Founding Account Executive – Whippy

Remote (East Coast hours)

$200K OTE ($100K base / $100K variable) + Uncapped Commission

Over the last 90 days, our CEO and our Account Executive have booked nearly $1M in ARR through a combination of new customers and expansion within our existing customer base.

Our current AE is pacing toward $1.5M in new logo and cross-sell ARR this year.

To say this is an exciting time to join Whippy would be an understatement.

We're looking for a Founding Account Executive who is excited about joining early behind a fast-growing product and helping us build what comes next.

Why "Founding"?

You will be joining our solo Account Executive as we are building out our GTM motion. You will play a pivotal part in how we build and scale it.

There aren't layers of approvals or bureaucracy.

There is a great product, incredible momentum, and an opportunity to help finish building what our current AE started and shape it for whoever comes next.

We're looking for someone who wants to build not just sell.

Why now?

Four years ago, Whippy was a best-in-class SMS platform.

Today, we're an AI communications platform helping businesses automate customer conversations and operational workflows with messaging, VoIP, AI Agents, deep integrations, and our own workflow engine.

Customers like Your Employment Solutions and Staffworks have generated more than $1M in measurable value using Whippy.

We now serve more than 1,000 customers, have 30 engineers, and continue to expand what our platform can do every quarter.

Even more exciting, it's common to land a $50K ARR customer and expand that relationship by another $100K+ over time.

That's the kind of platform every great Account Executive wants to sell.

What makes this opportunity different?

You'll own the entire sales cycle from prospecting to close.

You'll build pipeline through outbound, referrals, existing customers, partners, conferences, and strategic relationships.

You'll work directly with our CEO every day, helping shape deals, strategy, and how we continue to scale our go-to-market organization.

You'll have direct access to our engineering team, giving you the ability to provide customer feedback, influence the product roadmap, and collaborate closely with the people building what you sell. At Whippy, customer feedback doesn't disappear into a ticketing system—it helps shape what gets built.

This is a remote role, but you'll need to work East Coast hours (roughly 8:00 a.m.–6:00 p.m. ET), since most of our prospects and customers are East Coast-based.

As we continue to grow, you'll have an outsized influence on how our sales organization evolves. The people who join early won't just help us close more business, they'll help define our sales culture, shape future hiring, improve our sales process, and build the foundation for the team that follows.

If you have a better idea, we expect you to speak up. Good ideas win here, regardless of title.

Who succeeds at Whippy?

People who are naturally entrepreneurial... the kind who've founded something themselves or treated their territory like they owned the business.

People who create opportunities instead of waiting for them.

People who are curious enough to understand technical products and disciplined enough to master consultative discovery.

People who build long-term customer relationships instead of simply closing transactions.

People who are excited by the idea of helping build a billion-dollar company, not just joining one after someone else already did the hard part.

This probably isn't for you if...

• You want every lead handed to you.

• You need every process documented before taking action.

• You prefer layers of management over ownership.

• You want to sell one simple product the exact same way every day.

• You need standard West Coast or flexible hours this role runs on East Coast time.

But if this sounds like you...

You want direct access to the founders.

You want to work shoulder-to-shoulder with engineering.

You want to sell a product customers genuinely love.

You want to influence the future of the company—not just your own quota.

You want to look back five years from now and say:

"I was one of the first sales hires at Whippy, and I helped build what it became."

Then we'd love to meet you.