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Caroline O’Grady

Partner, Coote O'Grady Ltd.



Following qualification as a UK Solicitor and several years as a Law Firm Panel Director at AIG, Caroline has spent the last 10 years working in legal operations and legal technology. She has worked to build a bespoke services package specific to the European market, while still servicing global clients in all areas of legal spend. Her focus in recent years has been the development of proprietary legal technology, bringing her knowledge of the market into the tech she designs.  

Along with her co-founder, she has built a legal services business, whose client list includes global insurers, banks, one of the largest global automotive companies, as well as public sector organisations. These clients were all attracted to the unique tech / services combination offered by Coote O’Grady – the products bring the best of technological capability coupled with Caroline’s comprehensive knowledge of the markets she works in.

Before developing her own technology, Caroline helped to design and implement various legal tech products for global organisations.

Contribution to Legal Tech

Caroline has designed a bespoke invoice review technology, delivering legal invoice review, savings tracking and customer dashboard services (coupled with the services element of the Coote O’Grady invoice review team) – this gives the end-to-end service of data collection, human-led legal invoice review, and savings tracking. She also designed an insurance-specific portal for collection of key insurance law firm metrics, allowing insurers to performance manage their law firms, as well as use the data to drive general efficiencies and savings. This is a first-in-market product and supports a state-of-the-art performance management programme.

These products are in use within global Fortune 500 companies, saving their clients millions in legal spend.

In creating these products, Caroline and her co-founder have ensured they build a diverse and inclusive business, passionate about bringing women into the legal operations and technology space. She has coached and mentored women stepping into this sector, and ensured the business is constantly opening doors to those who have struggled in the past, most commonly working mothers. Gender diversity and equality is a cornerstone of Coote O’Grady, with over 80% of the staff being female. The company allow full flexibility in working patterns, remote working since its creation, and brings an open, family-friendly policy to working life, all while delivering a comprehensive and first-class service to global organisations.              

Coote O’Grady has grown over 60% this year alone, as a result of the services and products delivered by Caroline and the team.

Before this, Caroline was instrumental in the roll-out of various eBilling technology solutions both within the insurance and other sectors. She has niche experience in ensuring these products are tailored to the non-US market particularly.

Other Winners


Laura Fauqueur

(Freelance) Design Thinking Facilitator, Director of Masters in Legaltech at CEU IAM