The Dark Funnel Future: Insights from Kaylee Edmondson, Senior Director of Demand Gen at Chili Piper

It’s difficult to embrace the unknown—uncertainty doesn’t come easily to Ops leaders. We want hard facts and accurate data to inform trackable activities and results we can anticipate. When I sat down with Kaylee Edmondson—the Senior Director of Demand Gen at Chili Piper—we talked about how the funnel as we know it is gone. The future is dark.

Kaylee Edmondson is a podcasting and marketing savant for whom change is a welcome challenge. As the Senior Director of Demand Generation at Chili Piper and host of the popular podcast, Demand Gen Chat, Kaylee offers her honest and straightforward wisdom on the shifting grounds of data, B2B marketing, and no-bullshit leadership.

She’s growing her team at Chili Piper—an inbound conversion platform that helps marketers optimize their website conversions—as they expand the boundaries of what we expect from demand generation. I sat down with Kaylee to discuss why she believes embracing the unknown is where the future of B2B marketing is found.

This interview has been edited for brevity.

Nick Bonfiglio: Your journey to Chili Piper is unique, how did you get here?

Kaylee: In my first B2B SaaS role, I was the 20th employee at a small startup in Nashville. I was manually routing leads. Picture this—a new lead would enter our HubSpot. I would unplug my laptop, run over to the sales floor, and shout, “Who’s available right now?” When I got pregnant, I realized I couldn’t run around like that anymore! That was how I discovered Chili Piper—as a customer. I implemented it and it solved all of our problems.

A couple of years later, a recruiter reached out and described this awesome company to me. I told them, “If this is Chili Piper, I’m down. If it’s not, I’m not looking right now.” He was befuddled that I had guessed correctly. I was hired shortly after. It’s a wild story—to go from championing a product at another B2B company to owning that company’s demand gen strategy.

You’re also the host of the podcast, Demand Gen Chat. Tell me about how that came to be.

I’m obsessed with podcasts. I realized a few years ago that there wasn’t a podcast community for demand gen marketers. Demand Gen Chat started as a passion project to cover some of these high-level topics that weren’t being discussed. I chat with leaders in the space to find out more about their strategies to drive revenue. We talk about the experiments they’re doing, their failures, and their successes. My goal is to give people practical insights they can take back to their demand gen teams and use right away.

It’s been wildly successful—we have 7,600 listeners after only 2 years. Now, we’re looking for ways to cultivate an engaged community and provide them with more content that’s helpful in their day-to-day life, like leadership advice and industry benchmarking.

What is the importance of data to demand gen? How are things changing?

In the past, every single ad campaign—down to the keyword—was all about data. Now that we know cookies are on the way out, we’re seeing a shift towards dark funnel activities—those that can’t be tied directly to the bottom line or measured in Salesforce. The CFOs of the past would say, “If we don’t see it in Salesforce, it didn’t happen.”

My new way of thinking is that we’re using these activities to lead our marketing strategy and innovate new ways of reaching our customers. A perfect example is our podcast, Demand Gen Chat. The most important markers of success—recurring listeners and community-building—can’t be measured in Salesforce. But we’re building a strong community around the podcast that will reap returns. We’re pushing ourselves out of our comfort zone, but it’s also opening up new possibilities.

Nick: What’s your advice to leaders going through this change?

I know it’s intimidating—gut-based marketing is scary. But I’m convinced that those who ditch cookies altogether and lean into marketing without a million tracking pixels will ultimately shine in the long run—they won’t be dependent on the old guards of the past.

There’s a company I’ve been following that adopted a ‘no tracking’ approach already. They know their customer’s journey is complex, so they’re devoting their time to dark funnel activities like podcasting, offline channels, organic social media reach, and influencer marketing.

A word of advice—that I need to follow myself—the faster you lean in and move towards that model, the better off you’ll be. It will require an assessment of the risks involved and a great deal of trust in your demand gen and marketing leaders. But in the end, you’ll be light-years ahead of your competitors.

The Dark Funnel Future: Gut-Based Marketing

What’s a data nightmare you’ve experienced?

I’m going to be vulnerable. My first opportunity to represent the marketing team to our board was last quarter. I was nervous. Our sales leader presented before me and his numbers directly contradicted the numbers on my slide. I realized immediately that we didn’t go over our slides together, otherwise, we would have realized we didn’t pull our data the same way.

Our board of brilliant people listened to him and then me—exactly as planned—and they were rightfully confused. I interpreted the marketing numbers one way, our sales guy interpreted them another. Our overall objectives were the same but the stories were polar opposites. Luckily, our CEO stepped in and said just that. But I feel like if that oversight wasn’t addressed, all trust would have been lost.

It’s a common data problem, which is why Syncari created a solution built around it. The lesson? Check your numbers before you go to the board meeting and do a dress rehearsal. My nightmare was completely preventable, so don’t let it be yours.

Do you have a leadership tip for operations folks?

I have to know and understand your personal life and your values to work well with you. It connects us on a human level. In a remote world, that connection is difficult to create. So our team implemented an onboarding resource called ‘read me’s.’ Everyone on our team writes about themselves—as an individual and as a demand gen leader. We write our entire philosophy—how I run my team, how I prefer feedback, and how I work. It’s meant to be blunt and crystal clear because this is our opportunity to share our preferences and expectations.

It has created great synergies because we move past the nonsense quickly. We learn how to work together without going through the process of misreading or misinterpreting communication styles. As our team grows quickly, ‘read me’s’ have been instrumental in getting to know one another and working together effectively.

Finally, what’s exciting to you about the future of demand gen?

B2B marketing is finally taking a page out of the B2C marketing playbook. We’re no longer putting content behind lead forms or SEO-laden blogs, we’re creating rich and informative resources people seek out. Chili Piper used to gatekeep content too—we’re no stranger to the old ways. Podcasting is a huge part of our new playbook of progressive marketing strategies.

On the other hand, I think B2B SaaS marketing will always be a battle of features. Who can build the best features, the fastest? Feature battles may be won and lost, but the companies that will win the war are those with strong branding—the ones who have taken the time to build the community around them. We’ve accepted that challenge, it’s just a matter of who will rise up to meet us.

Want to learn more from Kaylee? Follow her on LinkedIn and listen to Demand Gen Chat.

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