Inclusively’s $0 to $20M Playbook: Why Charlotte Dales Fired All Her Demand Gen Tactics in 2024

Your cold emails are going to spam. Your HubSpot tracking is triggering enterprise filters. Your BDRs are burning through call lists with nothing to show for it. And that webinar you spent three weeks promoting? Twelve people registered, three showed up.

Welcome to enterprise marketing in 2024, where every playbook from 2020 is dead.

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 the moment she realized her entire marketing operation had become worthless. Then she explained what she built to replace it, a strategy that tripled weekly meeting rates and forced her team to turn off lead generation because they couldn’t handle the volume.

The Great Enterprise Marketing Die-Off

Charlotte’s team had done everything right. Or at least, everything the playbooks said to do.

“We have done demand gen, we have done webinars, we’ve done all the things BDRs, tried to do, cold calling, all the stuff,” she explains. They’d built a proper demand gen engine. They’d hired BDRs for cold outreach. They’d invested in content marketing. They’d done it all.

None of it was working.

The problem wasn’t execution—it was that the entire ecosystem had fundamentally changed. “There are spam filters on every enterprise account. If you’re like attaching HubSpot tracking and stuff, it’ll just automatically decline,” Charlotte points out. The technical infrastructure of enterprise companies had evolved to block exactly the tactics that used to work.

But the bigger shift was human, not technical. “We’re just all inundated with emails all the time from randoms and strangers that like you don’t read them anymore and I don’t read them anymore,” she says. Everyone had learned to ignore cold outreach because everyone was doing cold outreach.

Charlotte had seen the shift firsthand. “When we first started, like I almost got a response on every cold email I sent. And I was sending emails to CEOs of these companies just like, hey, I want to tell you what I’m doing. We get a response.”

That world was gone. “But now that everyone’s sort of able to flood people’s inboxes, 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 team faced a choice: optimize tactics that were fundamentally broken, or build something completely different.

The Demand Gen Trap

Before we get to what Charlotte built, it’s worth understanding why she couldn’t just “fix” demand gen.

“Demand gen is amazing, but it really needs to come once you’re kind of foot like off the ground a bit more where you can have that wait for like, you know, pieces of content dripping out and waiting for those leads to come through. And you’ve built up enough pipeline that it kind of services you,” she explains.

This is the catch-22 of enterprise demand gen: it works great when you don’t need it. When you already have pipeline, when you already have brand awareness, when you can afford to wait three to six months for content to compound—that’s when demand gen becomes a reliable channel.

But when you’re early, when you need meetings this quarter, when your pipeline is thin? Demand gen becomes a slow-motion failure that burns cash while you wait for it to “work.”

Charlotte needed something that worked now, with the customers and resources she had today.

The Investor Network Framework

The solution came from looking at what she actually had: 60 investors.

“I actually went to all of my investors and we have about 60 investors,” Charlotte explains. But that’s where most founders stop—they ask investors for help, get vague promises, and nothing happens.

Charlotte built a system instead.

First, she got LinkedIn Sales Navigator. Then she loaded in all 60 investors and began systematically curating 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.”

This is the first critical insight: LinkedIn connections aren’t relationships. Most investors have thousands of connections but meaningful relationships with maybe a few hundred. Charlotte’s job was to identify which connections were actually relationships.

But here’s where the system gets powerful. Charlotte didn’t just ask for introductions—she manufactured them completely.

“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.”

Read that again. Charlotte’s team:

1. Identified the target prospects from each investor’s network
2. Researched each prospect individually
3. Wrote personalized emails for each one
4. Sent those emails to the investor
5. Had the investor forward them with a brief cover note

The investor’s job was to hit “forward” and add two sentences. That’s it.

The Results That Changed Everything

The impact was immediate and dramatic. “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.”

But it wasn’t just volume—it was quality. “We’re getting higher quality introductions with way more senior people,” Charlotte notes. Instead of fighting to get a 15-minute call with a VP of Talent Acquisition, she was getting introduced directly to CHROs who took the meeting because a trusted investor made the intro.

The conversion rate wasn’t 2% like cold email—it was north of 50%. Because these weren’t cold prospects; they were warm leads with built-in credibility from a mutual connection.

Charlotte didn’t stop with investors either. “I even get like my clients to do it. Like once we’re close with sort of a client or, you know, I’ll say like, hey, do you have any other chros that you know that would be interested in this?”

The framework was repeatable with anyone who had a network: investors, customers, advisors, even podcast hosts. “So we kind of just keep spreading it outside of just our investor group.”

Why This Works When Everything Else Dies

The investor network strategy succeeds because it solves the fundamental problem that killed traditional tactics: trust.

Cold email died because there’s no trust. The recipient doesn’t know you, doesn’t trust you, and has learned to ignore messages from strangers. Spam filters are just codifying what humans already decided.

But when an investor or customer makes an introduction, they’re transferring trust. The prospect takes the meeting not because of your email copy, but because someone they trust vouched for you.

This isn’t scalable in the traditional sense—you can’t send 10,000 investor intros per month. But Charlotte wasn’t optimizing for volume. She was optimizing for conversion and deal quality. “Those two things have completely driven our top of funnel strategy. And honestly, we’ve pretty much turned off everything else.”

The Tactical Implementation

For founders reading this thinking “I should try that,” here’s what Charlotte’s system actually requires:

Infrastructure:

• LinkedIn Sales Navigator subscription
• Investor list with LinkedIn profiles
• Clear ICP definition
• Team capacity to write personalized emails

Process:

1. Export investor connections monthly
2. Filter against ICP criteria
3. Book 15-minute investor calls
4. Get confirmation on actual relationships
5. Research each prospect (company, role, potential pain points)
6. Write personalized email for each target
7. Send batch to investor with instructions
8. Track forwards and follow up

Team: Charlotte mentions “people who write the personalized emails”—this isn’t a one-person job. You need researchers to qualify prospects and writers to personalize messages. But it’s still more efficient than a team of BDRs making cold calls.

The Uncomfortable Truth

Charlotte’s success reveals an uncomfortable truth about enterprise marketing in 2024: the channels that scale don’t work, and the channels that work don’t scale.

You can blast 10,000 cold emails, but you’ll get 2% response rates and terrible quality. Or you can methodically work through 60 investor networks, write 100 personalized emails per month, and triple your meeting rate with senior buyers.

Most founders will choose to blast. They’ll optimize subject lines, A/B test templates, and celebrate when they get response rates to 3%. They’ll keep doing what’s “scalable” even as it fails.

Charlotte chose the opposite. She built a system that required more work per prospect but generated dramatically better results. “And I think that strategy, alongside the fact that we are just showing up in person to our events, to other people’s events, and really making connections and hosting like dinners before a big conference the next day where we know a lot of people will be there, those two things have completely driven our top of funnel strategy.”

The future of enterprise marketing isn’t automation and scale. It’s relationship-driven, high-touch, and built on transferred trust. Charlotte just proved it works better than everything we’ve been told to do.