Cian McLoughlin - CEO at Trinity 🇦🇺

This week we feature Dubliner Cian McLoughlin, CEO of Trinity, a startup which has had a huge 2023 having picked up several awards including the 'Outstanding Start-Up' in the Business NSW Awards for 2023 as well as closing some impressive partnerships.

Trinity is a leading provider of Win Loss Analysis software and services, unlocking honest and actionable customer insight from every sales opportunity, win, lose or draw.

In 2022 Trinity launched their automated win/loss review platform, to complement our consulting-led reviews, allowing Trinity users to capture win/loss customer insights straight from their CRM.

Here’s a quick 60-second preview of what to expect, including how Trinity has gone from a clickable prototype to a salesforce CRM ecosystem partner in two years:

Enjoy Cian and Trinity’s incredible story, especially a personable video at the bottom of this post about what it means to Cian to be an Irish founder abroad. ☘️

1. Tell me a bit about yourself and your background. When did you decide to move abroad?

I grew up in Dublin, and I moved to Australia in 1998. I had just finished my postgrad at Smurfit Business School and decided to strap on the backpack and come out to Australia for a year. Fast forward 25 years, and I'm still here. I was lucky enough to meet a girl from South Africa while backpacking, and we found a Sydney was a happy middle ground between Ireland and South Africa.

Like a lot of people when arriving in a new country, I had various jobs in the first 12 months, but I decided to stay. I wanted to get sponsored, and I met a guy in Recruitment, who I knew from playing football, who said he'd get me interviews.

One of those interviews was with a small software company looking for its first inside salesperson. I knew nothing about software or sales, but I needed a job, so I convinced them and got the role. That was my entry into the technology sector, and I've been in the B2B sales industry ever since.

2. Tell me about the business – what it is, what it aims to achieve, who you work with.

After getting a lucky break with my first sales role, I spent the first decade of my career working for B2B tech companies like Cognos and SAP. During my time in these roles, I noticed a gap in our understanding of why we won or lost sales, despite putting so much effort into each pursuit.

This led me to start reaching out to customers for feedback. I eventually quit my corporate job back in 2011 to set up a Consulting business, conducting Win and Loss reviews for tech, telco, and professional services companies globally.

In 2021, I took all of the knowledge and experience from my consulting business and launched a new SaaS solution, focused on Win-Loss and value realization reviews. We recently announced our partnership with Salesforce to integrate our offering globally through the Salesforce app exchange.

3. How are you funded?

Funding-wise, for the first 12 months Trinity was fully bootstrapped, allowing us to retain full control of our vision for the business and product roadmap. About 12 months ago, we invited a small group of angel investors to join us and, as we plan our growth for 2024 and beyond, we’re exploring different funding options to support our expansion into the US, AI strategy and other key growth milestones.

4. What has been your biggest challenge so far and how have you overcome this?

The biggest challenge in the past two years has been adapting to the SaaS model. Unlike traditional businesses, SaaS requires significant upfront investment before seeing incremental returns. Balancing development, expenses, and building a team while being bootstrapped was challenging.

I've got a lot more grey hair two years later than I had at the beginning of this process.

5. Trinity took out the 8th spot on the 2023 Deloitte Tech Fast 50 What’s in store for the future?

We're doing a lot of work around our AI strategy because we don't want to just capture win-loss feedback, we want to interpret it and deliver back clear and actionable insights for the leadership teams we support. AI and LLMs are the key to unlocking interpretation at scale and provide an immense opportunity for this vast growing industry vertical.

We're also focused on expanding our presence in North America in 2024. Initially, we’ll be focused on building our brand recognition and awareness around this topic generally, whilst adding new customers and partners. Although the premise of Win-Loss Analysis is deceptively simple, still only a few businesses have a clear and consistent strategy around Win-Loss.

6. What does it mean to be an Irish founder abroad?

You know it's a great question. I've been here literally half my life (25 years). So even though I 100% still think of myself as Irish, I haven't necessarily thought of myself as an Irish founder…but then when you meet people you realise that's how they think of you.

I think we also have a global view. Coming from Ireland you're always looking outwards to the world. We (Trinity) are looking to the US and Europe very very quickly whereas other companies may take a little bit longer to start tracking into those markets

7. What advice would you give Irish people abroad who might be thinking of starting a business?

My advice for Irish people abroad thinking of starting a business is this:

Choose your path, and don't underestimate yourself. I didn't come from an environment where I knew people had started businesses. You get to choose your path. Don't tell yourself that starting a business is for someone else or that starting a business is beyond you.

I'm also a big believer in starting with a side hustle while having your main job so you can do your research and due diligence.

At the end of the day, what's the worst that can happen? the worst thing that can happen is that you fail, but there are ways you can mitigate the risk of that then even if you do fail at least you've given it a crack. I'd far rather be in that position than spend the rest of my life wondering what could have happened.

8. Last question, What do you miss most about Ireland?

Family, especially with time. With my folks getting older, staying connected becomes crucial. I'm looking forward to going home for Christmas, as it still doesn't feel quite like Christmas in 40-degree weather.

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