Interview: How Headway Grew Into a Thought Leader by Betting on Community, Content, and Focused Experimentation
Behind the Agency Podcast with Jacob Miller, Marketing & Brand Manager at Headway
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Prefer to skim? Below you’ll find key takeaways, quotes, and a blog-style breakdown of the episode.
TL;DR – Key Takeaways
Community first, sales second: Headway didn’t start with a growth hack—they started with a local founder meetup. That DNA shaped how they market and show up today.
Niche positioning can unlock warm intros: Their logistics-focused spinoff, Intermode, became easier to refer just by being industry-specific.
Content that teaches wins: Educational videos and articles—based on real project challenges—led to Fortune 500 clients.
YouTube is a long game: Their most valuable leads watched content for years before reaching out.
Referrals deserve real rewards: Headway thanks referrers financially, not with swag. They’re working to formalize this with a dashboard.
They’re building toward more than just client work: Long-term plays include education, recruiting, and philanthropy—all tied to a bigger BHAG.
Meet the Guest
Jacob Miller is the Brand & Marketing Manager at Headway, a dev agency known for its deep investment in community, thought leadership, and honest experimentation. He’s also deeply involved with Startup Wisconsin and has helped grow Headway’s content and reputation over the past eight years.
Episode Summary: What We Talked About
1. The Origin of Headway
Jacob walks us through how Headway started: four founders frustrated with the freelance grind who decided to build a better agency. Their secret? Community meetups came before marketing.
2. Why Their Best Work Became a Spinoff
Intermode wasn’t just a rebrand—it was a strategic decision to double down on a vertical where they already had traction: logistics and supply chain. That move made referrals easier, content more focused, and sales more relevant.
“The evidence was clear: our happiest clients, longest relationships, and best outcomes were in logistics. So why not own that?”
3. How Headway Thinks About Content
Jacob was hired to get content off the founder’s plate. But instead of chasing SEO keywords, he focused on real-world pain points from their dev and design teams.
The result? High-trust content that attracts serious buyers. Not vanity traffic.
“Our videos weren’t short. They were full presentations, sometimes over an hour, with Q&A. And those built a ton of trust.”
4. Referral Programs That Actually Reward People
Headway keeps things casual now but plans to roll out a more formal partner portal for referrals. In the meantime, they send real money—not mugs—to thank people who help close business.
“It’s basically a marketing or sales expense. So yeah, we’re going to thank you properly.”
5. Where Headway is Headed
Headway’s future may include more vertical-specific spinouts like Intermode, a deeper play into training and education, and maybe even a talent pipeline that helps clients hire people trained in their process.
“We’re optimistic, but we’re learning to pace ourselves. First, we’re making sure the current bets are solid before launching new ones.”
Notable Quotes
“If copycatting worked, everyone would be rich.”
“We don’t talk about ourselves enough—that’s the feedback we get. But we care more about community than ROI.”
“We’ve had Fortune 500 clients find us from YouTube after years of watching.”
Learn More / Get Involved
Follow Jacob on LinkedIn → Jacob’s Profile
Explore Headway’s work → headway.io
Interested in collaborating with Headway? → Join the Headway Partner Network
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