More than Coaching. An Operating System for Sustainable leadership
Our Services
Executive Coaching
Strategic Advisory for Founders & SMEs
Strategic Advisory for Founders & SMEs
Clarity in complexity. Alignment in purpose. Resolution in challenge.
We help leaders cut through uncertainty with accredited, real-world coaching grounded in boardroom experience.
You gain:
- Sharper decisions under pressure
- Alignment of purpose and goals
- Confidence through complexity
- Resilient, high-performing teams
[Book a Discovery Call]
Strategic Advisory for Founders & SMEs
Strategic Advisory for Founders & SMEs
Strategic Advisory for Founders & SMEs
Clarity in vision. Alignment in execution. Resolution through action.
We turn ambition into execution — blending strategy, culture, and leadership coaching.
You gain:
- Clear, confident growth plans
- Smarter decisions under strain
- Scalable, aligned cultures
- Fewer blind spots blocking growth
[Explore Strategic Support]
Mediation
Strategic Advisory for Founders & SMEs
Mediation
Clarity in conflict. Alignment through dialogue. Resolution that lasts.
We help leaders and teams resolve disputes quickly, constructively, and with dignity.
You gain:
- A neutral, confidential space
- Outcomes that restore focus
- An expert mediator with leadership experience
[Learn About Mediation]
About Hawthorn Hill
CLARITY. ALIGNMENT. RESOLUTION
At Hawthorn Hill, Clarity · Alignment · Resolution are not services — they are our operating model.
We help leaders cut through complexity, align purpose with strategy, and resolve the conflicts that stall progress.
Through coaching, advisory, and mediation, we equip leaders to act with confidence, sustain growth, and move forward with momentum.
CLARITY
Executive Coaching for Self-Aware Leadership
Clarity unlocks pace, influence, and better decisions. We help leaders see themselves clearly — and lead with intent.
- Cut through noise to spot what really matters
- Stay true to your values when pressure tests them
- Handle uncertainty without losing direction
- Make decisions faster — and stand by them
Tools: Leadership Clarity Engine™ · CAR Telemetry™
FOR: Founders · Senior Leaders · C-Suite Talent · Change Agents
ALIGNMENT
Strategic Advisory for Growth & Scale
Scaling isn’t just about speed — it’s about staying aligned. We keep leaders, teams, and investors moving in the same direction.
- Match leadership capacity to the demands of growth
- Keep decisions quick without breaking cohesion
- Pull strategy and people into the same direction
- Protect alignment as complexity builds
Tools: Boardroom Sprint™ · CAR Telemetry™
FOR: Startups · Founders · VCs & PE Firms · New CxOs · High-Growth Teams
RESOLUTION
Coaching & Mediation for High-Stakes Challenges
When tension rises or trust falters, resolution restores focus, pace, and momentum.
- Unlock stalled relationships before they calcify
- Tackle tough conversations without avoidance
- Defuse founder or board rifts before they derail value
- Make high-stakes calls with confidence under pressure
Tools: Resolution-Led Leadership™ · CAR Telemetry™
FOR: Boards · Founder Teams · Executive Partnerships · Legal & HR Leaders
About the Founder
Jonathan is a distinguished executive coach, trained by Meyler Campbell (Europe’s premier coaching programme, where he graduated with distinction), and a roster coach for Balderton Capital, supporting founders and leaders across one of Europe’s leading venture capital portfolios.
He brings more than 25 years of senior leadership experience across media, technology, consulting, and founder-led businesses. His career has spanned board roles, global transformations, and start-up ventures, giving him a depth of perspective on the pressures leaders face in high-growth, high-stakes environments.
At Hawthorn Hill, Jonathan has developed the CAR framework — Clarity, Alignment, Resolution — which underpins his Coaching+ approach. He combines deep 1:1 coaching with data tools to make leadership alignment visible and actionable, helping leaders avoid drift and sustain performance.
Hawthorn Hill Proprietary Tools
Leadership Clarity Engine™
Leadership Clarity Engine™
Leadership Clarity Engine™
For: Venture Capital & Growth Equity Portfolios
One-line Summary: A governance-ready clarity system for leaders — aligning leadership, decision-making, and investor confidence.
Expected Outcome: Increased resilience, sharper governance, and measurable alignment across leadership, investors, and strategic direction — benchmarked for LP and partner reporting.
Resolution-Led Leadership™
Leadership Clarity Engine™
Leadership Clarity Engine™
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.
Board Readiness Sprint™
Leadership Clarity Engine™
Board Readiness Sprint™
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.
Industries We Serve
Specialty Insurance
Specialty Insurance
Specialty Insurance
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.
Marketing Services
Specialty Insurance
Specialty Insurance
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.
Finance
Specialty Insurance
Finance
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.
We bring experience in enterprise-scale transformation, stakeholder engagement across regulated markets, and leadership of global consulting teams. We’ve 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.