I was immensely proud last week as we announced that Workvivo had raised a $16.2 million (€15m) Series A investment round, led by Tiger Global in New York, with participation from Frontline Ventures and Enterprise Ireland. This week we also marked 3 years since John and I made the decision to build something together, and I thought both of these events were pretty good excuses to give a little insight into our story to date.

Where It All Began

Before going into how Workvivo itself was started, I’d like to start off by giving some context on how John and I first met. Back in September 2007, both John and myself were about to enter a new chapter of our respective careers by joining CoreHR, an enterprise payroll and HR software company based in Ballincollig, Co. Cork. I was joining as a newly graduated software engineer, while John was bringing his experience heading up global support for EMC to lead the charge as the company’s Chief Operating Officer.

Despite joining at very different ends of the corporate ladder, John and I hit it off early. One of the first things John looked to improve in CoreHR was the customer experience, and I got involved in a project to help deliver a robust ticketing and incident management system that John was championing. Our mutual respect and rapport only grew stronger over the seven or so years we worked together.

An early photo of myself and my Workvivo co-founder John Goulding, taken at the launch of my book Beginning CouchDB, in March 2010. Forgive the horrific quality!

My overarching memory of John’s impact in CoreHR was his incredible ability to take a seemingly dire situation and turn it into a positive outcome. I remember circumstances where customers were on the brink of cancelling contracts - and by the time John was done, those same customers were our biggest advocates, doing reference calls and helping us win new business. When it comes to customers, there is nobody on this planet as good as John. It’s hard to explain with words, but he can diffuse tension, make people smile and assuage any fears or trepidations a customer might have - all in the space of a thirty minute meeting.

From the frying pan into the fire

In early 2014, there were two significant moments in my life. My wife Jill gave birth to our beautiful first child, Lily - and I handed in my notice at CoreHR. After seven years giving my heart and soul to the company, it had become clear that for me to achieve my ambitions, I would have to move on. I had always wanted to start my own company - and I felt I needed to experience what it was like to work in a startup before I was ready to try and build my own.

I first met Gareth Cuddy in 2009, when he tried to convince me to leave CoreHR and help him conquer the world of digital publishing. I still remember him pulling up to my house in a convertible Alfa Romeo, before selling me his vision for the world of eBooks. At the time I believed I couldn’t make the leap to a risky venture because I had a good job, I saw a great future for me at CoreHR and I had a mortgage to pay. The truth is that I just wasn’t ready. Over the years I’ve passed up on opportunities to join some really great entrepreneurs on their journey - but Gareth persisted, kept in touch and in early 2014 I was ready.

I spent the best part of 18 months working with Gareth. We renamed the company to Vearsa, launched multiple new products, won contracts with some of the biggest publishers in the world and had some epic times both in Cork and New York, where Gareth was based. When Gareth hired me, he knew it wasn’t the endgame for me - I was always going to move on and forge my own path - so I don’t think he was too surprised when I took him for breakfast in Crosshaven one fine morning to break the news that I was leaving.

The career mid-life crisis

I was in a band once. I was about thirteen, and we called ourselves Full Eclipse. We practiced a few times in my parents’ garage, wrote one song and in true artist form, we disbanded soon after due to creative differences. I have always loved music - but I’ve equally always sucked at creating it, regardless of how much I would like for the opposite to be true. So in the complete absence of any musical talent, one morning in 2015 I did what made total sense to my brain at the time - I decided I was going to save the music business with the only instrument I knew how to play - code.

My original vision for Subwoofr was to build an open source music platform that would enable artists to sell digital subscriptions directly to their fans. At the time, the music business had been completely decimated by piracy, and the industry had a general dislike for streaming services, primarily due to just how little artists were being paid by platforms - unless they had many, many millions of plays. Subwoofr would let artists create a new revenue stream by providing deep access to their biggest fans, in exchange for a recurring subscription.

Subwoofr got off to a great start. We signed up some great artists - the likes of Mick Flannery, John Spillane and the Rusangano Family - all of whom were doing really well in Ireland at the time. We raised a small €150,000 investment round. We started to gain some interest in the UK from indie labels, as well as other companies in the industry. Potential partnerships were in the works - things were looking good.

I learned the hard way just how quickly things could fall apart. My co-founder left unexpectedly, seed investment was not forthcoming, and the product went in a completely different path to the original concept as we struggled to stay alive. It was a crazy 18 months, a huge learning experience, but not necessarily something I wanted to ever do again. To this day my wife, Jill - still blames any grey hairs she finds on Subwoofr.

Life After Death

At this point, Jill and I had gone from both being well paid, with good benefits, two salaries and no kids - to no income, no benefits and 2 young children - all in the space of 18 months. I spent a number of months working on consulting projects that helped temporarily repair the complete decimation of our savings that had ensued. As this work started to come to a close in early 2017, I was edging closer to needing to make a decision about what to do next.

Meanwhile, John had gone on to become CEO at CoreHR, and ultimately guided the company to acquisition in late 2015. In early 2017, I heard that John was leaving Core and ventured in to salute him at his leaving party. We had a good chat and vowed to catch up for a coffee soon after. A few weeks later, we did just that.

That fateful coffee was had in 12 Tables in Douglas. As we talked about our respective journeys over the past couple of years, there was an unmistakably energy that drove the conversation towards the future. We strolled around the corner to just outside Exham House and vowed to meet again soon to catch up. Before long, Exham House would become the HQ for our new company.

As excited as I was, I don’t think I actually believed anything would happen. I still felt a huge weight of guilt and stress from the challenges I had put our young family through with Subwoofr. Not to mention that John had plenty of choices about what he could do next - multiple companies wanted him as their CEO, the world was really at his feet. I went home and told Jill about our conversation and essentially she said that she would support me every step of the way if I did decide to try again. I personally could never have made a decision to keep putting our family through such uncertainty, it was her unwavering support that allowed me to do so - something I will forever be thankful for.

