The Story of Inclusively: From an Unannounced Flight to American Express to Building the Future of Workplace Personalization

The Story of Inclusively: From an Unannounced Flight to American Express to Building the Future of Workplace Personalization

The deal was dead. After months of diligence, legal fees, and sleepless nights, American Express had pulled the acquisition of Charlotte Dales’ first company. She had two choices: accept defeat and liquidate, or do something drastic.

She got on a plane.

In a recent episode of Category Visionaries, Charlotte Dales, CEO and Co-Founder of Inclusively—a workplace personalization platform that’s raised $20 million—shared the story of how a moment of desperation at her first company shaped everything about how she built her second. It’s a story about trusting your instincts, knowing when to pivot, and recognizing that the best founders don’t just build products—they build their way out of impossible situations.

The Flight That Changed Everything

It was 2017. Charlotte and her Co-Founder had spent four years building a mobile payments app for restaurants and bars in London. They’d grown to 200 locations. American Express wanted to buy them. Then, right before closing, the buyer called to pull the deal.

“She knew how much it meant to us to sell this company. And you know, that we had paid, you know, so much money and lawyers and everything, you know, were basically doing this. We were putting everything into doing this transaction,” Charlotte recalls. The advice from her board and M&A advisor was grim: consider liquidation.

Charlotte’s response was immediate. “I just said, you know, they were kind of like, you know, talking about just going into liquidation and all these options. And I was like, that’s just not happening. I’m going to New York. If someone wants to come with me, they’re welcome to come.”

The strategy was calculated. “This was kind of back when you didn’t really have WI fi on airplanes. And so at 9:00am London time, I was on the plane, sent the text as were taking off to my point of contact there and said, I’m on my way to New York from London and I’ll land at 1pm and I’ll come by the office.”

Then she went dark for eight hours. “I strategically did it because I was like, you know what? They’re going to know I don’t have Wi Fi, so they’re not going to be able to tell me not to come. Like, I didn’t give them enough time to redirect me.”

When she landed, American Express had scrambled to get the right people in the room. Charlotte found herself writing her pitch on a whiteboard for the President of the Consumer Group—someone who hadn’t even been involved in the original deal because it was too small. They asked about one specific piece of functionality. She said yes. “And so went back to London and we built what they needed within a weekend and got through the diligence and closed the deal.”

When asked if the deal would have happened without that flight, Charlotte doesn’t hesitate: “100,000%.”

The Hard Lessons That Shaped What Came Next

Charlotte walked away from that exit with more than a successful acquisition—she walked away with hard-earned lessons about what not to do next time.

The biggest lesson was about choosing investors. “I feel like my Co-Founder and I, my first company, we literally felt like it was all on us. Like when were running out of money, we would throw all of our savings in to the company,” she explains. “And you know, if the board gets used to you always saving the company at your own personal expense. Expense, you’re giving them, like, the best of both worlds.”

It wasn’t sustainable. “I think that was a huge learning. It’s just, you know, it’s not just me. Like, you are all our investors. You are on the board. You have fiduciaries along with me.”

The second lesson was about instinct. “I just am a big believer that where there’s a will, there’s a way, and there’s always a way out. Like, you are a smart person. You started a company,” Charlotte says. “And I feel like in Any situation in my first company, and even now, whenever I’ve not listened to my instinct, it’s always, you know, led me really far away from where we need to be.”

But the third lesson was about knowing when not to rush. “You can be more patient, especially at the beginning, about who you partner with, because you don’t have this huge burn, you don’t have all these employees yet, but you’re so excited to start your business that you feel like you’re in this big rush.”

Charlotte learned this one the hard way with Inclusively. “I just was so excited to start my second company that I dove headfirst into sort of the wrong situation because it was the situation I felt like would get me to, like, start the business faster.”

