MEET THE MAESTRO: Fractional Expert Sydney

Helen - IT Leader

At Maestro, we know there’s more to life than work. In fact, it’s the experiences, relationships and pursuits we have outside of work that can often give us an edge in what we do each day. We are kicking off an interview series called “Meet the Maestro” where we interview our Maestros and get an insight to who they really are and what makes them tick - beyond the CV.

As a seasoned IT leader with over a decade of experience, Helen specialises in helping scaling start-ups overcome delivery challenges and achieve rapid growth. Having lived in five countries and worked across seventeen, she brings a truly global perspective and a wealth of cross-industry insight, from consumer goods to manufacturing.

Certified in PRINCE2, ITIL 4, BRMP, and CBRM, Helen combines strategic vision with hands-on delivery expertise, guiding organisations from roadmap to business-as-usual. Passionate about innovation, she stays at the forefront of technology trends and her superpower lies in connecting the dots between siloed departments orchestrating the right discussions, with the right people, at the right time to unlock data-driven decision-making and accelerate outcomes.

Working remotely with fractional and project-based clients, Helen focuses on three key areas:

• Revive: Get stalled projects back on track with impartial advisory support, clear priorities and renewed momentum.
  
• Refine: Optimise project management frameworks, governance and processes to drive efficient, effective delivery.
  
• Rocket: Scale with confidence by building high-performing IT teams, designing IT roadmaps and navigating vendor RFPs seamlessly.
  

With Helen on your side, you don’t just manage IT change, you make it a catalyst for growth.

1. Tell us about a career highlight to date…

The best role I ever had wasn’t my most senior. But it shaped how I lead transformation to this day.

When Dyson created a new Business Partnering team in IT, I was chosen to lead for their Emerging Markets. That meant working across high-growth, high-ambiguity regions like Russia, India, Japan, Turkey, South Korea, and Singapore.

It wasn’t about perfect process or big frameworks.  It was about pace, nuance, and orchestration.

During this chapter, I further strengthen my superpower: orchestrating the right conversations, with the right people, at the right time.

Not just aligning on what to decide, but ensuring that someone actually made the decision, and that the business, tech, and ops teams could move forward, together.

Emerging markets don’t wait around for perfect solutions. They demand clarity, context, and creativity. Quickly.

That role showed me that continued transformation isn’t about more frameworks or more tools. It’s about becoming a decision-enabler in complex environments.

Years later, I still apply that exact principle in every fractional or project role I hold.

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

I fell into IT. Having completed a HR placement with IBM in their Diversity and Inclusion team, I was all set to return to their graduation scheme in a HR role. However, when there wasn’t a matching HR role, I was offered a software consulting role. 

I’m glad it turned out that way and if I had more exposure to technology when I was younger, the detail orientated, problem solving aspiring accountant may actually have had a career as a software developer. 

As it turns out, in my role today, I pull on my people skills through orchestrating conversations, stakeholder management and team building. I get to dive into detail when helping founders and c suite members make data driven decisions and I get to dive into technical details when reviewing solution designs and driving technical architecture decisions. 

I have no doubt what ever path I chose I would always end up at the intersect of people, process and tools. As I believe all three need to work together for success and therefore I work to understand all three.

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

An accountant, I excelled in maths and enjoyed the problem solving of algebra. I loved the black and white nature of accounting. 

I see this come through in my work today in how I thrive in problem solving and using data and facts to drive decisions and next steps.

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

Reading – I am part of a non fiction book club which meets on a monthly basis and I always have a fiction read on the go for quiet moments. A recent fiction read I enjoyed was ‘Butter’ by Asako Yuzuki, for it’s social commentary, being based in Japan (my favourite place in the world) and the focus on amazimg foods! 

Creativity – Whether it’s painting / drawing or through cooking/baking for my husband and I. I love being creative! 

Gaming – I enjoy playing games like Call of Duty and Street Fighter. I love the fast pace and ensuring I enter the right action at the right time – similar to what I do in the workplace! I’ll play Call of Duty with my husband in a morning, a more fun way to wake up my brain than caffeine!

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

I would master survival skills, so I had more skills in my arsenal to take me away from screens. Think foraging , hunting, first aid.

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

There is always more to learn, whether it is perfecting a skill or learning something totally new. 

It also means I don’t strive to be the best at everything, I strive to be the best at what I am good at, while learning more about areas I am developing and working with others / letting others lead where they excel.

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

I have been very privileged to live in 5 different countries. Moving countries is an amazing experience but it is also a challenge, no matter how many times you do it. 

Living and working in different cultures has shaped who I am as a person, from the food I eat, how I communicate and how I make decisions. 

It has especially shaped how quickly I can connect with a person or embed myself within a client’s organisation, and also the ease I have with contracts ending. This helps in my fractional/project based practice as I work knowing there will be an end point, so I embed my knowledge as I work with the client and ensure I add value asap.

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

The hype around AI will have been replaced with a new exciting technology. The new technology, as is the same for AI, is not going to be the silver bullet companies need to succeed. 

I will continue to work fractionally with scaling companies to help them revive, refine and rocket. Albeit, some of those discussions will be with AI agents and solutions will differ to those implemented today.

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

I would return to Japan. Having spent a lot of time working there, I have a massive appreciation for the culture and scenary. It’s my favourite place in the world. 

I would have a trip with zero work items and instead enjoy what Japan has to offer with my husband.

10. What does success look like to you?

Being able to choose the clients I work with while leaving enough energy for passion projects and family time.