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Diary of an Insurer: Rokstone’s Darren Guymer

Darren Guymer diary

Darren Guymer was hired as head of surety at Rokstone in June 2025. His working week sees him take a hands-on approach to building relationships with both carriers and brokers while also coaching his son’s under eight’s football team.

Monday

New week, new opportunities.  I’ve been building the Rokstone Surety division, leveraging my background as both broker and underwriter to define the opportunity for Rokstone – the types of bonds, clients, and areas of the market we want to target, negotiating with our carrier partner, devising product lines, setting our appetite and rating model, establishing an end-to-end bond issuance process, and defining our claims handling procedures.

It’s been a dream of mine to start a Surety business, and Rokstone has given me a huge opportunity and the support to achieve profitability as quickly as possible. Now that the groundwork is done, I’m getting stuck into writing business.

First on the agenda today is a new broker introduced construction client requiring a performance bond. A quick response and flexible approach are vital.  I complete my financial analysis, as well as the contract and bond wording review.  

Once I’m happy, we proceed to set the terms, draft the documentation, and get the indemnities negotiated and approved. A quick Teams call, and we can get this bond issued.

The rest of the day is spent answering emails, checking in with broker contacts, and putting meetings in the diary.  I end the day in the same way I do every Monday, playing a six aside game of football with my team.

Tuesday

I’m answering emails before dropping my children off at school.  I start by checking in with various internal stakeholders. 

Getting the Surety division up and running so quickly has been a collaborative process.  I get together with colleagues from across our underwriting services, bordereaux, and collection teams to check that all is on track and the process we defined is progressing as it should.

Next on the agenda is a Teams meeting with our carrier partner.  I keep in regular contact to help maintain trust and alignment.  

Now that we’re up and running and underwriting risks, I’m keen that we always keep one eye on the bigger picture.  Our long-term aim is to build a suite of 15 to 20 products across different sectors and bond types. 

The bond market has been tough this last few years, but new opportunities are emerging all the time, and we want to ensure that we have the backing to go after them.

After a day of answering emails and meetings, I take my son to his football training session.  Then it’s a quiet evening with the family.

Wednesday

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I’m back in my home office.  I am in the middle of a home renovation project, so once the kids are safely dropped at school, and I’ve made the builders a cup of tea, I join a call with Tom Donachie, underwriting portfolio manager at Rokstone.  

We catch-up weekly on progress both in terms of new opportunities and existing clients.  It’s great to have such strong buy-in and support from the senior team.

After answering a few emails, I join the monthly trading call.  This is when colleagues from across all of Rokstone’s commercial lines teams keep each other up to date with what’s happening across the business.  

I deliver a summary and management information report and chat to colleagues about potential synergies we can exploit to deliver more value to brokers.

After lunch, during which I grab a quick 20-minute ride out on my motorbike, I see that we have received a firm order.  

I review the wording with both the client and the beneficiary, and tweak as necessary to ensure we have a solution that suits everyone’s needs.  

Football

I then jump on a call with a couple of brokers about potential bond facilities and confirm a meeting in Surrey for Friday. 

My mantra is always to stay close to brokers and clients.  I ensure that I’m always available, responsive and consistent.

I end the day doing my other job – coaching my son’s under-eight football team. 

Thursday

I’m up at 5.30am to catch the 6.30am train to Rokstone’s London office today. Thursday is always a good day to be in the market.

I plan for an upcoming Rokstone ‘Lunch and Learn’ session.  I will be presenting to colleagues as part of a business-wide learning initiative.   

I meet up with a couple of brokers that we recently onboarded for lunch, then once back at my desk, I check-in on some potential clients that I connected with at The Manchester Builders Golf Day.

I’m back in Norwich in time for family dinner.  I need an early night as I’m up early for a meeting in Surrey tomorrow.

Friday

I am on the road at 6am. I spend most of the day at the client’s offices ahead of a large bond we’re issuing for a big long-term construction project.  

This is a great opportunity to meet with as many of the team as possible, and thereby keep building our relationship.

After a long drive home, I get set for a weekend of fun with my family. And yes, there will be a bit of football in the mix! 

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