At Crafty Counsel, we regularly focus on getting to know a member of our in-house legal community. This week we speak to General Counsel Sebastian Goldsmith, from Medigold Health, ​​which is a leading occupational health and wellbeing service provider in the UK. 

Seb is a member of Lean Legal, our group for sole counsel or those working in smaller legal teams, which meets regularly for virtual and in-person events.

Community Spotlight article with Sebastian Goldsmith, General Counsel for Medigold Health


Seb started as an Investment Funds solicitor at Nabarro LLP, and after a period at Latham & Watkins, he went in-house to IFM Investors. Six years after qualifying though, he started feeling a bit pigeonholed in this specialist field.

Then, an opportunity to become General Counsel arose around his family dinner table…

Seb’s father, Dr Mike Goldsmith, founded Medigold Health in 1998. His brother, Alex, left the City to join the company in 2006 and became the CEO in 2014. The company has grown from a staff of 50 when Alex joined, to 650 today. It was named one of 1,000 Companies to Inspire Britain by the London Stock Exchange for three successive years since 2017. Having reached that size, Medigold Health needed its own legal department. 

It was perfect timing, Seb was keen to move his young family from London to Northamptonshire. In March 2020, at the start of the Covid19 pandemic, he started setting up Medigold Health’s legal function.  

“Probably only now am I really enjoying my legal career,” he admits.

Adapting to a new industry and a new role

 “What I aim to do is to alleviate some of the pain points that people have experienced before, where they didn’t quite know where something should fit.” He’s had good responses since he started the job. “Sometimes it’s about process and implementing common sense solutions to make sure people are doing the right thing at the right time,” he says.

Although Seb likes getting exposure to what’s happening on the operational and finance side of the business as General Counsel, he hopes to expand his legal team at some point so that he can focus more on the high-level and strategic part of his role and spend less time on the “minutiae” that can sometimes be involved in routine legal work. Right now, he is the only member of the legal function, with colleagues in compliance, data protection and ESG reporting to him.

“As a small legal team, the resource is the hardest thing to adapt to. Not only do you have the day-to-day legal work but you also have to build a function,” he says.

Talent and Hobbies

Seb has always had creative tendencies, having been into creative writing when younger – a skill which he feels is not particularly well fed in a legal career. He considers the irony that although he felt out of place as a corporate lawyer living in East London, since moving North he has become a bit of an accidental hipster by falling into the stereotypes of barbecue, speciality coffee and big beards.

Since he started working at Medigold Health in 2020, he’s been living in Northamptonshire with his wife and two children. His (“now thriving and feisty”) two-year-old daughter was born seven weeks premature on the day the family moved from London (“which was a tad traumatic”) and he also has a “very funny” four-year-old son. He loves working from home because it allows him to spend more time with his family. 

His other passions when family life allows are video games, Arsenal FC (where he holds season tickets on the halfway line), Northampton Saints rugby, and playing and watching cricket.

Neurodiversity in the workplace 

After unexpectedly failing a couple of exams at law school, Seb found out that he was dyslexic. He was offered support and adjustments from the university after his diagnosis, and was able to retake the exams on a computer. 

“What I struggled with was processing speed, so my brain just didn’t work as quickly as some people’s. It’s quite quick on some stuff but sometimes when I really need to think something through,” he explains, “I run out of memory and then I have to start over again.”

Seb thinks the way lawyers are tested doesn’t fit everyone and there should be different options for people to prove they are capable of practicing law. “People who are more analytical don’t necessarily respond well to that kind of pressure.”

“How can you prove that someone is a decent lawyer by testing who can retain the most information over a 24-hour period? I appreciate I’m railing against the entire education industry there.”

Over the past few years, Seb became interested in how other people are dealing with being dyslexic. “Far more people are talking about it on LinkedIn now as a ‘dyslexic thinking skill’ which is fantastic because I definitely think in a different way than neurotypical people – and that’s an advantage.” He thinks neurodiversity should be celebrated.

“I do think the legal industry has some way to go in terms of inclusivity,” he says. He thinks the legal billing construct of ‘billable hours’ is a major barrier for neurodiverse people in the industry. “I think we should be paying for outcome-based work rather than pay by the hour anyway.”

What is it like working at a family business?

“The business started small and we still have a family ethos,” he says. But Seb wouldn’t quite compare it to being anything like the TV series Succession! Even though his brother, the CEO, is a best mate, they don’t always interact much during the workday. Instead, Seb reports to the company’s Chief Financial Officer (CFO), Eliot Caulton, to ensure healthy boundaries between family life and business. They work closely together, along with David Collis, the Commercial Director.

What is the biggest challenge you face in your job? 

Resource is the biggest challenge when you’re running a lean legal team, in Seb’s experience. “There are so many things I want to do that would make the business more efficient but you can’t implement them all” when dealing with “day-to-day” lower-value legal tasks or without an appropriate level of spend. 

The best decision Seb says he made in terms of resourcing was installing a full-time Data Protection Officer (DPO) and Compliance Associate Director, Isobel Watkins.

He is strategic about how he spends his resources; and is looking at different Legal Matter Management software platforms currently.  But, he is careful about adopting the wrong legal tech or too hastily. “It all depends on what the return on investment is.”

How has tech made a difference in your work?

One of the first things he did was source and implement a Contract Lifecycle Management (CLM) platform, Ironclad, which has been a great success but a steep learning curve for a sole counsel without legal ops support.

Before, the company’s contracts were kept as PDFs, signed with scanned signatures or images, and saved to a letter drive. “But when you get to the number of clients that we do, that’s not the best thing to do,” he says.  

He explains that the software turns their contract templates into conditional templates. The business users, such as Sales, can self-serve and the appropriate drafting will be inserted depending on their/the client’s responses. “Now we can fire through the agreements that we have with clients, the sales team can run that themselves, it goes to the commercial team to review and goes off for execution and sits in a repository where we now have all of the metadata.”

It took Seb almost nine months to set the system up properly (although he notes that was far more down to his lack of capacity than anything on Ironclad’s side).

“I can totally see now how you have an entire industry of legal ops, who come and do it for you,” Seb says ​​small medium-sized enterprises (SMEs) don’t often have that kind of capital to spend on legal operations. “It was hard enough for me to convince people that I should have a job here!” he laughs.

What is one of the best pieces of advice you have received and still use?

“Good enough”: is a mantra he repeats daily. Seb thinks lawyers tend to be perfectionists and are not very good at self-reflection or managing imposter syndrome. He believes that, particularly in-house, this search for perfect output can be counterproductive.

“You just end up in a mire of overthinking,” he says. “Just say: ‘it’s good enough and move on to the next thing.”