Diary of an Insurer: Staysure’s Finn Walsh

Diary of an insurer logo

Finn Walsh, CEO of Staysure, catches up with the provider's founders, aims to put the “sure” in travel insurance, goes to the gym and manages to read his son a quick story before bedtime.

Finn Walsh


After catching up on emails on the train journey to work, I grab a coffee enroute and settle in for a busy day. The week starts off in our London office where I often catch up with my leadership team to ensure all areas of the business remain on track and optimised for the week ahead. 

It is an exciting time for Staysure as we have a lot of new senior hires coming into the business and I am looking forward to meeting some of those who I will be interviewing later this morning. 

Part of my vision as the new CEO is to expand our knowledge and expertise with new members joining and help drive the business forward, but I am immensely proud of the broad range of dynamic individuals working here and what we have already achieved. 

After two promising interviews I take a quick break for lunch before heading straight into our weekly strategy meeting. 

The business is in a period of transformation, so these meetings are important to ensure we invest our time and efforts in the right areas now to ensure we excel in the coming months and years ahead. The main aim is to set the tone and expectations to meet our growth plans and keep my team focused and on track each week. 

I end the day catching up with emails and reading plans and reports before heading home.



Back in the London office today, but I am up a little earlier to squeeze in some quality breakfast time with my partner and son before heading off to work. I check emails on my commute, and its straight into the Tuesday trading meeting to review all aspects of business performance. 

This is followed by some preparation work before we hold the monthly companywide Town Hall meeting where we share ideas and communicate the business strategies to the wider teams. 

With so many changes having recently been made and new announcements to the leadership team, this meeting is important to share my vision for the brands and the new structure. It also gives everyone the opportunity to ask questions and provide recommendations for improvements across the business. 

In the afternoon, we have our digital transformation meeting. One of my priorities is making Staysure Group an Insurtech business of the future, with a digital first approach delivering a streamlined process across the brands.  

Bringing the team together to discuss the changes, bounce ideas back and forth, and check on progress is essential to make sure the process runs as smoothly as possible and provides the best outcome for our customers.

After a busy day, I hit the gym to reset my mind and let off a little steam ensuring I can get a good night’s rest. 


coffee meeting

It is an early drive to our Northampton headquarters today so no time to check emails until I arrive. 

With our new Staysure advertising campaign recently debuting after Christmas, brand planning and media performance has been another of my priorities. 

Today I have a meeting to check in on how the campaign is performing with the brand marketing team, and allow time to discuss the brand aims and priorities for the rest of the year.

The new campaign is about putting the “sure” in travel insurance, so it is essential we also keep an eye on our latest Trustpilot ratings to make sure our customer service remains at an exceptional standard.

The claims team are an integral part of that service as they also manage relationships with our underwriting partners. I like to check in with them when in HQ, to get a real-time read on how our customers are feeling and their experiences during a claim. It is also a great way of spotting any issues on the horizon and ensuring we can address them head on.

I often get home late from the Northampton office, but tonight I just managed to catch my son and read him a quick story before his bedtime.



Back to HQ today, Thursdays are always a big day because I have my weekly catch up with Ryan Howsam, Staysure’s founder. 

Ryan is an ideas man and being in touch with him regularly is crucial in shaping the future of the group’s brands. 

Following this, we have our leadership team meeting to discuss a wide range of topics across the business and I can bring Ryan’s latest thoughts and vision into those discussions. 

After a quick bite to eat in our canteen, I am looking forward to catching up with Lindsey Howsam over a coffee.  

As co-founder and Ryan’s sister, Lindsey is invested in making sure our customers are always at the heart of everything we do and that our employees are thriving in their roles. 

Evolving our company culture is a high priority and she gives employees the opportunities to share ideas and have a voice. Lindsey is a people person and really champions our workforce and the needs of our customers.

From there, I meet with our head of product and growth leaders to flesh out the new and innovative ideas on the table. As a leading provider, we are extremely focused on developing new and dynamic products and services to benefit our existing customers and those that will appeal to new audiences, so I always enjoy these sessions.

The day has flown by but has been very productive.  The drive home allows me time to reflect on all the conversations and great ideas that have been shared but also allows me the chance to unwind.


Swimming pool diversity

I usually end the week working from home on Fridays with more of a personal day catching up with emails I may have missed during the week and making sure everything is wrapped up ahead of the weekend. 

It also allows time to catch up with others across the business who may reach out to me and want to discuss something. 

It is important to reflect at the end of a busy week, so I always try and take time to look back and assess what went well, and what we can improve on going forward. It is a useful and mindful exercise that helps me be better and prepare for the following week.  

Friday evening is usually a gym session if I have the energy, followed by a family dinner, a nice bottle of wine and a good film to momentarily switch off.  

Tomorrow I will spend some quality time with my son as we love to go swimming on Saturday mornings where he takes great pleasure in fooling around trying to drown me.

Only users who have a paid subscription or are part of a corporate subscription are able to print or copy content.

To access these options, along with all other subscription benefits, please contact info@postonline.co.uk or view our subscription options here: http://subscriptions.postonline.co.uk/subscribe

You are currently unable to copy this content. Please contact info@postonline.co.uk to find out more.

Big Interview: Andy Bord, Flood Re

On his last day as Flood Re CEO, Andy Bord catches up with Emma Ann Hughes on how the scheme will end in 2039, his pride around Build Back Better, plus why Labour’s promise to build more homes must be accompanied by a robust planning framework.

Most read articles loading...

You need to sign in to use this feature. If you don’t have an Insurance Post account, please register for a trial.

Sign in
You are currently on corporate access.

To use this feature you will need an individual account. If you have one already please sign in.

Sign in.

Alternatively you can request an individual account here