The last time Dee Coakley and I spoke, we were cloistered away in a media cubby in Lisbon. 

Coakley had just presented on Web Summit’s main stage to 17,000 people, and she moved easily among the throng of Irish founders who annually migrate to Portugal for the event. 

A soigné figure on the Irish tech scene, Coakley stands out in every room filled with branded zippies and organic sneakers. 

As chief executive and co-founder of Boundless, an employment platform that enables employers to compliantly employ and pay remote workers, she also has impeccable timing.

Boundless was founded in 2019, after Coakley went through the head-melting experience of managing employees’ remote working arrangements, while in her role as chief operating officer with Axionista, the media software company. 

It has grown apace since then with the pandemic accelerating attitudes towards a decentralised workforce by roughly a decade, Coakley reckons. 

Boundless is now operating in 22 countries; it currently has a staff headcount of 22 but that is expected to grow to 50 by the end of the year. 

The business uses a Employer of Record model, whereby Boundless becomes the legal employer of the individual employees as far as their government, tax and employment authorities are concerned. Boundless charges 8 per cent of total monthly payroll and is on track to reach 5 million in Annual Recurring Revenue by the end of 2022.

When Coakley and I spoke over the phone last week it was golden hour in Dublin and the ink had just dried on Boundless’s seed extension funding raise of 1.4 million, bringing the start-up’s total funding to 5 million. 

From the beginning Coakley has looked to raise outside of Ireland, and backing her are the UK based Ada Ventures and FyrFly Venture Partners, as well as Enterprise Ireland. 

Dee Coakley: “The issue of diversity in the start-up is not something that has gone away,”

Now, Coakley is about to embark on a new funding raise as the CEO of a female-only founding team, as she gears up for Series A in the summer. 

Boundless started off with three founders, Coakley, Emily Castles and Eamonn Leonard, who departed in September last year, for personal reasons.

“I’ve never raised as part of an all-female founding team before, so I don’t know if it’s going to be different.

“My co-founder is a woman as well, and it is really rare that you’d hear about a VC firm with a portfolio of more than a few women founders, so we are  still so early in terms of diversity.”

While she hasn’t experienced it first hand, Coakley says she knows female founders who have been told, in writing, that if there was a male co-founder involved, they would invest. 

“The issue of diversity in the start-up is not something that has gone away, globally it got worse over the pandemic. A lot of the funding is still going to white men,” she said.

“Being a woman, I always ask if VC firms have female partners, a lot of funds don’t have any, and it is a massive red flag for me if there aren’t. Everyone will claim they have an interest in diversity, but the proof is in the pudding.”

Globally, under 2 per cent of VC funding goes to female led start-ups. Figures compiled by TechIreland, the not-for-profit organisation, puts the figure at 6 per cent in Ireland for 2021.

“VC funds know this is a problem and the ones that are shouting about it are trying to do something,” Coakley said.

As questions over an employee’s right to work from home, or the willingness of companies to be flexible about remote working are being bandied about, Coakley is advantageously positioned to identify trends in the remote working scene in a post pandemic world, and there is one that is a very live threat to Ireland. 

“Portugal is definitely our most popular country,” said Coakley. “The data shows everyone is moving to Lisbon right now.

“A lot of our customers aren’t based in Ireland, and we’re seeing them move there. There’s also Americans moving to Portugal where it’s not as straightforward as people from the EU moving. It is really popular.

“There are a lot of governments that have tried to implement new visa programmes, or worker friendly tax schemes to attract digital nomads during Covid, but most of them don’t really stack up when you look at the small print,” Coakley said. “But Portugal seems to really have gotten it right, especially for founders.

“I would say it is a serious rival to Dublin.”

The cost of living, quality of life and accessibility of accommodation is another reason Coakley has seen people moving to the Portuguese capital. A lot of people also see it as a great place to bring up their kids.

When asked about Ireland as a place to found a business, Coakley grows impassioned. Using the UK, where she lived for a dozen years, as a frame of reference, she says the one area where she thinks Ireland has an advantage is Irish culture and in the ease with which founders can network.

The cost of living and tax

But two glaring issues that are incompatible with founding a business from Coakley’s perspective, are the taxation of employee share options and entrepreneur relief. 

“It is ludicrous to think that you would tax people, who are quite often on low salaries, on share options. The government wants to tax them on a piece of paper that may never be worth anything,” she said.

“In other countries, you’re not taxed until the exit of the company when they share option actually turns into a share.” 

Her second bug bearer is that in Ireland an entrepreneur is entitled tax relief on the first €1 million they make on the sale of their business- rather than the usual 33 per cent capital gains tax it is reduced to 10 per cent.

In the UK this relief extends to the first €10 million made from the disposal of a business.

As employers continue to reckon with a new balance of power which has tilted in favour of in-demand employees, Coakley said there is a greater expectation for added benefits like health insurance and pensions but also integrated wellness programmes from Boundless’s clients.

“We’ve been light on benefits before, but we see a lot of demand in that space. 

“As more and  more companies are having employees go international, combined with the great resignation, and the fact that so many people are moving on from jobs and companies are really struggling to retain people means that there’s big demand for good global benefits products and it’s really hard to do that stuff internationally,” she said.

“Some benefits are in regulated sectors, so things like health insurance, pensions, or any other form of insurance, they’re regulated. So you can’t really buy a global product, you need to go to a provider in each country. That’s very difficult for an employer, particularly if you don’t speak the language or you don’t have any pre-existing connections in a country. 

“But we have all of that infrastructure. So we have a network of accountants and lawyers, in each of the countries where we operate.”

Dee Coakley: “It’s just so fantastic to meet young founders that are at that really excited”

Coakley’s background is varied, after graduating college she lived in London for a dozen years. Initially she worked in different roles across the music industry, before joining the tech world. She has held three chief operating officer positions, first with Masabi, then Bizsimply and finally with Axionista.

Now, as a female founder, with decades of experience across legal, compliance, recruitment sectors, and everything in between Coakley is sharing the advantage of her experience with other founders through a new initiative, First Fridays for Startups. 

 A collaboration between Dogpatch Labs and Irish Tech Hub Networks, First Fridays for Startups is a monthly virtual initiative that will deliver talks, guidance and mentoring around Ireland.

Coakley will be one of several mentors who will give one-on-one mentorship to founders at the very beginning of their ventures. 

“I enjoy mentoring and you’d hear the same from anyone else that says they like doing it. It’s just so fantastic to meet young founders that are at that really exciting stage and have so much enthusiasm for their idea. It’s fun.”