Whippy is the AI-powered communication platform transforming how businesses engage across all communication channels. Companies rely on Whippy’s AI Voice & Chat, Messaging, Business Phones, and Workflow Automations to eliminate manual work—responding to inquiries, screening applicants, nurturing leads, collecting reviews, and driving revenue at scale. With intelligent automation and an all-in-one messaging suite, Whippy replaces multiple tools and empowers teams to work smarter, faster, and more efficiently.

Whippy

The all-in-one communication platform, elevating business productivity with automation and AI-driven technology.

Account Executive at WhippyRemote (East Coast mornings) | Uncapped commission. 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. We want someone who already knows how to manage themselves.
Why WhippyWhippy 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. That is the kind of platform great Account Executives want to sell.
How we workBootstrapped and profitable, so revenue is the strategy, and your commission comes from customers, not a burn rate.No task is above or beneath anyone here, including the CEO, who still cold calls.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 jobYou 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 perfectly documented 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.
You will need to manage yourselfWe 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.What success looks likeFirst 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. Outperform, and $300K+ in annual earnings is absolutely on the table.Perform, and you help pick the next AE and shape the team that follows.
Who succeeds hereYou 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 ifYou 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 nowYou 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.
