Pentland Brands: Flexible legal expertise for a global lifestyle multi-brand powerhouse

Client Profile: Pentland Brands

Pentland Brands is a UK-based global brand management company that owns and licenses a portfolio of sports, outdoor, and fashion brands including Speedo, Ellesse, Berghaus, Canterbury, and Endura. Founded in 1932 as a shoe manufacturer, the privately held family business has evolved into a major player in the athletic and lifestyle apparel industry.

The Challenge: Fast response to urgent needs

Pentland Brands is one of the world’s leading privately-owned sports, outdoor, and lifestyle companies, home to household names spanning footwear, apparel, and equipment. With a broad commercial portfolio and an in-house legal team under constant pressure, the business needed rapid, high-quality legal support — without the overhead of a traditional law firm.

Pentland required experienced legal cover across two separate engagements within a short timeframe. The first was a data protection specialist for a broad three-month role from early December, working four days a week — covering core DP work alongside e-commerce, IT and technology contracts (SaaS and outsourcing), international distribution and licensing agreements, and competition law. The second was a senior commercial lawyer to step in immediately on a full-time or four-day week basis for three to four months, covering a similarly wide remit, assumed inside IR35.

Both roles required someone who could hit the ground running at pace and integrate seamlessly — not just technically capable, but the right fit for a commercially sophisticated, high-performing environment.

The Obelisk Approach

From the first briefing call, Alastair Kilgour at Pentland felt the difference. Obelisk worked quickly to understand not just the technical requirements but the working culture of the business. Candidates were pre-filtered for professional and cultural fit, and options were turned around promptly — because when the need is urgent, speed and quality must go hand in hand.

The Lawyers

For the data protection and broader commercial role, Obelisk placed a commercially focused solicitor with over fifteen years’ experience across the financial services and technology sectors. With a proven track record of working closely with senior stakeholders to manage risk and secure the best contractual outcomes, she brought significant weight to the engagement — including experience renegotiating a multimillion-pound contract with the BBC, navigating complex EU tender processes, and delivering an £8bn fund outsource project. She had also built a legal function from scratch, giving her the breadth and adaptability a role of this kind demands.

For the second engagement, Obelisk placed a lawyer who had trained at a Magic Circle firm, qualifying into Capital Markets, before moving in-house to a major international securities business. There she led on corporate governance, regulatory implementation, and Board sub-committee support before transitioning into a broad generalist commercial role. Her experience spans reviewing, drafting, and negotiating MSAs, SaaS agreements, licensing agreements, consultancy agreements, and NDAs — precisely the profile Pentland needed.

The Outcome

Obelisk placed lawyers into both roles, delivering a combined 744.75 hours of high-quality legal support across the two engagements. The service was agile, the candidates were strong, and the process was smooth from instruction to invoice.