Inclusively’s ICP Surgery: What Happens When Your Entire Buyer Persona Changes Overnight

Imagine you’ve just closed your 50th enterprise customer. Salesforce, Accenture, and dozens of others are paying you. Your sales team knows exactly who to target: VP of Talent Acquisition, Chief Diversity Officer. Your pitch is dialed in. Your demos convert. Everything works.

Then you realize you need to build a completely different product for a completely different buyer.

In a recent episode of Category Visionaries, Charlotte Dales, CEO and Co-Founder of Inclusively—a workplace personalization platform that’s raised $20 million—described what happened when she pivoted from a hiring platform to a retention platform. The product changed. The value proposition changed. And most painfully, the entire ICP changed.

Here’s how she navigated the most dangerous pivot in B2B: changing who you sell to while keeping the customers you already have.

The ICP That Stopped Working

Inclusively launched in late 2020 as a hiring platform focused on disability inclusion. The ICP was straightforward and the timing seemed perfect.

“We started as a hiring platform, so the ICP was actually much easier. It was like a VP of Talent Acquisition and then we started at the end of 2020. So that was like in a very good moment for DEI and where a lot of investments were getting made. So it was usually the VP of Talent Acquisition and the Chief Diversity Officer,” Charlotte explains.

They executed well. The company grew to about 50 enterprise clients across different industries. The sales motion worked. The product delivered value. By conventional metrics, Inclusively was succeeding.

But by early 2023, Charlotte saw cracks forming in the foundation. “We started to see, okay, 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.”

This wasn’t just about market conditions—it was about building something that could last. Charlotte had learned from her first company: short-term tailwinds make for fragile businesses. She needed to find a more durable problem to solve.

The Bigger Problem That Changed Everything

The insight came from looking at who was actually entering the workforce and what was happening to them.

“Over 50% of people from Gen Z identify with having at least one learning difference, mental health or some sort of disability,” Charlotte notes. This wasn’t a hiring problem—it was a retention crisis. “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.”

Companies were successfully hiring diverse talent. But they were failing to retain them because their processes and support systems weren’t built for how this generation worked.

Charlotte saw the opportunity to solve a much bigger problem than hiring. The new product, called Retain, would help companies personalize their employee experience at scale. Instead of focusing on bringing people in, it would focus on keeping them productive and engaged once they were there.

But this shift brought a painful reality: “That has actually completely changed our icp, which in some ways is very good because it actually creates a more senior buyer, which helps with a lot of, you know, just sort of like the sales cycle. But it one meant that it wasn’t.”

She pauses, then delivers the hard truth: “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.”

The Catch-22 of Moving Upmarket

The new ICP wasn’t adjacent to the old one—it was completely different.

“Underneath the Chro, our product touches, you know, hr, technology, benefits, product services, their accommodations team. So we’ve actually kind of moved into like a more senior buyer set. But also there’s just a lot more people now that need to be involved,” Charlotte explains.

This is the ICP change paradox that kills companies: you’re moving upmarket to more senior buyers with bigger budgets and strategic importance. “So it’s like, you know, a catch 22.”

More senior buyers mean bigger deals, but they also mean:

• Longer sales cycles
• More stakeholders in the buying process
• More complex implementation requirements
• Different success metrics and ROI calculations

Charlotte had to completely rebuild her sales process while maintaining relationships with 50 existing customers who had bought a different product from different buyers.

The Existing Customer Problem

Here’s what makes an ICP change so dangerous: your existing customers aren’t just irrelevant to the new strategy—they’re actively complicated.

Charlotte had contracts with VPs of Talent Acquisition. Her new product sold to CHROs. These aren’t just different people—they’re often in different power structures with different priorities and budgets.

“We grew to about 50 enterprise companies. We worked with Salesforce, Accenture, all different, mostly large enterprises, but all different industries. It meant that it was really hard.”

The old playbook of “land and expand” didn’t work. You can’t just walk from the VP of Talent Acquisition into the CHRO’s office and say, “Hey, want to buy something totally different?”

Charlotte doesn’t detail exactly how she handled existing contracts in the interview, but the implication is clear: she had to essentially start over with new sales cycles at the same companies, treating them like fresh prospects for the new product rather than expansion opportunities.

Why Charlotte Chose This Anyway

Most founders would avoid an ICP change this radical. The smart play would be to find a way to expand the existing product to new buyers within the same category. Charlotte went the opposite direction and doesn’t regret it.

“But I think that the problem that we’re solving now actually has a lot more bottom line impact in a positive way for organizations. It solves an even bigger problem. It’s expanding Expanded our market size,” she explains.

This is the key insight: she optimized for strategic importance rather than sales efficiency. A longer sales cycle with a CHRO who has real budget authority and strategic mandates beats a faster cycle with a VP who needs three approvals for every decision.

The market size math also made sense. “And for the sake of, you know, accelerating our mission, we’re actually leveling the playing field for people with disabilities by normalizing this process for everyone.”

Instead of selling to companies that wanted to hire diverse talent (a subset of companies, dependent on market conditions), she was now selling to every company that needed to retain Gen Z workers (basically everyone, independent of market conditions).

The Speed That Saved It

What made this ICP change survivable wasn’t just the strategic logic—it was the execution speed.

Charlotte leveraged her existing enterprise relationships to validate and build the new product. “We interviewed them, we had them help us build this product,” she says, specifically calling out Salesforce as the first pilot customer.

This is the critical move that most founders miss when changing ICP: use your existing customers to de-risk the new direction, even if they’re not the ultimate buyers. Charlotte got Salesforce—a marquee name—to validate the new product concept and help build it.

“And I think when I talk to investor today about how the business is doing, you know, I’m like, you know, 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.”

Twelve months from insight to pilot with Salesforce. That speed created momentum that made the ICP change feel less like a desperate pivot and more like strategic evolution.

The DEI Transition Reality

Charlotte also had to navigate the broader market shift around DEI budgets and roles. “We’re seeing it in some instances more so with prospects than with our existing clients. Today we’re seeing it more with, you know, prospects that have been in pipeline and then that person is no longer there.”

This validates her decision to change ICP. If she’d stayed focused on Chief Diversity Officers as primary buyers, she’d be watching her ICP literally disappear from organization charts.

“We definitely have a completely different ICP than we started out with. We still have DEI involved where, you know, these companies still have their chief diversity officer and they really, I think a lot of the work we do helps, the data that we’re collecting actually helps inform their initiatives and get more buy in from the company. But we completely had to change icps from one product to the next.”

DEI leaders went from primary economic buyers to influencers and users. That’s a massive shift in how you position, sell, and deliver the product.

What This Actually Means for Founders

Charlotte’s experience reveals three hard truths about ICP changes:

First, adjacent pivots are fiction. You can’t gradually shift from one ICP to another if they’re in different parts of the org chart with different budgets. It’s a complete restart, not an expansion.

Second, existing customers can’t save you. The natural instinct is to leverage existing relationships to cross-sell the new product. But if the buyer is different, those relationships don’t transfer. You’re starting from zero.

Third, strategic importance beats sales efficiency. Charlotte chose a longer sales cycle with more stakeholders because the problem was more important to the business. She optimized for deal quality and durability, not velocity.

The question every founder facing an ICP change needs to answer: are you changing because your current ICP is dying, or because you found a better one? Charlotte had both—the DEI market was contracting and the retention market was bigger and more strategic.

That combination made the pain of starting over worth it. But it was still painful, still risky, and still required rebuilding everything from messaging to sales process to customer success.

The only thing that made it work was speed and commitment. Charlotte didn’t test the waters—she jumped in completely and moved fast enough that momentum carried her through the chaos.