How a Dev Agency Built Demand Through Community & Deep Content
Headway’s “Be Helpful” Growth Engine: Content, Community, and a Smart Industry Spin-Off (Intermode)
Behind the Agency Podcast with Jacob Miller, Marketing & Brand Manager at Headway
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Prefer the highlights? Key takeaways and summary below.
TL;DR – Key Takeaways
Headway started as 4 freelancers who were tired of how most companies “do design + dev,” so they built a better process and banded together.
Their “growth channel” wasn’t a channel. They built community (Digital Fertilizer → Startup Wisconsin) because they wanted it to exist—not to farm leads.
They tried the usual positioning moves (B2B SaaS, Series A+, “we do UX audits only,” etc.) and found the hard truth: copy/paste positioning doesn’t copy/paste results.
Headway eventually embraced being a strong-process generalist, but created a focused spin-off (Intermode) to win with industry clarity.
Intermode picked logistics/supply chain because ~30–35% of Headway’s past work was already there—and it included their biggest + happiest clients.
Content that wins = real problems from real projects, not “what keywords should we target?” They turned team experience into articles, videos, templates, and downloads.
Long, high-depth YouTube content worked (40–90 min presentations + Q&A). They had Fortune 500 folks watch for years before finally reaching out.
Referrals work better when you make it easy to “place you.” “Logistics software team” is an instant mental hook; “dev agency” is a fog.
Their referral program is paid (percentage of contract for a limited term). They see it as “marketing cost, but more fair.”
Meet the Guest
Jacob Miller is the Marketing and Brand Manager at Headway, a dev agency that helps teams design and build software with a strong, repeatable process. Jacob came in with a background in video production, photography, audio, and writing, and helped Headway build a content engine that now drives significant inbound traffic and long-cycle trust.
Headway also launched a focused subsidiary, Intermode, aimed at logistics and supply chain companies that need better software outcomes.
(Before Headway, Jacob’s background was hands-on media + writing, which shaped how Headway’s content became “teach-first,” not “sell-first.”)
Episode Summary
1. From freelancers to agency (and why Headway exists)
Headway started in 2015 with four partners who were originally working as contractors/freelancers. They kept getting pulled onto the same projects and got fed up with how messy and ineffective the usual design/dev process was—so they built their own approach and turned it into a company.
Jacob joined in 2017 and has been there nearly 8 years (with Headway approaching its 10-year anniversary).
2. The main tension: agencies want “a niche” but reality is messy
They went through the same identity struggle most agencies do: “We should niche down,” “We should productize a service,” “We should target Series A+,” etc.
But Jacob’s take was refreshingly honest: trying what worked for someone else doesn’t mean it’ll work for you.
“Just because someone else does it and we try it doesn’t mean it’ll work for us… if copycatting worked, everybody would be rich.”
3. Their unique way of solving it: be a generalist with a serious process
Headway landed on something a lot of agencies are scared to admit out loud:
They’re okay being a generalist because their process is the product.
The catch: it’s hard to communicate that clearly in marketing. “We can help anyone if they’ll follow our process” doesn’t always “click” fast.
4. The big move: spin off an industry-focused brand (Intermode)
Instead of forcing Headway to be narrowly positioned, they created Intermode as a separate industry brand focused on logistics and supply chain.
Why that industry?
30–35% of Headway’s past work was already in that space
It included their biggest projects
The clients were their happiest and actually followed the process
They did industry interviews to confirm the need and buying behavior
The result: sales conversations got easier because people could finally place them.
5. The simple positioning lesson most people miss
This part hit hard:
When you say: “Do you know anyone who needs dev/design?” people blank.
When you say: “Do you know anyone in logistics/supply chain building software?” people suddenly think of 3 names.
It’s the “Cheesecake Factory menu” problem. Too many options = no decision.
6. Content philosophy: stop chasing keywords first
Jacob didn’t start with SEO tools asking, “What do we rank for?”
He started with: What problems are we solving on real client work?
Then they made content from that:
deep videos (presentations + Q&A)
articles
templates and downloads (UX audit templates, design system assets, etc.)
Afterwards, he’d apply SEO best practices without ruining the usefulness.
Over time, it stacked into a real inbound engine:
500+ pages
100k+ website visitors (driven by the content library)
7. YouTube: the “wrong audience” myth (and why it’s outdated)
Jacob gave a great counter to the common agency belief:
“Our buyers aren’t on YouTube / TikTok.”
Reality: people watch YouTube on their TVs now. Decision-makers learn there too.
They had Fortune 500 people watching their content for 2–3 years before submitting a form.
That’s not a “lead gen hack.” That’s compounding trust.
8. Referral program: casual today, formal tomorrow
They currently run a casual referral partner setup:
They offer a percentage of the contract
There are term limits
They want to build a dashboard where partners can submit + track referrals
They see it as a fair trade:
“If a referral becomes a $100k contract, a mug is insulting. Pay people.”
Also: they’re careful about not treating it like cold outbound.
If you don’t have a real relationship, leading with “here’s my referral commission” feels gross.
9. Where Headway is headed (BHAGs + reality checks)
Jacob described Headway’s “big circles” vision:
Education (courses, possibly more later)
Talent (training strategic designers/devs; potentially placing talent with clients)
Community / philanthropy (Startup Wisconsin)
Key maturity move: they’re getting more sober about capacity.
Lots of ideas ≠ ability to execute them all at once.
Notable Quotes
“If copycatting worked, everybody would be rich.”
“We genuinely care about building a community… it’s not about ROI and leads.”
“YouTube works for you if you’re putting out stuff that’s actually valuable.”
“The more specific we get, the better.”
Learn More / Get in Touch
Headway: headway.io
Headway Partner Network: headway.io/partner-network
Linkedin: Jacob Miller
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