Caleb Raywood

I started legal life as a shipping law barrister in London before moving to Dubai in 1998 and handling a broad range of corporate and commercial disputes, as well as non-contentious matters in private practice. Since then, I’ve held several General Counsel roles over more than a decade, reporting to CEOs and Board chairs, and have built up broad expertise across offshore energy services, commodities, payment systems and healthcare. Much of that work has been performed in distressed (and almost always stressful) situations.

My last deal as an in-house lawyer was the 2023 sale of a high value, specialised vessel to a state-owned entity that touched the fast-evolving sanctions regimes of seven jurisdictions. The risk of a breach of sanctions was so severe that we couldn’t get a law firm to help and banks were far from keen to be involved. So I was very much left to my own devices playing the roles of sole negotiator, legal counsel and board of directors.

After successfully closing that transaction (involving trips to the Cayman Islands, Tokyo and Istanbul and settling over 150 documents), nothing was going to come close to matching that experience. It was time to recalibrate and look for something new.

What I love about working with Peerpoint is how it has opened up a new world of opportunities. Being somewhat introverted, I didn’t spend nearly enough time building a client base in private practice nor an extensive professional network while in-house. But fortunately, this is Peerpoint’s strength. They provide support with my marketing and business development and, thanks to their law firm backing, brand me with a highly valued badge of endorsement.

A&O Shearman’s deep connections with great companies mean that the opportunities are fascinating and almost impossible otherwise to access. As the partners have often been providing services for many years, they have great insights to share on the company.

I’d describe myself as a specialist at being a generalist – if my career was an Olympic sport, it would be the decathlon. A consulting practice suits that disposition very well because no two assignments are ever the same.

I’m typically supporting or stepping in for the General Counsel in roles that are as much about project management, leadership and engagement as they are about law with tasks as varied as leading on one of the UAE’s largest business interruption claims arising out of the 2024 Dubai floods to developing playbooks for a very large organisation to recover bad debt. With my seniority, I’m now getting a particular kick from supporting junior members of the teams I work with, setting them up to understand and exceed the GC’s expectations, as much as I get satisfaction from rolling up my sleeves on conventional lawyering.

There are certainly different rules of the road to follow when you become a legal consultant. My advice would be to stay laser-focused on what the client is asking for (ensuring the goals are clear from the outset and reviewed regularly) and stick to the script: for example, unless specifically asked, you are not there to build a relationship with the C-suite which might risk disintermediating the GC or other senior counsel.

At the same time, if you come across a challenging character on the client team, there’s no need to become defensive or burn too many calories trying to get on their right side; you can smile and walk away, knowing that your paths will not be crossing indefinitely.

I was ready for a new opportunity when I became a legal consultant; I have always loved the variety of work a legal practice can bring, and you get no greater variety than not quite knowing where you will be six months from now.