Diary of an Insurer: Staysure’s Simon McCulloch

Monday

I start the week with an early train into London and a quick catch-up on emails.  

I have a full day of meetings planned and will work from one of our flexible working hubs.  I grab a coffee for the journey and use the quiet time to look at the weekend’s trading numbers.  

The train journey is one of the rare moments I get to step away from the detail and think more about the bigger picture.

Once settled at my desk I dive into the steering committee that looks at our growth brands.  

It’s a lively session – checking progress, swapping ideas, and deciding how we’ll keep momentum across the group.  

Later, I sit down with one of our major business clients for a working session. Face-to-face, we delve into performance and map out the growth agenda we’ll tackle together over the coming months.

In the afternoon, I have a weekly catch-up with one of my direct reports, who leads our price comparison business.  

We review project delivery milestones and talk through performance. By the time I’m on my way home, my head’s still buzzing with conversations and ideas. 

I love to cycle, so put on my cycling gear and jump on the road bike for a short ride through the nearby villages which allows me to switch gears and clear my head after a full-on start to the week.

Tuesday

I’m in our Northampton head office. It’s a busy day on site – lots of colleagues choose Tuesdays for in-person work – so there’s an energy about the building and it’s a good day for quick catch-ups across the different teams.

Tuesday mornings are all about performance – first, a trading session on one of our core digital brands, then straight into the challenger brands steering committee. Here we focus on our progress of launching new propositions across alternative channels and review the status of our product development initiatives that are designed to help us reach and attract more customers in innovative ways.

By the afternoon, the pace shifts.  

Our market research agency shares fresh customer insights – this customer data sparks plenty of ideas about refinements that can be made across our products and services.  

I close the day in another trading meeting, this time focusing on our expat business, assessing current performance, ensuring our growth opportunities are on track and looking at how we can support more customers living overseas.

Wednesday

Midweek, I work from home. It’s a different rhythm but there’s still a packed schedule to get through.  

First up, aligning with the C-suite on mid-year reviews to make sure we’re recognising leadership fairly and consistently across the board.  

Then it’s back into trading mode with one of our business partners, reviewing performance and exploring opportunities that will refine and improve results.

A pre-lunch conversation with an external product provider about a potential growth initiative not only sparks immediate opportunities to execute but also lays further groundwork for some more longer-term innovations.

After a quick bite to eat, I catch-up with our marketing lead to review the current activity across both domestic and international markets.  

Our marketing is vital to driving our commercial success, so we are always evolving, reviewing, adapting our plans in a bid to stay ahead.  

My final meeting of the day is with our overseas insurance partner. This is an opportunity to dig into the underwriting and trading performance of our expat brand and explore new opportunities for expansion. 

As the day ends, it gives me a chance to respond to emails and prepare for the morning’s executive committee meeting. 

Tonight, I have a personal training session planned which allows me time to switch off and reset.

Thursday

I’m back at the Northampton office for the executive committee meeting. This is a full-day session where the C-suite comes together to review performance and activity across all brands, functions and markets.  

With such a broad mix of business units, channels and territories, it’s a vital forum for staying aligned and focused on our wider growth and transformation plans.

In the evening, the wider senior management team join us for drinks and snacks at the local pub.  

It’s a relaxed gathering on the sunny terrace and perfect for sharing key takeaways from the day and catching up face-to-face – it’s amazing how much alignment comes from these informal conversations over a drink.

Friday

Working from home again, the day begins with product development planning and market sizing.  

I relish these discussions as our product innovations are vital to support some of the early-stage ideas we’re shaping to meet evolving customer needs.   

I then join a regular compliance and risk session, which forms part of my senior management functions responsibilities and is key in helping me stay close to the operational detail while ensuring we are delivering consistently and responsibly for our customers.

Throughout mid-morning and into the afternoon I have one-to-ones with my direct reports to catch up on any issues and relay key discussions from the week.  

These are followed by a series of short, focused meetings to discuss our quote conversion improvement initiative and progress across our emerging price comparison website brands.   

The final meeting of the week is with our chief insurance officer about underwriting performance and pricing.

The rest of the afternoon is for tying up loose ends – emails, Teams messages, and getting the diary straight for the week ahead.  

Then, finally, it’s time to let the weekend in. For me, that usually starts with a long walk with my dog, Roscoe, where we usually finish at the village pub for a well-earned drink before heading home for dinner.