How to Recruit, Run, & Grow a Diverse Global Legal Team | Daniel B. Winslow

After many years spent serving in government roles, what first got you excited about a return to the private sector with Rimini Street?

I really see software as our second Industrial Revolution. It’s where so much creativity and innovation is centered — and I still think we’ve only scratched the surface of what’s possible. So what better way to get in on this massive, historic movement than to join the people who keep software running? Maintaining the revolution requires something a little more sophisticated than wrenches and oil cans this time around, but I see our enabling role as very much the same.

Even more than the space itself, though, I was attracted to the story of the company. Rimini Street (Nasdaq: RMNI) had set out to compete in an arena dominated by some of the largest, best-funded software vendors in the world, and was doing so successfully growing every year. That traction let me know something was clearly resonating with customers. And for me personally, I’ve always enjoyed the challenge of taking on competitors who force me to raise my own game.

Finally, there was also the realization that there is a large total addressable market. So I had a sense that I could soon be growing a small U.S-based legal team into a larger global operation.

The global nature of your team is certainly something that stands out. Are there any habits, systems, or tools that are especially important to you as a result?

I took that initial pressure to scale as an invitation to get away from tradition, away from “the way it’s always been done.” It was a chance to really reinvent the legal function as a business unit that’s open to new ideas, best practices, and innovation. And I guess the first big convention we challenged was geography.

There’s still this belief that lawyers are like farmers, tied to the land. Their licenses are issued according to physical jurisdiction, so their services must be immovable. One thing you notice when working around software engineers, though, is talent can travel if you let it.

By ignoring borders and embracing a flexible office or remote-from-home work model, we exponentially expanded our recruiting network and quickly welcomed some phenomenally talented people onto the team as a result. (We already have local experts in Australia, Brazil, Great Britain, Israel, Korea, and Japan, to name a few.)

The communication tools we use actually aren’t that unique, but I think where we do use tech to our advantage is for minimizing tasks that might distract our focus. We were early adopters of A.I. for invoice review not because it was a shiny new object, but because it literally saved the team dozens of hours each week spent reading, checking, and correcting bills. Now we’re free to focus on more of the things machines can’t do, like strategizing long-term growth plans.

Even if it’s never measured or noticed, though, you inevitably will have to make an extra effort to stay connected as a remote team. That’s why I also want to make sure everyone has a chance to fully disconnect as well.

I have no doubts that my colleagues are dedicated and resourceful professionals who will find a way to get things done when it matters most. What worries me more is people bringing lesser versions of themselves to work because they don’t feel like they have time to develop meaningful relationships outside the office.

That’s what ultimately led to the development of what we call “Real PTO.” We specifically tell any teammate on vacation to avoid email altogether and only check their phones once in the morning and once at night. If we really do need you, then there will be a text or voicemail explaining the request. If not, then enjoy a guilt-free day away.

The diversity of your team definitely goes beyond geography as well. Is there a reason your organization has been more successful in this dimension than most?

The best way to get a job is still by networking in your extended social and professional circles. The trouble is, most people have a network that looks and thinks a lot like them. We’ve tried to counter that bias by taking proactive steps to expand our neighborhood, so to speak.

The Minority Corporate Counsel Association, local minority bar associations, and Military Spouse Employment Partnership, for example, have connected us with exceptional talent we may never have discovered through the usual suspects like LinkedIn. Widening your search is only part of the equation, though. I think the much larger variable most companies aren’t thinking about is credibility.

Candidates ultimately have to choose you as well. If diversity is something you only started thinking about after your first 100 hires, candidates can sense that. If you’re just trying to hire someone that checks a demographic box, candidates can sense that too.

But if you make diversity a priority from the start, like we have, then you’re going to find success begets success. And if you have a record of elevating employees into positions of true authority and influence, you’re going to find that word travels fast in that way too. There’s still plenty of room for improvement, of course, but I think those principles have helped us assemble the diverse team we benefit from today.

Switching from people to process for a moment, it looks like you were also quicker to establish Legal Ops than most companies of your size. What was going on for you around the time you attended the first-ever CLOC conference?

My practice background includes service as partner or senior counsel in several international law firms. And what you learn there is that the biggest firms run more like commercial operations than practice groups. So I quickly came to see the value of business-oriented legal staff.

Even for lawyers, there are only so many hours in the day. Time I spend addressing operational tasks is time I’m not contributing my full value to the business. Now, to be clear, I definitely have visibility into how things are progressing. I’m just not personally crunching every number anymore. So because I have a team of specialists I can trust to expertly manage Legal Ops, my effectiveness as a GC is markedly enhanced.

Do you think that kind of business-oriented mindset within the team makes it easier to collaborate with the rest of the company?

There are two broad categories of lawyers: Those who tell you everything you can’t do and those who tell you how to do it. I like to count myself in the latter camp.

Now that I’m no longer pinned down by Legal Ops items that could be better addressed by specialists, I can be more strategic about aligning legal services to business plans. I have time to look over the horizon and provide the advice and counsel the business needs to steer through complex global risks and take advantage of global opportunities.

So again it’s a matter of focus. You have to keep an eye on costs and you have to live within a budget, but should your GC really be the person reviewing expense line items? I’d rather be the GC that helps the business-side succeed.

The old adage of “we advise but the business decides” still holds true, but I think the best legal departments are seen as partners in the success of the business.

Looking back as the leader of a team that’s now scaled from five to 50, what’s one of the things you’re most thankful to say you solved early?

One of the best things we did early on was develop an org chart we could grow into as a legal team. There were definitely some awkward “teenage years” there in the middle when it didn’t fit us quite yet, but I didn’t want to be constantly changing the vision. Our revenue was growing every year, so having a clear plan of progression we could point to certainly helped reduce the stress.

Everything was horizontal when I started, really just transactions teams. Pretty quickly we branched out into practice specialties and geographic areas of responsibility as well. But eventually I knew we had to get vertical. Compensation is obviously a key lever when it comes to recognizing and rewarding good work, but titles are still very important to our profession.

I wanted to give people clearly marked paths to progress from a junior to senior contributor over the course of eight to 10 years. There’s a level of performance you can only unlock by retaining talent and building cohesion over the long term. And if we treat our team right, they’ll have a chance at delivering excellence to their internal clients every day.

Finally, in contrast to all the good advice you’ve shared so far, is there any bad advice you’ve overheard that you wish would go away?

Maybe on hiring. I think a lot of companies are still too rigid with their experience requirements. There’s definitely a minimum dose required to start, but most relevant experience still comes from the job itself. What’s much less likely to change over time, though, are someone’s attributes. So we focus more on those when assessing candidates.

The trick is making intangible qualities as tangible as possible, so we’re big fans of practical skills tests. When someone tells us they’ve got great instincts on deals we say that’s great — and then we build a mock deal for them to work through.

We’ve been surprised several times by how the years on someone’s resume correlate to their performance in the room. So I’d say stay open to talent that’s outside the conventional norms of the experience profile you think you should be looking for.

That goes back to the point on expanding your neighborhood.

Exactly. And once you get the right people in the door, the formula for success is still pretty simple (if not always easy). Clarify their development path, empower them with tools that accelerate their journey, then treat them as the professionals they are and get out of their way.

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