How Headway Marketing Went from “Glorified Freelancer” to $30K + MRR
"Productive." — That’s how Tanner Hobin, CEO of Headway Marketing, describes his experience inside Nigel’s Agency Mentoring program.
The Client
Name: Tanner Hobin
‍Agency: Headway Marketing
‍Location: St. Louis, Missouri
‍Niche: Full-service digital marketing & web development
‍Team Size at Start: 1 (plus one underused contractor)
‍Mentorship Period: Aug 2024 – Nov 2024
‍MRR Growth: $18K → $30K+ in 4 months
‍One Word to Describe the Experience: Productive
Watch full interview with Tanner Hobin in the video below.
Before Mentorship: An Agency in Name, a Freelancer in Practice
When Tanner left a 9-year career at Nestlé and launched Headway Marketing, he took with him two decades of corporate and agency-side experience. But what he stepped into didn’t quite feel like an agency yet.
"Looking back at that time… I don’t really think I was running an agency. It was kind of a glorified freelance operation." - Tanner Hobin
With a single client bringing in $18K/month (split across 3 projects), he was fully focused on delivery. No pipeline. No inbound or outbound. No project management tool. No clear systems. And worst of all, no capacity to delegate.

His operations tech stack? Non-existent.

His team? A lone contractor, mostly underutilized.

His calendar? Full of firefighting and fulfillment.
"I feared bringing more people into the chaos. Because I didn’t have anything to onboard them with." - Tanner Hobin
Tanner knew the agency had potential - but also that it wouldn’t scale unless something changed.
Tanner knew the agency had potential - but also that it wouldn’t scale unless something changed.
The Mentorship: Building a Foundation for Growth
How Tanner Found Nigel (And Why He Reached Out)
Tanner had followed Nigel on LinkedIn for months. But the moment of action came after seeing a post with an ICP Grid. It clicked.
“He posted an ICP grid. I said, ‘If there’s still a spot open in the mentorship program, I’d love to learn more.’” - Tanner Hobin
At that point, he wasn’t looking for fluff. He wanted structure. Not just in tactics, but across the entire agency - positioning, systems, partnerships, operations, and mindset.

What Tanner found inside Agency Mentoring was exactly that: structure and community.
Operational Foundations
Tanner started implementing - fast.
✅ Asana for task and project management

✅ Loom for async feedback, training, and SOP creation

✅ HubSpot CRM restructured to capture inbound leads

✅ Google Workspace finally organized and standardized

✅ Team-wide tools: Grammarly + ChatGPT Teams
“If I hadn’t joined, it would’ve taken me 18–24 months to get where I am now. This shrank the learning cycle.”
Positioning & Value Proposition
Tanner’s agency wasn’t niche - and that was by design. But the messaging didn’t resonate… yet.
“I was hell-bent on building a full-service agency. But I didn’t know how to explain it.”
Nigel and the team helped Tanner find language that cut through:
“I tell prospects: I’m your fractional marketing department. I know your list of to-do’s is growing - I’ll take it off your plate.”
That shift made closing deals easier and onboarding smoother.
Strategic Partnerships
Partnerships weren’t even on Tanner’s radar before the program. But through connections in the cohort and from Nigel himself, they became a pillar of his growth. Notably:
“You guys helped me connect with people I’d never have met. That alone was worth the investment.”
Mindset Reset: From Paralyzed to Proactive
Tanner referenced a quote that haunted him before he joined:
“How did you go bankrupt? Gradually, then suddenly.” - Ernest Hemingway
It reflected his fear - of losing a client, of losing momentum, of not being enough. But the mentorship helped him rewrite that quote:
“Now I think of it in reverse. My scale-up was slow at first… then all of a sudden.” - Tanner Hobin
He stopped fearing loss. He embraced leadership. And he started building a company he was proud of.
“I used to be paralyzed by the thought of losing a client. Now I kind of want to lose one - just to prove we can take it.” - Tanner Hobin
After Mentorship: Headway Hits Its Stride
Today:
“Now I wake up and see Asana tasks marked complete. I’ve never felt more confident in where we’re going.”
Why It Worked: Shrinking the Learning Curve
The real ROI wasn’t just revenue. It was acceleration.
“Most people don’t realize - it’s not about the money. It’s about shrinking the time to failure, so you can scale faster.”
Tanner leveraged:
“I don’t know how Nigel finds such great people, but he does. I still talk to people from the cohort regularly.”
Final Reflections: If He Could Talk to Past Tanner
If he could speak to the Tanner from before the mentorship, he’d show him Rory McIlroy’s emotional final putt at the Masters:
“That’s your moment. This is the group that’s going to get you there. Just trust the system.”
Would Tanner do it again?
“No question. 3x ROI in 4 months. But more importantly - the clarity and control? That’s priceless.”
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