EPISODE 260
Why Your Marketing Isn’t Working Anymore (and How to Fix It)
with Karen Hayward
What if the reason your marketing “isn’t working” these days isn’t your team — but your strategy?
In today’s environment, buyers are changing faster than most companies can keep up. Sales teams are frustrated. Leads are down. And what used to work suddenly doesn’t. The real issue? Most organizations are still operating with outdated assumptions about how to turn their prospects into customers.
In this episode, Rachel sits down with Karen Hayward, Managing Partner & CMO at Chief Outsiders and author of Stop Random Acts of Marketing, to unpack what modern growth really requires — and why CEOs must reclaim ownership of it.
Karen brings more than 20 years of experience advising Fortune 1,000 and mid-market companies. At Chief Outsiders, she leads a team of 40-plus CMOs and CSOs, helping organizations align sales and marketing around the voice of the customer to accelerate revenue. She’s a Vistage and TEC-certified speaker, guest lecturer, and trusted advisor to CEOs and private equity leaders ready to build growth engines in today’s marketplace.
In this episode, Karen breaks down how to replace marketing chaos with a disciplined strategy.
The Modern Buyer Has Changed — Has Your Strategy?
Today’s landscape paints a generationally different picture of consumer behavior than the one many of us grew up with.
Nearly 65% of B2B buyers are now Millennials or Gen Z. They research independently. They distrust early sales engagement. They want rep-free or digital-first buying experiences. And increasingly, they’re discovering companies through AI platforms.
If your growth engine still relies on cold outreach and traditional sales funnels, you’re misaligned with how today’s customers actually want to buy.
Karen explains that marketing now owns the majority of the funnel.
Her advice? Start with the voice of the customer. Interview recent wins and losses. Identify what customers truly value — not what you assume they value. Then align positioning, messaging, and sales enablement around that insight.
From Random Acts to Real Results
One of the most common mistakes Karen sees? Companies executing disconnected tactics without a cohesive strategy.
Instead, she urges leaders to focus on three foundational pillars:
- Deep customer insight
- Clear competitive positioning
- Honest understanding of company strengths
Only then should you invest in acquisition.
Karen also shares tactical wins leaders can implement immediately:
- Record discovery calls and use AI to tighten proposal alignment
- Run an AEO grader report to evaluate how AI platforms see your business
- Build robust FAQ content based on real buyer questions
The throughline? Discipline over randomness.
Marketing remains full of engagement metrics and busy dashboards, but true success relies on measurable growth.
Enjoy this episode with Karen Hayward…
Soundbytes
09:21 – 09:32
“About 65%-plus of B2B buyers today are millennial or Gen Z. And they buy drastically differently than baby boomers do.”
37:46 – 38:30
“By the time the salesperson gets engaged, you have very little time to build trust. So how do you coach yourself to get better on the at-bats that you have given how little time you have? So the one thing I would do with the sales team, or with BD people, or with founders, or with you — if you’re talking to clients — is I would record the initial conversation with the client and understand what their needs are. I would record that. And then I would send a follow-up email to them with a summary of what they said, and I’d ask them to correct me.”
Quotes
“Marketing now owns most of the sales and marketing funnel.”
“Stop doing random acts of marketing and hoping something works.”
“You can’t rely on your sales force to tell you why you’re winning and losing.”
“Open the door and ask about them first.”
“Engagement doesn’t pay payroll.”
Links mentioned in this episode:
Connect with our Guest Host
Website: https://www.chiefoutsiders.com/profile/karen-hayward
Phone: 650-823-4292
Connect with Karen Hayward on LinkedIn:
https://www.linkedin.com/in/karenhaywardcmo/
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