The Personal Spark That Became a Company

The idea for Inclusively came from an unexpected place: watching Charlotte’s cousin work. “My cousin became the first licensed facialist in the state of Florida with Down syndrome. And I went to go see her work for the first time. And I just noticed how easy it was for her employer to make some slight adjustments to her working environment.”

Charlotte saw the disconnect immediately. Small accommodations made massive differences in productivity and job success. But enterprises had no scalable way to do this. “So wanted to figure out how can we leverage technology to make it really, really easy for large enterprises to do this at scale without disrupting their operations and, you know, without the perception that it’s going to be so hard.”

Inclusively launched in late 2020 as a hiring platform. The product allowed candidates to share what accommodations they needed—both for interviews and on the job—and connected them with employers. The timing seemed perfect. DEI investments were surging. Charlotte quickly signed enterprise clients including Salesforce and Accenture. They grew to about 50 enterprise companies.

Then the market shifted.

The Pivot That Redefined Everything

By early 2023, Charlotte saw the warning signs everywhere. “The hiring market is turbulent, the DEI market is turbulent. And we need to figure out how we can actually make a sustainable impact over time that’s not reliant on strategies that will ebb and flow.”

But the real insight came from looking at who was actually entering the workforce. “Over 50% of people from Gen Z identify with having at least one learning difference, mental health or some sort of disability. And we’re already seeing the ramifications that companies processes aren’t set up. There’s 30% of people who are Gen Z get fired or leave within the first 90 days.”

This wasn’t a hiring problem—it was a retention problem. Companies needed to support this generation differently. Charlotte and her Co-Founder built a new product called Retain. Instead of focusing on hiring, it allowed any employee to anonymously share what they were going through—ADHD, caregiving responsibilities, divorce, anything—and instantly see relevant company resources.

“We can deduce what pain points have we identified. And then we serve up all the company’s existing products, benefits, services, technologies, policies, everything that usually is spread across a million different platforms at a company, and it’s hard to access,” Charlotte explains.

The pivot brought new challenges. Their entire ICP changed. “We couldn’t just jump from our, you know, contract we had with them today to selling our new product. Cause it was a totally different buyer,” she admits. Instead of VPs of Talent Acquisition, they were now selling to CHROs and heads of HR technology.

But Charlotte moved fast. “We saw this coming, built a product, got Salesforce to launch it, like all within 12 months. And we’re like, very proud of that.” She didn’t build in isolation—she brought existing customers along. “We interviewed them, we had them help us build this product.”

Building the Future of Work

Today, Charlotte describes Inclusively as creating an entirely new category. “It’s around how do you customize and make your employee experience personalized to the same level that you care about it for your customers? And I think that it’s a very new way of thinking about employee experience.”

The platform solves what Charlotte sees as a fundamental mismatch between how companies operate and what the next generation of workers needs. “They didn’t just wake up this way. They grew up in an education system where they were diagnosed way earlier and way more frequently. And they grew accustomed to advocating for accommodations in the education system. And they’re just placing those demands on the workforce.”

Looking ahead three to five years, Charlotte’s vision is clear: strategic partnerships at scale. “Our big focus for this coming year is around channel partnerships and strategic partnerships,” she shares. “I think next three to five years I want to have two to three really strong partners that are way bigger than us in the industry that we’ve aligned to and are sort of co selling together.”

The rationale is pragmatic. “The enterprise sales cycle can be a slog. It’s slow, it’s complex, there’s lots of people involved.” Rather than fight that reality, Charlotte wants to leverage it through partners who already have the relationships and trust with her target buyers.

It’s a fitting strategy for a founder who’s spent her career finding creative ways around obstacles rather than battering through them. From that unannounced flight to New York to the rapid product pivot, Charlotte’s superpower isn’t just execution—it’s recognizing when the conventional path won’t work and building a better one.

The question she’s asking herself now: “What is the ICP of our strategic partnerships because those can sell so much faster for us than our sort of one off, one to one sales.”

If history is any guide, she’ll figure it out. And if she doesn’t, she’ll get on a plane.