Hi, I'm Jack Willoughby

I build brand and marketing systems that create, capture, and cultivate market interest.

Nearly a decade building brand and marketing systems across workwear, streetwear, fitness, and ecommerce. Currently Head of Brand & Marketing @ Xpert Workwear, running full-ecosystem strategy across B2B, wholesale, and DTC. I’m also peer-vetted into MarketerHire’s top 1% network as an advisory CMO and brand strategist. MSc Marketing | MCIM.

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Xpert Workwear
Growing an agri-workwear brand

Cottonmount Trading
Transforming a legacy wholesaler

OutsideIn
Scaling a DTC streetwear brand

PulseFit
Building iconic fitness brands

Overflow Archive
Ventures, Projects & More

Motivation is short term. Perception is more durable. Change how someone sees something and you change how they understand it, talk about it, act on it and choose it. That is the work I have built my career around.

How I Think

The penny dropped for me early in my career while I was selling gym memberships. I quickly realised that people rarely just buy a membership, an offer, or a discount. They buy the shift it represents, whether that is confidence, progress, identity, status, belonging, or relief from a problem they have carried for too long. They are buying a version of themselves they wanted to become.

Once I saw that human truth, I started seeing the exact same pattern everywhere regardless of industry. It’s why I treat brand and marketing as a single demand function designed to create, capture, and cultivate that exact market interest.

What I've Built

That thread has shaped most of my work, from building brands and sharpening positioning to creating growth systems, improving customer journeys, and making marketing more useful inside a business.

Since then, I’ve built and scaled brands across workwear, streetwear, fitness, and ecommerce. I’ve worked as a founder, consultant and in-house marketing leader, building brand strategy, channel infrastructure, campaigns, teams and operating rhythms behind commercial growth.

Most recently, that looks like the 50-year-old wholesaler I’ve taken through a complete rebrand and turned into a brand people choose. Own-brand revenue moved from under 40% to over 90%, the digital estate I built from zero now runs as a multi-million-pound operation across D2C, Amazon and B2B, and the brand sits in 900+ stores across the UK and Ireland, with campaign creative featured on Ads of the World. Before that, I scaled a purpose-driven streetwear start-up 4x in two years.

Away from work, I’m a proud dad and I write about brand, perception and the reality of building something that matters. I care about the standard of the work, but also about making marketing useful, commercially relevant and honest

Snapshot

Xpert Workwear // Head of Brand & Marketing // Since 2021

Cottonmount Trading // Head of Brands & Marketing // Since 2021

Advisory CMO & Brand Specialist // MarketerHire Elite Network // Since 2021

PulseFit // Founder // Since 2019

OutsideIn // Marketing // 2019-2021

Early Career // Digital Marketing // Sales // Consulting // 2017-2019

Qualifications: MSc Marketing · MCIM · BSc (Hons) Sports & Exercise

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"Worked with Jack across a couple of bigger branding projects now for a high end clothing manufacturer. Jack has an easy going manner but shows a thorough approach to the projects we’ve collaborated on. Deliverables were what we’d anticipated and that strikes me as a result."

Alasdair McBroom

Wolfhound

"Working with Jack has been an absolute pleasure. His exceptional management skills made the entire collaboration seamless and efficient. Right from the start, he set clear expectations and provided all the necessary resources for me to complete the project easily and efficiently. I highly recommend Jack as an excellent digital marketing professional for any project."

Kris Byers

Horrible Brands

"Jack has been a real asset to the business.

As Head of Brand & Marketing, he translates brand vision into clear, effective campaigns, combining creativity with structure. He understands the customer, supports the sales team with practical materials, and aligns marketing with real commercial goals.

Any business would be fortunate to have him."

Ross Wilson

Xpert Workwear

“I can confidently say that Jack is an exceptional manager for freelancers. His effective communication, organisational prowess, and inclusive leadership style have made my experience working with him truly enjoyable. I highly recommend Jack as a marketing manager for any freelancers or team members seeking a supportive and well-organised leader.”

Dave Disbury

Disbury Creative

Latest Thinking

Brand & Marketing, written honestly.
From inside the job.