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: ExCo members · Founders · Senior Leaders · 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: Senior Leadership teams · Founders · VCs & PE Firms · New CxOs
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
Jonathan Gillespie, Co-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.
Sarah Speake, Co-Founder
Sarah draws on three decades of leadership at the intersection of technology, media, and marketing to help senior executives and teams perform with clarity and purpose. A former Global CMO and International Sales Director, she has spent over 20 years on corporate boards and seven as a Non-Executive Director and growth consultant — experience that grounds her coaching in commercial reality and organisational empathy.
Her practice focuses on alignment: between board and brand, ambition and execution, individual intent and collective momentum. Known for her energy, candour, and pragmatic optimism, Sarah helps leaders cut through complexity to act with confidence and impact.
Before joining Hawthorn Hill, she founded Speake Volumes to champion women in leadership and to help organisations embed purposeful growth.
Our Services
Executive Coaching
Organisational Capability & Fractional Leadership
Leadership Team Alignment
Clarity in complexity. Alignment in purpose. Resolution in challenge.
We work 121 with CEOs, founders, and senior executives on the decisions, behaviours, and patterns that determine performance.
We combine behavioural insight with operator-level judgement — helping leaders navigate complexity, sharpen execution, and unblock what’s slow
Clarity in complexity. Alignment in purpose. Resolution in challenge.
We work 121 with CEOs, founders, and senior executives on the decisions, behaviours, and patterns that determine performance.
We combine behavioural insight with operator-level judgement — helping leaders navigate complexity, sharpen execution, and unblock what’s slowing them down.
What we solve for:
- Personal clarity
- Leadership drift
- High-stakes decisions
- Operating rhythm breakdown
- Role transitions
- Founder friction
- Pre-exit pressure.
Leadership Team Alignment
Organisational Capability & Fractional Leadership
Leadership Team Alignment
Clarity in vision. Alignment in execution. Resolution through action.
Most teams struggle not because of strategy, but because of inconsistent expectations, misaligned behaviour, and a lack of a shared operating rhythm.
Using CAR, we reset the clarity of mandate, align behaviour, surface drift, and rebuild the team into a cohesive deci
Clarity in vision. Alignment in execution. Resolution through action.
Most teams struggle not because of strategy, but because of inconsistent expectations, misaligned behaviour, and a lack of a shared operating rhythm.
Using CAR, we reset the clarity of mandate, align behaviour, surface drift, and rebuild the team into a cohesive decision-making unit.
What we solve for:
- Cohesion & alignment workshops
- Senior Leadership Team coaching (SLT/ELT)
- Behavioural Assessment
- Drift & behavioural telemetry (Drift Tracker™, CAR Diagnostic, Decision Rights Matrix™)
- Conflict repair and mediation within teams
Outcomes: fewer circular discussions, higher trust, cleaner decisions, and a team that moves in-step, not in fragments.
Organisational Capability & Fractional Leadership
Organisational Capability & Fractional Leadership
Organisational Capability & Fractional Leadership
When the system needs more clarity, alignment, and execution discipline.
For organisations facing scale, transition, or instability, CAR provides the structure to rebuild the human operating system — and our fractional operators provide the hands and judgement to run it.
What we solve for:
Fractional Leadership
(CMO, CSO, CPO, CoS, CTO)
Embed
When the system needs more clarity, alignment, and execution discipline.
For organisations facing scale, transition, or instability, CAR provides the structure to rebuild the human operating system — and our fractional operators provide the hands and judgement to run it.
What we solve for:
Fractional Leadership
(CMO, CSO, CPO, CoS, CTO)
Embedded operators aligned to CAR who stabilise momentum, create operating rhythm, and drive execution.
Applying CAR to values, behaviours, leadership signals, communication, and decision cadence.
Diagnostics & Telemetry at Scale
- CAR Diagnostic™
- Drift Tracker™
- Leadership & culture mapping
- Decision Rights Matrix™
Outcomes: a clearer organisation, a predictable rhythm, cultural coherence, and leadership behaviours that enable — not impede — growth.
Hawthorn Hill Proprietary Tools
Leadership Clarity Engine™
60-Day Runway™ for New Senior Hires
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™
60-Day Runway™ for New Senior Hires
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.
60-Day Runway™ for New Senior Hires
60-Day Runway™ for New Senior Hires
60-Day Runway™ for New Senior Hires
For: Newly Appointed Executives, Senior Hires, and Leaders Transitioning into High-Impact Roles
One-line Summary:
A structured, data-informed transition accelerator giving new leaders clarity, confidence, and early momentum in their first 60 days.
Expected Outcome:
Rapid role assimilation, sharper mandate clarity, stronger early decision-making, and measurable leadership traction — supported by CAR diagnostics and optional organisational telemetry.
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 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 min
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.
Deployed Capital
Specialty Insurance
Deployed Capital
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
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.
Some Of Our Great Clients
