Glenn Wilson: Backing Himself — Building Digital Auto Finance in NZ and Australia
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Glenn is the Co-Founder of Simplify Holdings International, a company specialising in personal and automotive finance across New Zealand and Australia. Ten years ago, Glenn and his team spotted a gap in the New Zealand market—limited consumer finance options and an almost non-existent online experience—and built Simplify to solve it.
Today, over 17,000 customers have used Simplify, and the business is on track to write over $150 million in finance volume this financial year. Glenn now plays a more strategic role in the group while the day-to-day is led by the team.
In our conversation we talk about Glenn’s foundations: growing up just outside Melbourne, Australia, being told by a teacher at 16 that he’d prefer it if Glenn left school, and how he turned that moment into fuel. We revisit his early career in IT, leading teams older than him, and the leadership lesson that it’s more important to be respected than liked.
We explore his move to BMW Australia, starting in customer service, building relationships across the organisation, and the practical value of curiosity. We discuss the impact of losing his mum, a period of travel and reflection, and the shift from finance broking as a sole operator to deciding—after a pivotal Tony Robbins event in Los Angeles—to build a bigger business.
We then trace the path to Simplify: seeing the New Zealand opportunity, starting small, persevering through perceptions of being “too Australian,” growing a distributed team across NZ and Australia, installing a CEO, and stepping into a strategic role while keeping close to the team and partners.
Connect with Glenn
Website
About Andy
I’m a business leader, coach, and the creator of the Fulfilling Performance framework—designed to help people bring more of themselves to what they do and experience greater fulfilment and performance as a result.
Over the past 25+ years, I’ve led and developed businesses including Alphabet UK, BMW Financial Services in the UK, Singapore, and New Zealand, and Tesla Financial Services UK. Alongside this, I’ve coached individuals and facilitated leadership development programmes in 17 countries across Asia, Europe, and North America.
In 2016, I founded Aquilae to support leaders and teams in the mobility sector and beyond. Through workshops, coaching, and peer mentoring, we enable high performance that’s also fulfilling—for individuals, teams, and organisations.
I’m also the host of CAREER-VIEW MIRROR, where I share the life and career journeys of key players in the automotive and mobility world to surface insights leaders can apply in their own context.
Learn more about Fulfilling Performance
Check out Release the Handbrake! The Fulfilling Performance Hub
Connect with Andy
LinkedIn: Andy Follows
Email: cvm@aquilae.co.uk
Join a peer mentoring team: Aquilae Academy
Thank you to our sponsors:
ASKE Consulting
Email: hello@askeconsulting.co.uk
Aquilae
Email: cvm@aquilae.co.uk
Episode Directory on Instagram @careerviewmirror
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Episode recorded on 23 October, 2025.