Brand Forward: Scaling, Strategy & Success

About this episode

Jesse and Simon Littlewood discuss the journey of scaling a business and the strategic decisions involved in evolving a brand.

In this episode, Jesse sits down with Simon Littlewood from Estu Global to explore the journey of scaling a business, evolving a brand, and making strategic decisions for long-term impact . Simon shares insights into how his organisation has navigated growth, from engaging diverse communities and crossing cultural borders to securing large contracts and fostering meaningful partnerships. The conversation delves into the challenges of rebranding and positioning , discussing how a brand must stretch and adapt as it grows while maintaining its core identity. Simon also reflects on the importance of strategic planning , balancing structured and informal decision-making processes, and ensuring alignment between business values and the partners they choose to work with.

People in this episode

Host: Jesse

Guest: Simon Littlewood

Topics covered

• scaling a business
• branding
• strategic planning
• cultural diversity
• partnerships

Keywords

• business growth
• rebranding
• strategic decisions
• community engagement
• cultural borders

Mentioned in this episode

Organizations: Estu Global

More episodes of The B Word

• Branding in the age of LLM search: Engagement in an unbranded space · December 1, 2025 · 31 min
• Branding in the age of LLM search: Engagement in an unbranded space · November 19, 2025 · 1 min
• Tech Punks and Tardigrades: The Human Side of B2B Tech Branding · November 3, 2025 · 37 min
• Tech Punks and Tardigrades: The Human Side of B2B Tech Branding · November 3, 2025 · 2 min
• The Power of a Name: Navigating Change, Creativity, and Unpopular Decisions! · February 4, 2025 · 32 min
• Making commercial road transport clean, fair and efficient. · July 30, 2024 · 34 min