A top salesperson loses an 18-month enterprise deal.

Then she walks into The Pitch room to sell a product that could have saved it.

One problem: she’s selling a sales intelligence tool… with zero sales.

This is Meghan Scanlon and Aleoop.

So when should you walk into the room — with the story, or with the stats?

#177 Aleoop: Show Me The Sales!

The Deal That Died—and the Company It Sparked

Meghan’s origin story hits anyone who’s ever carried a quota.

Big streaming company. CTO aligned. Contracts are circulating.

Then a “routine” scoping call surfaces six product gaps.

“By the end of the call, I’d uncovered six really fundamental product gaps preventing me from closing the opportunity,” Meghan said.

Worse: product, engineering, and leadership had no idea this had been happening for years.

Later, a colleague laughed, “I lost that same deal two years before you.”

Sales knew. Product didn’t.

Across B2B, roughly 30% of deals are lost to competitors, often due to avoidable product gaps.

Aleoop was built to make that visible — and quantifiable. 

Aleoop plugs into Gong, Slack, Salesforce, Jira. It listens for patterns in unstructured sales data, flags product gaps and the revenue opportunities they present.

The problem resonated immediately. Every investor in the room had lived it.

But the pushback was unavoidable, when investors discovered she only had customers using the product for free.

• “What’s preventing you from getting signed contracts today?” — Elizabeth Yin
  

• “Free is always scary.” — Mike Ma
  

• “Girl, you need to get paid. Right now.” — Laura Lucas
  

The optics weren’t great: a career salesperson building a sales-adjacent tool… without revenue.

Meghan’s explanation was simple—and risky.

“I wanted to make sure it worked first.”

The ML models launched in July. This was mid-August. She wasn’t selling certainty. She was selling conviction.

After The Pitch

Thirty days later, the first customer paid.

Then in the following months:

• Nine customers total
  

• Five paying
  

• $200K raised at a $4M valuation

It’s Not “When?” It’s “Why?”

The irony wasn’t lost: a data product pitched before it had data. But Meghan doesn’t regret pitching early.

“All worth it,” Meghan said in her follow up interview.

And she’s probably right, for her goal.

But here’s the real filter before you pitch:

• If you need capital → wait for proof. Validation is necessary.
  

• If you need feedback and access → going early can work.
  

• If one month materially changes your story → wait the month.

It’s all about what you’re optimizing for…  

Thirty days could be the gap between:

• A hopeful narrative
  

• And a credible ask

Lead with what investors can’t argue with.

Numbers. Sales.

That’s when the room stops debating your premise — and starts negotiating your price.

Join us for The Pitch Tampa!

April 21-23. Sunny Tampa, FL. Three days of live pitch filming, real conversations, and the kind of community you can only build in person.

We're bringing together the investors, founders, and listeners who make this show what it is. If you've ever wanted to see what actually happens behind the scenes—or if you just want to spend three days with exceptional people who are building the future—this is it.

This event is for:

• Investors looking to meet their next portfolio company

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You'll watch live pitch filming, connect with brilliant builders and investors, eat incredibly well (it's Tampa, after all), and be part of the community that's shaping the next wave of startups.

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