Caroline Sherry, Hostelworld CFO, On Being A Female Leader - The Gloss Magazine

Caroline Sherry, Hostelworld CFO, On Being A Female Leader

Hostelworld, the global hostel-focused online booking platform, was founded in 1999 and headquartered in Dublin. Hostelworld has a team of 230 people working across its Dublin, London, Porto, Shanghai and Sydney offices, and is listed on Euronext Dublin with a market capitalisation of €180 million as of May 2025.

How did you come to be in your current role? What was your journey to it?

I joined Hostelworld in 2019, initially as Group Financial Controller before being appointed Chief Financial Officer and joining the board in 2020. I’m a chartered accountant and trained at PwC. I have worked across various sectors throughout my career; however, the role in Hostelworld was a compelling opportunity as it is such a unique company. Hostelworld is an Irish PLC technology company in the travel sector, with a strong reputation and clear growth ambitions. I also liked its size and scale, and knew it would offer me the opportunity to broaden my experience in many areas of the business.

What do you love about your role? What aspects of it do you find inspiring?

I genuinely love the variety. My role is broad and encompasses many interesting areas aside from core finance aspects. I enjoy my work with our ESG SteerCo, which I chair, as well as being a member of the Balance for Better Business Review Group and the 30% Club. I always enjoy meeting shareholders and talking to the investment community about the business – I invariably learn something from this external perspective. I find the people I work with really inspiring; a highly motivated, talented group of people working on interesting projects that deliver great outcomes for our customers.

What has been the biggest challenge to date?

COVID was certainly one of the most challenging times. Our business practically shuttered overnight, a situation that persisted for an almost two-year period. We had to undertake some major changes in the business, reorganising our organisational structure and cost base, managing our liquidity and cash burn over a significant period of time. Our shareholders, suppliers and partners were incredibly supportive. We raised equity, we raised debt, we refinanced debt and we’re now entirely debt-free. A huge accomplishment and professionally very rewarding, particularly for a small finance team.

Are you confident about your retirement? Do you feel like you have got enough squared away?

It’s something I’ve become more proactive managing in the past year. I’ve always paid into a pension, but more recently I’ve focused on the management of my pension, looking at different plan options and pension top-ups. I want to take a more active approach, rather than passively paying in each month and hoping it all comes together when I need it! I feel like I’m on track.

Do you follow the stock market, or have you got any plans to invest?

Following the market is a key part of my role and I’ve made it part of my daily routine at this stage. I hold shares, but I’m definitely more of a saver than speculatively playing the market.

What’s the best money advice you’ve ever received?

I remember when I bought my first house, and I was negotiating the sales price. I was the only bidder (the house was in very bad condition) and my dad advised me to hold firm on the price I offered; he told me that ‘it’s better in your pocket than in theirs’. We subsequently completed at my offer price. His words stuck with me.

READ MORE: Kim O’Sullivan, Founder of Brow Aid, On Being A Female Leader

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