60 Seconds With

“To me, success is financial freedom” – 60 seconds with tech entrepreneur Ciara Crossan, founder of WedPro

By Business & Finance
30 January 2024
Ciara Crossan, CEO of WeddingDates, smiling in a professional portrait
Pictured: Ciara Crossan, Founder and CEO of WedPro, a Cork-based technology company.

Ciara Crossan is founder of WedPro technology and CEO of WeddingDates, a Cork-based technology company that supplies marketing software enabling wedding venues in Ireland and the UK to manage and maximise conversions from enquiry to booking. 

What was your first job? 

My very first job was selling knives door to door in Massachusetts.  I was 21 years old and had just finished college, and was delighted to be earning. It might not have been the most glamorous job, but it laid the foundation for a spirit of determination and resilience. 

What pushed you to pursue a career in this field? 

I always wanted to be my own boss. With my degree in Business Information Systems from UCC, I was always drawn to the world of technology, which was rapidly evolving, with its endless possibilities and innovations, hence my course of study. The idea for WeddingDates came about while working in recruitment. I noticed many of my colleagues researching and planning their wedding during lunchtime on the internet…I identified a gap and armed myself with a laptop and a copy of the Yellow Pages, and hence, the WeddingDates directory was born!

What would you regard as your greatest achievement to date? 

 Appearing on the Dragon’s Den in 2010 was definitely a nerve-wracking but excellent experience. Expanding the business into the UK in 2011 was a massive step up and it remains as our largest market to date. In 2023, our company won “Best Hotel Technology Product (under 100 employees)” at the prestigious Boutique Hotelier Awards in London.  Honestly though, I’m most proud of the fact that we’re still in business and that we kept pace with all the ups and downs such as the pandemic. 

Beyond these business achievements, my greatest achievements are my twin boys, raising them and buying my beautiful home for us as a single mum.

Career-wise, would you do anything differently? 

I don’t think I would. There is learning to be had from the mistakes that you make and the perspective you gain can be a valuable lesson in resilience and growth. I’m always looking ahead. Rather than dwelling on past missteps, I consider setbacks as stepping stones towards future achievements.

In one sentence, how would you define success? 

To me, success is financial freedom. It’s been the core motivation behind my career journey and why I broke free from the constraints of traditional employment so early on.

What’s the best piece of advice you’ve ever been given? 

The best piece of advice I ever received was to surround oneself with great people. This nugget of wisdom has stood out to me over the years, both personally and professionally. It’s important to build a strong support network, and I’ve worked hard to do that. I have no doubt that this has hugely contributed to the sustained success and longevity of the business.

How do you motivate yourself and your staff? 

I take great inspiration from the incredible people around me. A seemingly innocuous conversation with someone can lead to great curiosity and innovation. However, when it comes to moving forward with something, I will seek advice, but I try to trust my gut. If it doesn’t sit well with me, I won’t proceed.

How do you handle adversity? 

As mentioned, I tend to look forward, so in the face of adversity, I make time to acknowledge and reflect. What are the current outcomes? Do we need to address those outcomes? What led us to this point? What, if anything, could we have done differently? We make time within the business to debrief after all major events and projects, so that the learnings are documented and shared with the team, ensuring we do better next time. 

How do you relax? 

I relax by spending time with the most important thing in life, family and friends. I love to do Yoga, it keeps me grounded, and I love to read. I really enjoy the outdoors, doing any activity such as walking, hiking or swimming. In recent years I’ve discovered the joy of running!

What are your aspirations for the future of the business? 

Over the past 16 years, WeddingDates has evolved greatly. The directory is still very much a successful product in our portfolio, however, our wedding venue software WedPro by WeddingDates is our primary focus in the coming years. It is a powerful solution that helps venues manage their wedding enquiries from all sources over the complete wedding journey.  This year, we plan to expand into new international markets outside of Ireland and the UK. 


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