Our leadership team

Rachael Greaves

Chief Executive Officer

Rachael has been instrumental to the development of Castlepoint and is responsible for scaling the business to meet its global ambitions and fundraising.

She is a records and information management and cyber security thought leader and designed the Castlepoint command and control product. Rachael has consulted on large-scale records, security and audit projects in government and regulated industries with complex integrated environments. She developed Castlepoint in response to the tension seen in organisations between compliance, usability, sustainability and cost.

Rachael is a Certified Information Professional (CIP), Certified Information Systems Auditor (CISA), Certified Information Security Manager (CISM), Certified Data Privacy Systems Engineer (CDPSE), and is certified in project, change, and records management.

Rachael has a cultural anthropology and linguistics background and speaks English, Latin, French, Spanish and Italian and she has a truck licence.

Gavin McKay

Chief Technology Officer

Gavin has been instrumental to the development of Castlepoint and is responsible for technology and product architecture.
He has 30 years of experience in a variety of senior roles in IT, Cloud, AI and integration and has worked with Microsoft SharePoint for over 10 years, designing solutions for government and private sector companies. Gavin is skilled in networking infrastructure, server configuration, enterprise storage, enterprise search, collaboration technologies, web and application development, and security management.

Gavin is a Microsoft Certified Professional in SharePoint 2010 and 2013, a Certified Information Manager, certified in PRINCE2 (Foundation), has a BA in Computing Studies from the University of Canberra and has a current National Security clearance rated to Secret.
During COVID lockdown, Gavin joined the many millions of people that taught themselves how to make sourdough bread.

Charles Pittar

GM, Growth & Customer Success

At Castlepoint, Charles is responsible for driving business growth and ensuring we deliver amazing customer experiences.
He is a globally recognised senior executive with over 20 years’ experience in technology, strategy and leadership roles at some of the world’s most respected public companies – including Macquarie Group, Microsoft, Goldman Sachs – as well as various startups.
He began his career programming at Microsoft and went on to drive and optimise major infrastructure footprints, cloud computing migration, information security solutions, secure collaboration technology implementations and SaaS technology company leadership.
If you need help for a trivia night, Charles can answer ANY question about the Rolling Stones.

Hugh Macdermott

GM, Product & Technology

At Castlepoint, Hugh is responsible for managing the Technology team and ensuring the Castlepoint product is delivering high quality updates to our customers.  He also manages the Product and Technology strategy and roadmap.

Hugh has over 20 years’ experience in senior product roles in the UK and Australia, including AOL, BSYkB, Guardian News, Lonely Planet, ANZ, NewsCorp and OFX and specialises in helping businesses align their product strategy with their business goals..

Hugh has a BA in Computing Studies from the University of Canberra, a Masters of Business & Technology from UNSW and is a Members of the Australian Institute of Company Directors. Oh, and Jeg snakker litt Norsk, men ikke bra (He speaks a little Norwegian but not well).

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