ARR closed
- Perform, and you help pick the next AE and shape the team that follows
Skills
- Remote (East Coast mornings)
- We are looking for an exceptional Account Executive who can build their own pipeline, think strategically about their territory and deals, and help us shape the sales organization that comes next
- If you can own the 8am ET calling block, we do not care what time zone you sleep in
- You have personally closed meaningful B2B software revenue and can explain exactly how you created and won those deals
- Your buyer has been the owner, executive, or operator who signs the check and only responds to measurable ROI
- What matters is that you know how to sell to skeptical, fast moving operators
- You cannot consistently work East Coast mornings
- If you have sold into staffing or HR technology, that is valuable, because you may already know many of our buyers
Benefits
- Uncapped commission.
- Remote role.
- Outperform, and $300K+ in annual earnings is absolutely on the table.
Company Overview