Our leadership team

Meet the Castlepoint Executive Team and general managers.

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.

She is a records and information management and cyber security thought leader and designed the Castlepoint command and control product.

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 wrote her thesis on the Pharsalia.

Gavin McKay

Chief Technology Officer

Gavin created the Castlepoint system and is responsible for technology and product architecture.


He has 35 years of experience in a variety of senior roles in IT, Cloud, AI and integration, 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.


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, and Goldman Sachs.

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).

Lyndal Hughson

GM, Operations

At Castlepoint, Lyndal is responsible for managing operations from staffing to procedures to project management.

Lyndal is an experienced business management professional with experience in diverse sectors including professional services, financial services, not-for-profit , community and cultural.

Her range of experience includes investment accounting and unit pricing, financial accounting, project management, vendor relationship management, government liaison and relationship management, compliance, IT management, funding applications, company secretarial, team management and product development.

Matthew Tribe

Chief Financial Officer

Matthew is a finance professional with extensive experience in fundraising, reporting, modelling, and systems implementation for growth-stage and mid-size companies. He has a Bachelor of Commerce from the University of NSW, and is a licenced Chartered Accountant (CP, CPA).

Interested in working with us? Find out more about joining Castlepoint.

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