About Us

Oliver Sweeney (www.oliversweeney.com) has been making shoes (and later clothing) for over 30 years. We’ve built a reputation for craftsmanship, design flair, and a slightly mischievous sense of British style. Today, around 80% of our sales are direct-to-consumer through our website retail, with the rest through carefully chosen wholesale partners. 30 % of our revenue now comes from clothing as we move to become a lifestyle fashion brand rather than simply a shoe business.

We’re at an exciting point. Our long-serving CEO – better known as Cobbler-in-Chief, Tim Cooper – is preparing to hang up his boots. We’re now looking for someone to step in as Managing Director. You’ll work closely with Tim through a handover, before taking the reins and leading Oliver Sweeney into its next chapter.

The Role

We’re a small, well-run business, with enormous potential and we are looking for an outstanding individual who can take us to the next level of growth, through setting a clear strategic and get stuck into the detail for its delivery.

You’ll be steering a profitable brand, but also helping us unlock the next wave of growth across D2C, e-commerce, and wholesale. You’ll need to love the numbers as much as the design, and be just as comfortable talking P&L with our shareholders as you are talking product with our designers.

What You’ll Be Doing

• Lead the way: Work with the Board and Chair to shape our future and inspire the team to follow in its delivery.
• Build the brand: Grow and protect what makes Oliver Sweeney distinctive while pushing our ranges forward. You’ll be hands-on with product development and range planning – from concept through to delivery – ensuring collections are commercially balanced and creatively distinctive. We are looking for someone with vision and design flair who can help us evolve our range into a truly compelling offering which is delivered in a consistent and creative way across all consumer touchpoints.
• Product sourcing & suppliers: Manage sourcing and supplier relationships to maintain quality, reliability, and margin. Work with factories and partners to ensure the right balance of craftsmanship, cost efficiency, and timely delivery. Keep a close eye on supplier performance and negotiate effectively.
• Drive growth: Continue to develop our D2C offering – from digital marketing and customer acquisition to retention and lifetime value. Make sure the online journey (site experience, fulfilment, service) is best-in-class and commercially effective. Develop new strategies which will build scale for the business.
• Wholesale Management - Strengthen our wholesale offering by building effective relationships that deliver profitable returns and are sustainable.
• Finance & numbers: Own the P&L, manage budgets, and set clear KPIs. Stay across cash flow, stock turns, and margin analysis, ensuring the business remains profitable and agile. Spot risks and opportunities early, and make confident, numbers-backed decisions. Oversee the monthly board reporting and measurement of performance against agreed dashboard of metrics
• Build culture: We’re big on energy, enthusiasm, and collaboration – so you’ll need to foster that and lead by example. With a team of just 17, you’ll be close to the action – whether that’s signing off a marketing campaign, checking sourcing efficiencies, reviewing the week’s digital performance, or sitting down with design to shape the next range. We are a very happy business to work in, and we intend to stay that way!
• Plan the handover: Work alongside Tim Cooper to develop an effective and measurable handover plan. (We are assuming this is a three month period.)

What We’re Looking For

• 10+ years’ experience in ideally fashion, footwear or apparel.
• Strong understanding of product design, range planning, and sourcing, with experience managing supplier relationships.
• Track record in e-commerce growth (digital marketing, site optimisation, customer journey) and wholesale development.
• Commercially sharp – confident with financials, P&L, cash flow, and KPIs.
• Strategic thinker who’s also happy to roll up sleeves in a small business environment.
• A natural leader who’s energetic, collaborative, and good fun to work with.

The Opportunity

• A profitable, design-led British brand to lead and grow.
• A clear succession plan, with mentoring from our outgoing Cobbler-in-Chief.
• The chance to make a real impact – we’re small enough that your ideas will shape the future.
• A competitive package with performance incentives.
• A team that’s passionate, collaborative, and genuinely enjoys what they do.