Having spent time working in private practice and as general counsel in the media industries, Gregor has broad experience of advising clients concerning the acquisition, production, licensing and distribution of content on media networks and platforms. He regularly advises companies that are involved in the distribution and sale of digital content, including digital music, video and gaming services, social networks, online retailers, aggregators, network and platform owners and search engines, regarding their arrangements with content owners and consumers. He also advises content owners and producers concerning the protection and exploitation of their intellectual property rights. His clients include computer game companies, film and television production houses, record labels, music publishers and advertisers. He also represents international celebrities and emerging talent.

Due to Gregor’s experience of negotiating and advising on cutting-edge digital content arrangements, clients often ask him to help formulate strategies that align with the developing body of laws relating to digital media. In recent years, he has worked with disruptors and innovators in the fields of social media, virtual and augmented reality and immersive experiences. Early stage companies often seek his advice concerning how best to leverage their technology and grow quickly in a fast-changing global environment, whilst traditional media companies work with him to adapt their approach towards younger, digital audiences.

In addition to counselling clients and facilitating transactions, Gregor is often engaged where there is a dispute; particularly in relation to exploitation rights. He also provides guidance in relation to information technology and related matters, including artificial intelligence, the development and implementation of systems and software and the governance of platform environments.

The Legal 500 has described Gregor as a "digital carriage superstar", whilst Chambers and Partners has rated him consistently in the Tier 1 of advisors in his sector, recognising his knowledge of digital music copyright issues and "unrivalled experience in the market". The International Who’s Who of Sports and Entertainment lawyers has described Gregor’s digital media practice as “second to none”.

In acknowledgement of his work in the sector, Gregor has been listed in numerous publications, including being one of the ‘Top 100 Most Influential People in Digital Media’ in Wired Magazine. He has also been featured in Music Week as one of the leaders of the Legal Team of the Year, as well as the ‘TechCity Insider 100’ list. He is a member of the Advisory Panel for the UK Government’s ‘Future Fifty’ programme for high-growth companies, and sits the Committee of the Internet and Media Leadership Group of the Prince’s Trust charity. Gregor also holds non-executive advisory roles in start-up companies from time to time.