Executive Coaching
Strategic Advisory
Mediation

Executive Coaching
Strategic Advisory
Mediation
Clarity in complexity. Growth with purpose. Resolution in challenge.
Leadership today demands more than technical skill—it calls for self-awareness, emotional agility, and strategic clarity. Even the most experienced leaders can feel uncertain in fast-changing environments.
At Hawthorn Hill, we combine 30 years of senior leadership with ac
Clarity in complexity. Growth with purpose. Resolution in challenge.
Leadership today demands more than technical skill—it calls for self-awareness, emotional agility, and strategic clarity. Even the most experienced leaders can feel uncertain in fast-changing environments.
At Hawthorn Hill, we combine 30 years of senior leadership with accredited executive coaching to help leaders unlock breakthrough performance—for themselves and their organisations.
Our approach empowers you to:
Led by Jonathan Gillespie, a qualified Meyler Campbell coach and EMCC member, our coaching is grounded in deep commercial insight and real-world experience.
Clarity in vision. Growth with precision. Resolution through action.
Hawthorn Hill helps founders turn ambition into execution—advising on strategy, culture, and leadership to build businesses that thrive in uncertainty.
We bring blue-chip experience as CEO, COO, CMO, and CRO to support early-stage leaders in navigating complexity and acce
Clarity in vision. Growth with precision. Resolution through action.
Hawthorn Hill helps founders turn ambition into execution—advising on strategy, culture, and leadership to build businesses that thrive in uncertainty.
We bring blue-chip experience as CEO, COO, CMO, and CRO to support early-stage leaders in navigating complexity and accelerating growth.
Our advisory model blends hands-on strategy with targeted coaching to help you:
With Hawthorn Hill, you gain a trusted partner—not just to plan, but to lead through change and deliver measurable results.
[Explore Strategic Support]
Clarity in conflict. Growth through dialogue. Resolution that lasts.
Disputes drain time, trust, and productivity. At Hawthorn Hill, we help individuals and organisations move forward—quickly, constructively, and with dignity.
Our mediation services are tailored to leadership, workplace, and commercial contexts, offering:
Clarity in conflict. Growth through dialogue. Resolution that lasts.
Disputes drain time, trust, and productivity. At Hawthorn Hill, we help individuals and organisations move forward—quickly, constructively, and with dignity.
Our mediation services are tailored to leadership, workplace, and commercial contexts, offering:
Whether navigating internal tensions or high-stakes negotiations, we bring empathy, rigour, and results.
LSM-accredited mediator. CMC standards. Commercially grounded.
[Learn About Mediation]
At Hawthorn Hill, we empower leaders to make sense of complexity, unlock sustainable growth, and resolve conflict with courage and clarity. Our work spans three interconnected domains — executive coaching, strategic advisory, and mediation — all anchored in a belief that clarity drives action, growth requires intention, and resolution unlocks momentum.
Executive Coaching for Self-Aware Leadership
Clarity unlocks pace, influence, and better decisions. We help leaders see themselves clearly — and lead with purpose.
Tools: Modular Programme · Clarity Diagnostic™ · HH Coaching Model™
Clients: Founders · Senior Leaders · C-Suite Talent · Change Agents
Coaching & Advisory for Scalable Leadership
Scaling well requires more than momentum — it demands clarity, discipline, and trusted partners. We support founders, operators, and investors driving high-growth environments.
Tools: Modular Programme · Growth Sprint™ · Strategic Advisory for Founders & Funds
Clients: Startups · Founders · VCs & PE Firms · New CxOs · High-Growth Team
Coaching, Advisory & Mediation for High-Stakes Challenges
When tension rises or trust falters, resolution is key. We bring clarity, neutrality, and pace to stuck situations.
Tools:
Resolution Sprint™ · Leadership Mediation · CGR Framework
Clients:
Boards · Founder Teams · Executive Partnerships · Legal & HR Leaders
Jonathan Gillespie is a seasoned Executive Coach, Business Strategist and accredited Mediator who empowers senior leaders to thrive amid complexity and disruption.
With over 30 years of global experience across technology, insurance, media and consulting, Jonathan has led digital transformations, commercial turnarounds, and high-impact growth initiatives across sectors undergoing profound change.
For: Venture Capital & Growth Equity Portfolios
One-line Summary: A governance-ready clarity system for founders — aligning leadership, decision-making, and investor confidence.
Expected Outcome: Increased founder resilience, sharper governance, and measurable alignment across leadership, investors, and strategic direction — benchmarked for LP and partner reporting.
For: Professional Services and Transformation Consultancies
One-line Summary: A hybrid coaching-mediation system designed to de-risk leadership performance in high-stakes, high-conflict environments.
Expected Outcome: Faster resolution of executive tensions, smoother transitions during crisis or transformation, and improved leadership continuity without costly litigation or attrition.
For: PE-backed Executives, First-Time CEOs, and Functional Leaders Moving to the Board
One-line Summary: A structured, metric-led sprint preparing leaders for board-level responsibility, scrutiny, and influence.
Expected Outcome: Clear articulation of board value-add, elevated strategic maturity, and investor trust — underpinned by a proprietary benchmarking and coaching framework.
At Hawthorn Hill, 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 apprec
At Hawthorn Hill, 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 change as fast — or demand as much resilience — as media and marketing. The shift from analogue to digital, brand to performance, in-house to outsourced, has reshaped what leadership looks like in agencies, platforms, publishers, and client organisations.
Jonathan Gillespie has lived that change — launching YouTube’s monetis
Few industries change as fast — or demand as much resilience — as media and marketing. The shift from analogue to digital, brand to performance, in-house to outsourced, has reshaped what leadership looks like in agencies, platforms, publishers, and client organisations.
Jonathan Gillespie has lived that change — launching YouTube’s monetisation model across Europe, leading M&A strategy at Guardian Media Group, and running global marketing and media transformation initiatives for Google, Omnicom, and Cognizant.
At Hawthorn Hill, our coaching helps CMOs, agency leaders, and client-side innovators lead with clarity in uncertain markets. Whether you’re driving a transformation, rethinking team culture, or preparing for your next leadership move, our coaching blends lived industry experience with world-class practice (Meyler Campbell trained, EMCC aligned).
This isn’t generic leadership development. It’s tailored coaching for commercial storytellers, growth leaders, and industry change-makers.
Leadership in financial services has never been more demanding. Today’s executives face macroeconomic instability, digital disruption, regulatory change, and increasing expectations from boards, regulators, and clients alike.
Hawthorn Hill delivers coaching tailored for this environment — where decisions carry risk, perception shapes outc
Leadership in financial services has never been more demanding. Today’s executives face macroeconomic instability, digital disruption, regulatory change, and increasing expectations from boards, regulators, and clients alike.
Hawthorn Hill delivers coaching tailored for this environment — where decisions carry risk, perception shapes outcomes, and clarity is currency.
Jonathan Gillespie brings experience in enterprise-scale transformation, stakeholder engagement across regulated markets, and leadership of global consulting teams. He’s advised and coached senior leaders managing portfolios worth hundreds of millions — with the discretion, precision, and insight that financial executives require.
Whether you’re in asset management, retail banking, fintech, or professional services, Hawthorn Hill’s coaching combines strategic acuity with leadership depth. We help you see around corners, lead through ambiguity, and accelerate your own development with rigour and trust.
You are individual and special.
Let's recognise that and meet in person
Langton Road, Speldhurst, Tunbridge Wells, TN3 0NR, United Kingdom
Hawthorn Hill