Howard Gray
Seeking the groove.
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Advisory & Coaching

The space between vision and execution is where most ventures stall. I help founders, executives, and organizations bridge that gap - turning uncertainty into strategy, ideas into systems, and challenges into competitive advantages.

Whether you're scaling a venture, expanding into new markets, or transforming how your team learns and works, the right guidance at the right time changes everything.

I'm a strategist, producer and educator who's built ventures across continents and guided Fortune 100 companies and creative entrepreneurs through transformation.

How I can help

1) Strategic Coaching for Creative Founders

Strategic clarity, positioning, and leadership development for creative entrepreneurs navigating growth and transitions. As an ICF-certified professional coach and 3x founder, I bring both structured methodologies and lived experience of building and scaling creative ventures.

Best for: Founders and creative executives ready to level up their strategy, positioning, and leadership presence.

Focus: Big-picture clarity, venture scaling, positioning strategy, and sustainable growth systems.

Working together, we'll help you clarify your positioning, transform ideas into viable ventures, master your storytelling, navigate leadership transitions, and overcome creative resistance.

→ Learn more about coaching programs

2) Learning Innovation Advisory

Future-focused consulting for organizations ready to transform how they develop talent and engage teams. Drawing from 300+ workshops delivered for Fortune 100 companies and experience designing programs for clients including EY, Publicis Groupe, and NYC.gov, I create learning experiences that drive real behavior change.

What I offer:

  • Next-generation learning program design
  • Workshop facilitation and team development
  • Immersive, scenario-based learning experiences, powered by Wavetable’s proprietary Involver platform
  • Educational technology strategy and implementation

Best for: Organizations in any industry moving beyond traditional training toward experiential, engaging learning that drives real behavior change.

3) Market Expansion for Founders

Strategic guidance for companies expanding between US and European markets, drawing from lived experience building ventures in the UK and scaling in the US. Having worked as a talent agent across 60+ countries, living and working in the US since 2017, and serving on SXSW's international advisory board, I understand both the strategic and cultural realities of international growth.

What I offer:

  • US↔Europe expansion strategy and cultural positioning
  • Go-to-market planning for international markets
  • Regulatory guidance and operational setup
  • Partnership development and market entry

Best for: Creative founders and growing companies ready to scale internationally but needing someone who's navigated the cultural, legal, and strategic realities firsthand.

As a taste of my thinking and approach, read my guide to Making it in America >

4) AI Integration & Workflow Optimization

Practical AI adoption for creative teams and organizations, focused on enhancing human creativity rather than replacing it. Having led AI/ML classes and workshops for hundreds of Fortune 500 executives and working hands-on with creative AI tools on a daily basis, I help organizations integrate AI strategically without losing their human edge.

What I offer:

  • Creative workflow assessment and AI tool integration
  • Team training on AI tools for content, design, strategy, and operations
  • Strategic AI adoption roadmaps for any organization looking to integrate AI thoughtfully
  • Hands-on prototyping and implementation support

Best for: Teams and organizations wanting to leverage AI strategically without losing their human edge.

What makes this different

  • I've been in nearly every seat at the table. Entrepreneur, freelancer, consultant, team leader. I've built ventures in the UK, scaled teams across continents, and worked with everyone from Fortune 100s to creative startups. This isn't just theory - it's lived experience.
  • I translate between worlds. Where pop culture meets business strategy. Where creativity meets systems thinking. Where bold ideas become practical moves.
  • I think deeply, then do the work. With hundreds of published articles, frameworks, and content across learning innovation, international expansion, and creative strategy, I bring both intellectual rigor and practical application to every engagement.
  • I focus on transformation, not information. Through hands-on co-development, strategic frameworks, and real-world application, we create sustainable change that sticks.

Ready to move forward?