Industries We Serve

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 We understand the unique pressures faced by leaders in the Lloyd’s and specialty insurance market: underwriting discipline in volatile conditions, the weight of market cycles, cultural integration post-M&A, and the challenge of attracting and retaining next-generation talent.

What sets our coaching apart is a deep appreciation of complexi

 We understand the unique pressures faced by leaders in the Lloyd’s and specialty insurance market: underwriting discipline in volatile conditions, the weight of market cycles, cultural integration post-M&A, and the challenge of attracting and retaining next-generation talent.

What sets our coaching apart is a deep appreciation of complexity — from regulatory demands to relationship-driven broking and capital market alignment.

Jonathan Gillespie brings 25+ years of board-level experience across high-pressure, regulated industries and global transformation projects. He’s worked with P&L owners, senior brokers, and strategy leads navigating tough calls, legacy systems, and market evolution. He knows what leadership under scrutiny feels like — and how to build confidence, capability, and clarity at pace.

Whether you're refining your portfolio strategy, stepping into ExCo, or aligning your syndicate culture, Hawthorn Hill provides executive coaching that’s commercial, confidential, and built for leaders in high-stakes roles.

  Few industries evolve as quickly — or demand as much adaptability — as media and marketing. The shift from analogue to digital, brand to performance, in-house to outsourced, has reshaped what effective leadership looks like across agencies, platforms, publishers, and client organisations.

Hawthorn Hill was built with this landscape in mi

  Few industries evolve as quickly — or demand as much adaptability — as media and marketing. The shift from analogue to digital, brand to performance, in-house to outsourced, has reshaped what effective leadership looks like across agencies, platforms, publishers, and client organisations.

Hawthorn Hill was built with this landscape in mind. Our team has led large-scale transformation, commercial redesign, and organisational change across global media, technology, and consulting environments. We understand the pressures on CMOs, agency leaders, and client-side executives operating in markets defined by volatility, creativity, and scrutiny.

Our coaching and advisory work helps leaders drive clarity, cohesion, and forward momentum — whether navigating transformation, strengthening team culture, or preparing for a critical next step. The approach blends deep industry experience with world-class professional coaching practice.

This isn’t generic leadership development. It is specialised support for commercial storytellers, growth leaders, and industry change-makers who need pace, precision, and perspective.

 Leadership in invested-capital environments is unforgiving. PE and VC-backed executives must deliver clarity, pace, and returns under pressure — where every decision affects value.

Hawthorn Hill operates in this space. We blend coaching, advisory, and alignment work to strengthen the leaders who drive capital performance. Our experience a

 Leadership in invested-capital environments is unforgiving. PE and VC-backed executives must deliver clarity, pace, and returns under pressure — where every decision affects value.

Hawthorn Hill operates in this space. We blend coaching, advisory, and alignment work to strengthen the leaders who drive capital performance. Our experience across transformation, deal cycles, and regulated markets means we understand both the behavioural demands and the commercial stakes.

We support founders, CEOs, and investment teams with:

• Executive coaching with measurable impact
• Alignment and cohesion for senior teams
• Strategic advisory to sharpen decisions and operating rhythms
• Fractional support to embed clarity and execution discipline

We help leaders cut through noise, act with conviction, and move faster with less friction — delivering the clarity, alignment, and resolution that invested capital demands.