7 Go-to-Market Lessons from a Founder Who Tripled Meeting Rates After Everything Stopped Working

7 Go-to-Market Lessons from a Founder Who Tripled Meeting Rates After Everything Stopped Working

Charlotte Dales had a problem. Every enterprise sales playbook she’d studied, every demand gen tactic she’d deployed, every cold email sequence she’d perfected—all of it stopped working in 2024. In a recent episode of Category Visionaries, the CEO and Co-Founder of Inclusively shared how she navigated multiple pivots, a complete ICP overhaul, and the death of traditional enterprise marketing to build a $20 million workplace personalization platform.

Here are seven hard-won lessons from her journey that every B2B founder needs to understand.

Lesson 1: Make It Stupidly Easy for Investors to Help You

Most founders ask investors for introductions wrong. They send vague emails asking for “help” or “connections to HR leaders.” Charlotte found a better way.

“I actually went to all of my investors and we have about 60 investors,” she explains. Using LinkedIn Sales Navigator, she loaded all 60 investors and curated their connections against her ICP. “I would say, hey, can I have a quick 15 minutes with you? Because obviously you don’t know everyone that you’re connected to on LinkedIn. And I said, who of this list of 100 people do you actually know and will you make an intro to.”

But here’s the critical part most founders miss: she didn’t stop at asking. “We have people who write the personalized emails for each person, send them all separately, send the investor the email addresses, and then they just forwarded on with a cover letter that we’ve written.”

The results? “We tripled our weekly meeting rates within starting that. And actually to turn it off for a while because we didn’t have enough to time to take all the meetings.”

The underlying principle: your investors want to help, but you have to remove every obstacle. Do the research, write the email, make it one-click easy. Your job is to manufacture introductions, not just ask for them.

Lesson 2: Recognize When Your Entire Category Is Shifting Beneath You

Inclusively launched in late 2020 as a hiring platform focused on disability inclusion. “That was like in a very good moment for DEI and where a lot of investments were getting made,” Charlotte notes. Their ICP was clear: VP of Talent Acquisition and Chief Diversity Officer.

Then the ground shifted. By early 2023, Charlotte saw the writing on the wall. “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.”

Instead of optimizing around the edges, she made a hard call: pivot the entire product. The new platform, Retain, solved a bigger problem—helping companies adapt to a workforce where “over 50% of people from Gen Z identify with having at least one learning difference, mental health or some sort of disability.”

The lesson isn’t about pivoting when things get hard. It’s about recognizing when your category’s foundation is crumbling and moving before you’re forced to.

Lesson 3: Speed Beats Perfection When Validating a Pivot

Once Charlotte decided to pivot, she 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.”

How? She leveraged her existing enterprise relationships. “We interviewed them, we had them help us build this product.” Rather than disappearing to build in isolation, she co-created with customers who already trusted her.

This approach served double duty: it validated product-market fit while simultaneously creating proof points for sales. When talking to investors or prospects, Charlotte leads with “we got Salesforce to be the first pilot.”

The principle: when you have existing customer relationships, weaponize them for validation. Your best product roadmap lives in conversations with customers who will actually pay for what you build.

Lesson 4: Your ICP Change Might Be Your Best Business Decision

The pivot from hiring to retention brought a problem most founders dread. “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,” Charlotte admits.

Her new buyer was more senior—reporting directly to the CHRO and touching HR technology, benefits, and accommodations teams. “So it’s like, you know, a catch 22.” Longer sales cycles, more stakeholders, more complexity.

But Charlotte doesn’t regret it. “The problem that we’re solving now actually has a lot more bottom line impact in a positive way for organizations.” The new ICP meant bigger deals with more strategic value, even if they took longer to close.

The lesson: don’t optimize for sales cycle speed. Optimize for strategic importance to the buyer. A 12-month cycle with the CHRO beats a 3-month cycle with a VP who has no budget authority.

Lesson 5: When Traditional Tactics Die, Don’t Do Them Harder

By early 2024, Charlotte’s team had exhausted the playbook. “We have done demand gen, we have done webinars, we’ve done all the things BDRs, tried to do, cold calling, all the stuff.”

None of it worked anymore. “There are spam filters on every enterprise account. If you’re like attaching HubSpot tracking and stuff, it’ll just automatically decline. And also we’re just all inundated with emails all the time from randoms and strangers that like you don’t read them anymore.”

The old Charlotte had better luck. “When we first started, like I almost got a response on every cold email I sent.” She was reaching CEOs directly. But that playbook died, and she recognized it. “At the beginning of this year were like, this isn’t working. Like we’re not getting any type of conversion. We’re spinning our wheels.”

The principle: when a channel stops working, the answer isn’t more volume or better copy. It’s abandoning the channel entirely and finding where real conversations still happen—like warm introductions from trusted sources.

Lesson 6: Tie Early-Stage Marketing Directly to Customer Delivery

Charlotte made an unusual organizational choice: her VP of Marketing reports into the service and delivery leader who manages both marketing and client-facing content.

“I think tying marketing in the early stages to part of the organization that’s actually delivering value for clients has been really helpful because those messages get so synced up,” she explains. “Anything we learn from a customer perspective is like going into marketing within the same day.”

The speed of this feedback loop shows in results. “We came up with this new messaging around, you know, tying the macro trends to what we’re doing and really seeing like, oh my gosh, that’s like really helping people to understand what we do, the problems we solve. And you know, within a month that whole story was covered by Forbes.”

The lesson: in early-stage companies, marketing shouldn’t be isolated from delivery. The best messaging comes from daily customer conversations, not keyword research or competitive analysis.

Lesson 7: Your Endgame Should Change Your Next Move

Looking ahead, Charlotte sees channel partnerships as her primary growth lever. “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 simple: enterprise sales cycles are brutal. “It’s slow, it’s complex, there’s lots of people involved.” Rather than fight that reality by optimizing sales process, Charlotte wants to leverage bigger organizations’ existing relationships.

This isn’t a “nice to have” strategy—it’s reshaping how she thinks about product development and positioning. The question keeping her up: “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.”

The principle: your three-year strategy should inform your quarterly tactics. If channel partnerships are the endgame, you should be building partnership-friendly infrastructure today, not scrambling to retrofit it later.

The Through-Line

What ties these lessons together isn’t tactical execution—it’s Charlotte’s willingness to constantly question whether her current approach still works. She pivoted products when the category shifted. She abandoned marketing tactics when they stopped performing. She completely changed her ICP when a bigger problem emerged.

But she didn’t thrash. Each pivot was deliberate, validated with customers, and executed with speed. That combination—clear-eyed assessment plus rapid execution—is what separates founders who navigate market shifts from those who get buried by them.

For B2B founders watching enterprise playbooks crumble in real-time, Charlotte’s journey offers a blueprint: move fast, stay close to customers, make it easy for others to help you, and never fall in love with tactics that stop working.