Transforming Digital Growth for Insurance and Financial Professionals Across New Zealand and Australia
About Greg Dickson
You might say Greg Dickson wears a lot of hats, as a leading digital strategist, he’s the go-to fractional CTO and CMO at Gerrards Insurance Brokers (where they’ve made quite a name for themselves specialising in business insurance), and the creative force behind AiSearch.Marketing & Bizsure and Money Savers.
With over two decades of getting his hands dirty in financial services – including building and running several successful businesses back in the UK – Greg has become something of a legend among advisors, brokers, and service firms who are serious about dominating their market. And not just any domination – the ethical, sustainable kind that builds legacies rather than just quarterly profits.
What really sets Greg apart? He’s cracked the code on AI-driven content marketing, search engine optimization, marketing automation, and client acquisition strategies that actually work in the highly regulated worlds of insurance and finance. Trust me, that’s no small feat.
At Gerrards Insurance Brokers, Greg doesn’t just dabble – he orchestrates both the technology and marketing strategy, drawing on his vast experience to revolutionize operational efficiency, client acquisition systems, and digital innovation throughout the business insurance sector.
It’s a rare bird who can combine cutting-edge technology expertise with human-centered marketing and deep industry knowledge. Greg is that rare bird, and the results he delivers for his clients are nothing short of exceptional.
Philosophy & Approach
In today’s digital landscape – where everyone and their dog is fighting for attention – Greg firmly believes success comes down to four critical elements:
- Personalization at scale (because nobody wants to feel like just another number)
- Strategic trust-building content (that actually helps people, imagine that!)
- Operational efficiency through automation (working smarter, not harder)
- Mastery of AI-driven search ecosystems (staying ahead of the curve, not chasing it)
Greg’s work isn’t built on passing fads or flashy tactics. It’s deeply rooted in principles and strict compliance with regulatory frameworks set by bodies like the Financial Markets Authority (FMA), Reserve Bank of New Zealand (RBNZ), and Australian Prudential Regulation Authority (APRA).
As Greg often says over coffee with clients (he’s partial to a flat white, no sugar): “It’s not about reaching the most people. It’s about reaching the right people — at the right time, with the right message — and doing it better than anyone else.”
Areas of Expertise
SEO for Regulated Industries: Not your garden-variety search engine optimization. Greg specializes in strategies designed specifically for compliance-heavy industries like insurance, finance, and real estate – where one wrong word can mean regulatory headaches.
AI-Enhanced Lead Generation: Greg was leveraging AI platforms and semantic search strategies to deliver pre-qualified, exclusive leads back when most marketers were still trying to figure out what “AI” actually meant.
Content Marketing & Authority Building: Anyone can create content. Greg creates entire content ecosystems that position his clients as the obvious – sometimes only – choice in their market.
Sales Funnel and Conversion Optimization: Building automated systems that nurture, qualify, and convert prospects at scale isn’t rocket science… but it’s pretty close. Greg makes it look easy.
Marketing Automation Systems: While some people struggle to set up an email autoresponder, Greg is architecting complex systems using n8n, Make.com, Zapier, and full-stack CRM integration that practically print money for his clients.
Technology Leadership for Financial Firms: Providing CTO-level oversight of technology systems for insurance brokerages and financial advisory firms, helping them navigate the increasingly complex digital landscape.
Career Highlights
- Fractional CTO and CMO for Gerrards Insurance Brokers (specializing in business insurance across New Zealand) – where he’s helped transform a traditional brokerage into a digital-first powerhouse.
- Founder of AdvisorsContent.nz: Helping insurance advisors consistently generate ideal clients through SEO, content, and AI-enhanced strategies. One advisor reportedly said, “I went from chasing clients to turning them away in under six months.”
- Director of AiSearch.Marketing: Delivering cutting-edge AI Search optimization solutions to future-proof businesses in the AI-driven search era – back when most people thought “Bard” was just something Shakespeare was.
- Founder and Operator of Multiple Financial Services Businesses in the United Kingdom – learning the hard lessons so his clients don’t have to.
- Consultant to Over 100 Financial and Insurance Brands across New Zealand and Australia – each one with unique challenges that helped shape Greg’s comprehensive approach.
- Contributing Thought Leader to LinkedIn professional networks and insurance media platforms such as RiskInfo NZ – sharing insights that frequently go viral within industry circles.
Media & Thought Leadership
Greg’s strategies, methodologies, and success stories haven’t gone unnoticed. They’ve been featured or referenced by:
- LinkedIn Professional Community (where his posts regularly spark industry-wide conversations)
- RiskInfo NZ (Contributor)
- Private Advisory and Insurance Masterminds across New Zealand & UK
He doesn’t just keep up with emerging trends in AI search marketing, regulated industry content strategy, and digital transformation for insurance brokers – he helps define them.
A Personal Note from Greg
“The financial services world is changing — fast. The advisors, brokers, and firms that adapt to AI, personalization, and automation will dominate.
My mission is to help serious businesses not just survive this shift, but thrive, grow, and win — ethically, sustainably, and intelligently.
If you’re ready to build a digital growth machine that generates quality clients predictably, I’m ready to help.”
There was a time, not so long ago, when Greg was sitting across from a veteran insurance broker who insisted that “digital marketing doesn’t work in our industry.” Six months later, that same broker called Greg at 9 PM on a Friday, almost in tears, to thank him for the transformation in his business. “For the first time in 15 years,” he said, “I’m turning away clients because I can’t handle the volume.”