Here we go again

At this point, the only decision we had made was that we would start a business together. There was no product. No team. We didn’t even have an idea at this point. In spite of this, both of us were confident from day one. Between the two of us, we had everything we needed to build a great software company. We started off by defining some guiding principles for what we wanted to achieve. Both of us - for very different reasons - had no desire to report to a board of directors or investors, we wanted to build a great, profitable company that would be fun, rewarding and allow us both to provide a good life for our families. That was it, nothing more than that.

As we started off, we had some ideas for what we could build. When we founded the company, we named it “Ladder Technologies Limited” and registered the domain ladder.hr. Soon after, we built a prototype for a freelance recruitment platform called zecruit.com. We even signed up pilot customers, and had a fully functional prototype - including a video where my wife Jill pretended to be a job candidate applying for a role on the platform, which would be pushed to a hiring company over a push notification in our native iOS app!

Neither John or I were ever completely comfortable with this idea, however. Recruitment is one of those segments that everybody tries to revolutionise - but usually naively and resulting in failure. Our idea also hinged on relying on third parties to provide a good service around our product - and we never liked the notion that a customer could have a bad experience with our product due to circumstances outside our control.

Workvivo is born

As we iterated on ideas, time and time again we found ourselves being drawn to the challenge of employee engagement. We’d both seen the world move on from traditional employer-driven performance reviews, and just how negative a force disengagement was for workplaces. The landscape for software in the space was also unestablished - while there were solutions out there, there was no clear market leader paving the way.

One of the companies who bought into our vision for zecruit.com was Morgan McKinley, the global recruitment agency. We went back to them to try to convince them that they should let us help them with engagement, and not only did they sign up - they enlisted an incredible project team of senior executives to provide us with a tight feedback loop and help us iterate on the earliest versions of the product.

Soon after, we signed up Staffordshire University, and they too assembled a project team of senior execs - including their Chief Operating Officer - to help us hone the very first release of our product. This support was nothing short of incredible, and provided us with invaluable insights into what our product needed to achieve in order to be successful - in two very different organisations.

Following this, Trigon Hotel Group and Voxpro also came on board to pilot the product before we brought it to the market, each bringing another unique perspective to how the product worked in different types of companies.

Boxing above our weight

We had a running joke in the early days where we wondered how far we could get without:

1. Hiring
2. Having a website

In April 2018, we welcomed our first hires - Clara Walsh and Ciaran Holland, soon followed by our first engineering hire Ian McCarthy. We last until July 2018 without a website, when we formally launched the product to the market. A month later, a prospective customer requested a demo using the Intercom chat feature on this new website. They were looking for a solution for their 35,000 strong global organisation.

As a 5 person company, we originally felt like it would be a good learning experience for us to see how far we could go in the process. Over time, we would end up being shortlisted. We then made the last seven. The last five. The final three. What went from a shot in the dark started to feel like it was really achievable. In early 2019 we achieved the seemingly impossible, we beat Goliaths like Facebook to win the contract. Since then, boxing above our weight has become par for the course at Workvivo.

As this all unfolded, we continued to grow. We continuously added new customers - great companies of all shapes and sizes. From innovative companies like Immedis and Arlo to organisations with users in some of the most remote parts of the world like Kentech Group. Our team expanded. We started to inch closer to profitability. The aforementioned major customer went live and the project was an overwhelming success.

The A Team

Up until this point, we had deliberately avoided investment. We had opted to go the bootstrapped path and retain ownership of the business. Both John and I are massively ambitious, however, and while we had been enjoying the freedom of doing everything our own way and not having to navigate the investment landscape - we knew that the company was ready to step up a gear. When news of our seed round last year broke, it drew a lot of interest locally and in the US. I knew Frontline very well from various encounters over my years in startups, and as soon as we started talking to them about a potential investment, we knew we wanted to work with them. Will Prendergast and Finn Murphy were incredibly helpful as we started to consider what we needed to scale the business effectively.

With Frontline on board, we met with many investors in the US about becoming the lead investor in the round. In Tiger Global, we found the perfect match for Workvivo. They have the scale and ambition to help us achieve our major potential, and it didn’t take long for terms to be agreed.

Enterprise Ireland have been a fantastic partner for us throughout our journey to date, and we were delighted they chose to participate in the round and continue to support us as we move into the scaling phase.

Looking to the future

Not long after we signed, the new Covid 19 reality struck like a bolt of lightning. Like most companies, we needed to figure out how to operate in this new world order - and it was definitely not the right time to announce a significant funding round. We have been fortunate in that our product is proving to be really helpful to organisations in this crisis, and this has led to an increase in interest and demand. It has also sped up the urgency for solutions like ours, resulting in quicker launches and higher adoption.

We were truly delighted to finally announce the round last week. For me personally, it finally felt real, and afforded me an opportunity to step back for a moment, catch my breath and soak in a sense of achievement. Seeing the story break on TechCrunch reminded me of my days at CoreHR, where every day I would read about the start-ups that were raising series A rounds and dream about one day that being my company. It made me so proud to have finally reached that point.

As we look to the future, we continue to box above our weight. Our credibility and momentum is growing and growing with each passing week. So many companies wax lyrical about how good their customer experience is - in our case, our customers are the ones waxing lyrical on our behalf. We’ve built an incredible team, and as we grow our team both here in Ireland and in the US, we’re forging a path where companies will soon consider Workvivo as an essential part of the communications landscape, alongside the likes of Slack and Zoom.

To say it’s exciting times ahead is an understatement. I just can’t wait to see where the road takes us next.