Account Executive

Account Executive at Whippy

Remote (East Coast mornings)

180-200K OTE (50/50 split), uncapped above quota.

Top performers will earn $300K+. We pay for production, not tenure.

Over the last 90 days, our founder led sales motion booked nearly $1M in ARR across new customers and expansion.

The opportunity is proven. The sales organization is not finished.

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. This is not a role where a sales manager tells you what to do every morning. When you see an open lane, we expect you to run with it.

Why Whippy

Whippy is the AI native platform for business communication: AI Voice Agents, AI Recruiting, messaging, VoIP, deep integrations, and our own workflow engine in one system. Our customers do not buy software that helps their employees do the work. They buy AI that does the work.

Our deepest market today is staffing and HR, where we are the category leader, and new verticals are already opening behind it. We serve more than 1,000 customers, with an engineering team larger than the rest of the company combined. Customers like Your Employment Solutions and Staffworks have each generated more than $1M in measurable value using Whippy, and those are named, public case studies you get to sell with.

It is common to land a $50K ARR customer and expand that relationship by another $100K or more over time.

How we work

Bootstrapped and profitable, so revenue is the strategy, and your commission comes from customers, not a burn rate.

Leadership stays close to the pipeline. Our CEO still cold calls, so you'll never be selling in a vacuum.

AI first in how we sell, not just what we sell. We expect you to use AI to move faster in prospecting, prep, and follow up.

Speed over polish. Results over activity.

The job

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.

There are no SDRs filling your calendar, no manager checking your activities, and no rigid playbook. You inherit a product customers want, active pipeline, and proof the motion works. Some people read that as risk. You should read it as freedom.

Remote role. Our customers run on East Coast time, so your mornings do too. If you can own the 8am ET calling block, we do not care what time zone you sleep in.

We expect you to operate independently

You will have clear revenue expectations, deal qualification criteria, and regular pipeline and deal reviews with the CEO. Within that structure, we expect you to decide where your time is best spent, know which deals are real and which are wasting your time, and pressure test your own pipeline. Ask for help before a deal needs rescuing, and come with a point of view rather than waiting for instructions. If something in our sales process is broken, notice it and help us make it better.

What success looks like

• 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. Beat plan, and $300K+ is real math, not a recruiting line.
• Perform, and you help pick the next AE and shape the team that follows.

Who succeeds here

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. You get prospects to calculate their own ROI out loud, you book the next meeting before ending the current one, and you would rather pick up the phone or get on a plane than send a fourth follow up email.

If you have sold into staffing or HR technology, that is valuable, because you may already know many of our buyers. It is not a requirement. What matters is that you know how to sell to skeptical, fast moving operators.

This is not for you if

• You want leads handed to you or a manager telling you what to prioritize.
• You need every process documented before taking action.
• You want to sell one simple product the same way every day.
• You cannot consistently work East Coast mornings.

Why join now

You are not joining a company trying to figure out whether customers will buy. They already are. You are also not joining a mature sales organization where every decision has been made. It has not.