EXECUTIVE COACH

Strengthening leadership in moments that matter most.

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“PRESSURE DOESN'T CREATE GREAT LEADERS, IT REVEALS WHETHER THEY ARE ALIGNED ENOUGH TO LEAD " - Simon

How simon helps you lead...

At pivotal moments, when pressure mounts and the path forward isn't clear, Simon works alongside CEOs and senior leaders as a trusted coach and confidant, offering the grounded, discreet counsel that restores alignment and helps leaders lead with clarity under sustained pressure.
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This is not conventional coaching. It is a deeply personal partnership for leaders who understand that their inner life and outer leadership are inseparable, creating rare space for honest reflection, so leaders can confront what isn't working and reconnect with the conviction that got them here.
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The result is leadership that moves from force to alignment, being grounded, resilient, and guided by values. For those he works with, it becomes one of the most consequential investments they make, not just in their performance, but in who they are becoming.
Partner with Simon
Trusted by Executives

“Simon has been an invaluable resource in my personal and professional journey towards living my most authentic life.”

Mauricio Serna
SVP Global Head of ESG, Starwood Capital Group

“Simon has been an amazing thought partner… I always leave with another way to think about and activate our work.”

Amy Smith
Chief Brand Officer, TOMS

“Simon is my friend, trusted confidant, and advisory resource… I’m grateful for our partnership.”

Drake Sadler
Co-Founder & Chairman, Traditional Medicinals

“A rare thought leader… humble, brilliant, fun, and committed.”

Letitia Webster
Chief Sustainability Officer, Goldman Sachs Merchant Bank

“Simon is one of the best-in-class humans I know… My highest recommendation.”

Christopher Gavigan
Co-Founder, The Honest Company

Leadership sessions

Simon works with executive and senior teams at moments when clarity, alignment, and judgment matter most, helping leadership groups navigate complexity, cultural change, and the accelerating influence of AI by creating the conditions for honest conversation and decisive direction.
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This is not facilitation as process management. It is focused, high-trust leadership work for teams willing to pause and think together at a higher level, surfacing what is misaligned, clarifying what truly matters, and reconnecting collective intent with operational reality.
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Through immersive sessions and executive forums, Simon helps teams strengthen judgment, rebuild trust, and align around a shared sense of direction, bridging who they are as leaders with how they operate as an organization, and enabling growth that is durable and fit for an AI-shaped future.
Book Simon for your Leaders
A Lasting Impact


“Your session has seen the biggest reach and engagement from all our CA XChange events so far. Definitely triggered people to rethink our campaigns.”

Pedro Monteiro
Global Leadership Development Academy, Heineken

“Simon led an incredibly engaging and insightful workshop for our non-profit mental health partners on crafting a powerful message. The session was interactive, supportive, and full of takeaways.”

Judith Martinez
Director of Social Impact & Inclusion, Rare Beauty & Rare Impact Fund

“Simon led a tailored workshop for our member companies on aligning corporate purpose with the UN SDGs. We were all so impressed by his depth of expertise, attentiveness, and abundant warmth and humor.”

Ilze Melngailis
Senior Director, Business Council for the UN (BCUN)

“From an exclusive conversation with the Executive Leadership Team to a company-wide video presentation to department-specific gatherings, Simon tailored his key messages to deliver the most impact. His time with us was a milestone for us.”

Aaron Sherinian
Senior VP, Global Reach, Deseret Management Corporation

“Simon really delivered. He was able to craft a message for our C-Suite members that resonated, delivered valuable content, and real thought leadership. Leaving the audience with key principles, take away content, and a focus on the future challenges of the sector. Working in the hybrid world of physical and virtual, Simon’s session was exemplary.”

Samantha Blake
Director, Industry Affairs, Australian Food and Grocery Council


"Simon became a trusted advisor and counselor as we navigated through a number of phases, each helping us prepare for the organization's ability to articulate our why more broadly. His passion and expertise, coupled with his experience and organizational savviness, provided us with the ability to reinforce, communicate, and align our organization around a powerful purpose that is as true to our roots as it is to our future.”

Jill Novelo
SVP & Chief of Staff, VSP Vision


“I can't express how thrilled we are about your work with our leadership team. The buzz is still going.”

Jeannie T Bailey
Community Relations, Toyota

What to expect from a session

Strategic Coherence |
Aligning Purpose, Performance, and Sustained Growth
Simon helps senior teams identify where purpose, strategy, and decision-making have drifted out of alignment and guides them back to coherence, so that clearer priorities and sharper judgment drive both performance and credibility over the long term.

‍Virtual or In-person, 3 hours
Value Creation |
Making Sustainability Drive Business Results:
Simon helps senior teams reframe sustainability as a strategic lever for growth and differentiation, moving beyond compliance to identify where it's under-leveraged and how to translate it into a competitive advantage that holds up under scrutiny.

‍Virtual or In-person, 3 hours
Human Advantage |
Building Culture When Machines Share the Work
Simon helps leadership teams identify what must remain distinctly human as AI reshapes work, designing culture so that judgment, trust, and accountability are strengthened rather than eroded by intelligent systems.

‍Virtual or In-person, 3 hours
Leading AI |
Integrating Human Agency and Intelligent Systems
Simon guides senior teams through the strategic, cultural, and ethical implications of AI — helping leaders define where human judgment and accountability must remain so that AI adoption strengthens rather than undermines trust and long-term enterprise value.

‍Virtual or In-person, 3 hours
Brand Narrative |
Turning Strategy into Stories That Drive Growth
Simon helps leadership teams translate strategy into a clear, compelling narrative that aligns stakeholders, sharpens market positioning, and drives consistent storytelling across every touchpoint so that the brand earns attention, trust, and preference over time.

‍Virtual or In-person, 3 hours
Enquiries

For event bookings, keynote requests, or media opportunities, connect with Simon here. 

Simon Mainwaring is a bestselling author, keynote speaker, thought leader, podcast host, and business columnist, and founder of MAIN Advisory, LLC.

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