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6 Questions for Brightflag’s First GC, Laura Gleeson

Laura Gleeson joined Brightflag as Director of Legal and Compliance in July 2021, bringing a well-rounded perspective from more than a decade of experience in senior in-house and private practice roles.

In her third year of advancing the department and expanding the team, Laura takes on the broader role of General Counsel and Vice President of Legal and Compliance.

We sat down with Laura on the eve of this promotion to discuss milestones along the path to her new position and the mindset she’ll carry into it.

You launched your career within Ireland’s largest law firm before gaining in-house experience at an engineering company with a half-century of heritage. Has working in an earlier-stage, high-growth business like Brightflag impacted your approach to risk management?

My original move in-house after my time in private practice was the more challenging transition to navigate in terms of adapting my approach to risk management.

As a transactional lawyer in a large corporate law firm, I was used to dealing with high-risk, high-value transactions where my clients instructed me as a subject matter expert. While I needed to move quickly to deliver strategic advice and quantify risks—often in real-time—I benefited from the vast infrastructure that comes with working in a large corporate law firm.

Contrast that with in-house, where you are often working on a lean legal team (or where you may be the entire legal team!) and, on any given day, can be asked to advise on various complex (sometimes novel) legal issues and risks.

I quickly felt a newfound tension between wanting to consider and formulate a detailed response and assessment to each novel issue that came my way and the importance of working with the business to move quickly to quantify and balance risk to seize opportunities as a growing business needs to do. This dynamic is amplified in a startup environment, but the same principles have always helped me stay focused.

What strategies helped you transition from private practice lawyer to in-house counsel at Brightflag?

For me, it started with building relationships and trust across every team in the business and learning their strategic imperatives. I knew I couldn’t assess risks effectively unless I understood the business context. So whether our team is considering a product update or exploring a corporate transaction, I strive to make myself part of the conversation as early as possible.

Next, whatever the legal issue presents itself, I always bring it back to basics and apply first principles. Experience and intuition can be applied to any scenario regardless of the technical legal dimension.

The most critical part, though, is maintaining an open mind.

My colleagues have seen that I’ll work alongside them to find creative solutions whenever possible. They know I don’t just say “no” as a matter of course. And as a result, I can trust them to keep me apace of their plans and accept that if for any reason I do need to say “stop” or “pause,” they trust that I have good reason for doing so.

How has your perspective on legal tech evolved throughout your career?

In a word? Massively.

Part of the shift came purely from the passage of time. During my time in practice, I don’t remember legal tech being talked about in any material way until maybe 2010. And at the time, the dominant narrative was that the tools took forever to implement, were prohibitively expensive, didn’t deliver much value, and were generally more hassle than they were worth.

Product quality and choice have improved exponentially since then, giving just about every lawyer – whether operating in practice or industry – a reason to reevaluate. But leaving behind the operational infrastructure of a large law firm accelerated urgency in getting to grips with and optimizing available legal tech solutions awareness.

I now lead a lean in-house team that asks each member to wear multiple hats. So I’ve gained a much deeper appreciation of the value tech can provide as a busy corporate legal and compliance team in helping us close gaps and punch above our weight.

As for Brightflag’s technology, in addition to the value the platform brings to our in-house team as we use it daily, it’s afforded me unparalleled insight into how corporate legal departments manage their matters and spend. But interestingly enough, it’s also made me reflect on my time in private practice.

The conventional view was that eBilling software, such as Brightflag, is somehow the enemy of outside counsel. But now all I can think about is how many contentious conversations would have been avoided during my time in practice if every client had used a system like Brightflag that supports both parties to manage financial expectations, set realistic budgets, allows for real-time reporting and approval of fees and encourages open and transparent communication in relation to legal fees.

What will and won’t change about your responsibilities as you step into this new role?

I’ll still be leading the day-to-day activities of Brightflag’s legal and compliance function. So that means continuing my work advising senior leadership on emerging legal issues, trends, risks, and corporate governance, supporting the business with customer contract negotiations or new product features, and acting as our in-house expert on privacy, intellectual property, and employment law.

The true change comes with the Vice President title and the resulting role on Brightflag’s senior leadership team. It means I’ll have frequent and direct involvement in strategic initiatives that impact the business more generally and will have a role in shaping the business’s future direction, which I’m really excited about.

And I just have to say, the fact that I can assume those additional responsibilities is a real testament to my team. In addition to being great people and colleagues that I enjoy working alongside, it’s clear that they’re also highly regarded across the company and ready for advancement in their roles.

What are some of the challenges you expect to face?

It may be a familiar challenge, but I know it will be as difficult as ever to keep pace with everything changing in the legal world and the tech space within which Brightflag operates.

Even just within the arena of artificial intelligence, there are so many opportunities, but with those opportunities come risks that squarely impact Brightflag, which are changing daily. And with innovation and regulation evolving so rapidly and varying widely across regions, it’s enough to fill a full-time job trying to stay ahead of the many changes coming our way.

The other primary challenges relate to Brightflag scaling as a business. With the pace of growth and sophistication of the business always increasing, the team and I will frequently have to reexamine how we work. Are there more efficient tools we should be employing? More effective ways of working or communication we should be embracing? Are there new and better ways to support the business as it scales?

I find all the uncertainty more exciting than daunting because I know huge opportunities are waiting to be discovered along the way. There’s certainly no prospect of being bored any time soon!

Do you have any advice for women in the legal field hoping to find their path to a GC role?

My key advice is to back yourself.

Women are particularly susceptible to imposter syndrome and often don’t put themselves forward for advancement for this reason. And we know that law is a highly demanding profession that will inevitably ask a lot from us and deliver many setbacks along the way. So you need a go-to plan that protects you from your inner critic whenever it presents itself.

First, try to remember that perfection is neither possible nor expected. I’m a big believer in the value that comes with failure and making mistakes. I’ve always learned more from things that didn’t go well or to plan than those that did. Mistakes are how people learn and evolve in any career — lawyers included.

Next, lean into your network and think about colleagues you can turn to for advice or support. Whether a formal mentor, a supportive peer, or a friend in the industry, having advocates and champions in my corner has made all the difference over the years. So don’t be afraid to ask for help and invest in your network before you need it.

Finally, for those struggling with self-doubt or feeling that they are holding back from moving to the next phase, I’d recommend the simple exercise of thinking about the advice they’d offer to a colleague or friend facing the same situation. The compassionate advice and encouragement we tend to give others is often precisely what we need to hear ourselves.

About Laura Gleeson

Laura first joined Brightflag in July 2021 as their Director of Legal and Compliance. Prior to joining Brightflag, Laura held the role of Senior Legal Counsel with PM Group, and spent over 10 years working at Matheson, where she worked her way from Trainee Solicitor to Associate to the role of Partner to the Finance Group. Laura holds both a Masters of Law by Research, LL.M and a Law and European Studies, LLB from the University of Limerick.


Brightflag is a comprehensive cloud software solution for managing global legal spend, including the ability to: centralize vendors and rates; set and track budgets; manage matters; review and approve invoices; collect accruals; and run reports on everything.