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Highlights
When Enterprise Sales Are Dead, Show Up Unannounced
Getting on a plane to New York with no Wi-Fi and sending a text to American Express executives that you’re coming to their office unannounced might seem crazy. But for Charlotte Dales, it saved her first startup’s acquisition.
In a recent episode of Category Visionaries, Charlotte, now CEO of Inclusively, shared how that bold move in 2017 became the foundation for her approach to enterprise sales: when conventional methods fail, create your own playbook.
The Death of Traditional Enterprise Marketing
After raising $20M for Inclusively, a workplace personalization platform, Charlotte discovered that enterprise sales tactics that worked just two years ago have become virtually useless.
“We have tried everything under the sun,” she explains. “We have done demand gen, we have done webinars, we’ve done all the things – BDRs, tried to do cold calling, all the stuff.”
The problem? “There are spam filters on every enterprise account. If you’re 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 you don’t read them anymore.”
Building a New Enterprise GTM Engine
Instead of doubling down on dying tactics, Inclusively completely reinvented their approach. They systematically mapped their 60 investors’ LinkedIn networks to their ideal customer profile, pre-wrote personalized emails, and orchestrated warm introductions.
The results were immediate: “We tripled our weekly meeting rates,” Charlotte reveals. The program became so successful they had to temporarily pause it because they couldn’t handle the meeting volume.
The Pivot That Changed Everything
But getting meetings was only part of the challenge. By early 2023, market signals forced Inclusively to confront an uncomfortable truth: their initial product strategy wasn’t sustainable.
“The hiring market is turbulent, the DEI market is turbulent,” Charlotte recalls. “We needed to figure out how we can actually make a sustainable impact over time that’s not reliant on strategies that will ebb and flow.”
The data pointed to a larger opportunity. Over 50% of Gen Z workers identify with having a learning difference, mental health condition, or disability. More concerning, “30% of people who are Gen Z get fired or leave within the first 90 days.”
Within 12 months, Inclusively completely rebuilt their product with Salesforce as their first design partner. The new platform, Retain, allows employees to anonymously share their needs and connects them with relevant company resources.
This pivot created a new challenge: their entire GTM motion was built around selling to VPs of Talent Acquisition and Chief Diversity Officers. The new product required reaching the CHRO and an entirely different buyer set.
Marketing Through Service
Rather than treating marketing as a separate function, Inclusively embedded it within their service delivery team. “Anything we learn from a customer perspective is going into marketing within the same day,” Charlotte explains.
This structure ensures marketing messages directly reflect customer realities rather than theoretical value propositions. When they developed new messaging around workforce demographic shifts, “within a month that whole story was covered by Forbes.”
The Road Ahead
Looking forward, Inclusively is focused on strategic partnerships to accelerate enterprise adoption. “Our big focus is around channel partnerships… 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.”
For founders navigating enterprise sales today, Charlotte’s journey offers a crucial lesson: when conventional tactics stop working, don’t be afraid to rewrite the rules. Sometimes that means getting on a plane unannounced. Other times it means completely reinventing how you reach and serve customers.
The key is staying focused on fundamental market shifts rather than temporary trends. As Charlotte puts it, “Where there’s a will, there’s a way… If your product isn’t perfectly aligned to what the market needs, you pivot.”
Actionable
Takeaways
Choose your investors and board strategically:
Charlotte learned the importance of building a supportive board that acts as true partners. As she noted, "You really need to find people who want to be on a team with you when it comes to a board and investors and in the trenches." Founders should carefully evaluate potential investors beyond just capital, looking for those who will provide meaningful support during challenging times.
Trust your instincts on pivots:
When market conditions change, founders need to be willing to evolve their product strategy. Charlotte explained, "Where there's a will, there's a way... If your product isn't perfectly aligned to what the market needs, you pivot." The key is balancing quick decisions in urgent situations while taking time for careful consideration when possible.
Rethink traditional enterprise marketing:
Cold outreach and demand generation may not be effective for enterprise sales in today's environment. Inclusively found success by systematically leveraging investor and customer networks, with Charlotte sharing, "We tripled our weekly meeting rates" after implementing a structured approach to warm introductions through investors.
Build product with enterprise design partners:
When pivoting their product strategy, Inclusively worked closely with Salesforce as their first pilot customer. Charlotte emphasized the value of "interviewing them, having them help us build this product" to ensure market fit. Founders should seek out and deeply engage with marquee customers who can help shape and validate new solutions.
Align marketing with customer success:
For enterprise companies, Charlotte recommends closely integrating marketing with the teams delivering customer value. This ensures marketing messages reflect real customer needs and wins, noting "Anything we learn from a customer perspective is going into marketing within the same day."
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