MEET THE MAESTRO INTERVIEW

PENELOPE: Innovation, Change & Transformation Global Execuitive

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At Maestro, we know there’s more to life than work. In our “Meet the Maestro” series, we peek beyond the CV to discover what makes our Maestros tick.

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Penelope is a seasoned startup founder, mentor, and trusted advisor with over 20 years of global experience in innovation, product development and business transformation. As a dynamic executive, she brings a unique blend of strategic insight and hands-on execution to the table. Penelope’s superpowers lie in her ability to help individuals and organisations design work that truly works for them—work that is purposeful, adaptive and aligned with their values and goals. Whether she’s coaching early-stage founders or advising large enterprises, Penelope’s impact is rooted in her talent for unlocking potential, navigating complexity and turning vision into value.

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1. Tell us about a career highlight to date…

Production Manager of the Sydney 2000 Olympics, The Olympic Journey a processional parade and 3 hours of public entertainment over 26 weekends, designed to generate enthusiasm and sell tickets for the Olympics. 

2. Talk us through an unusual career choice you’ve made along the way…

I started in Marketing and Product, moved to Digital tech and Innovation in financial services, media and legal, and now work in a portfolio career aligned to the seasons I’ve created called 6:3:3 which sees me do interim exec work, create books, products and communities, and travel. 

3. When you were little, what did you want to be when you grew up?

For a long time I wanted to be a fashion designer, then a diplomat, then a spy. I explored each of these careers during and after university. 

4. What are your passions outside of work and how do you make time for them?

I schedule my year, including time for my hobbies and passions. I travel, paint and volunteer with a couple of charities. 

5. If you could instantly master any skill or hobby, what would it be and why?

Archery. We saw it at the Paris Olympics and loved it. I’m ok but not great and would love to be much better.

6. What’s a personal value or belief that guides the way you live your life?

I believe no, no, no, no eventually gets to yes, a guiding principle to ensure I keep going when I have a vision or a goal. 

7. What’s a challenge you’ve overcome outside of work that shaped you?

I’m not sure you ever overcome grief but I’ve had several close relatives and friends die in the past few years. The impact has been to live life more intentionally. 

8. What do you think your job will look like in 10 years time? 

In 10 years’ time I’m likely to working in a similar way to today, pursuing several diverse income streams, Board roles, coaching and travelling.

9. If you could travel anywhere in the world tomorrow, where would you go and what would you do?

I have a plan for the next 10 years of travel. So next on the list is walking some of the Camino near Quercy in France after I complete the next Writing and Creativity Retreat in France in September. Then, Taiwan. 

10. What does success look like to you?

This is an easy one. Success looks like having choice, choice in how I spend my time, my energy, who I help and how I make money.