Welcome to this first episode of our Legal.io Community Spotlight, a series in which we highlight the careers and experiences of some of the most impressive legal and legal operations professionals working in-house.

In this episode, we dive into the career journey of Jessica Vander Ploeg, VP Legal Operations at Micro Focus. Jessica started in the operations field, and has continued on this trajectory throughout her career, gaining experience in the legal operations field at companies such as Elevate Services and NetApp. Pieter and Jessica cover:

• Jessica's career journey to date
• Key responsibilities in her role as VP, Legal Operations
• Key challenges and lessons learned along the way
• Change management and the benefits of “micro dosing” the legal department

Three takeaways from this episode include:

• Career success comes from taking opportunities and stepping out of your comfort zone. It's ok to take that big leap. 
• Early experience as a Chief of Staff provides valuable insights into operational and executive behavior, and provides a strong basis for entering into a legal ops role.
• A successful legal operations professional requires strategic planning skills, passion for technology, a willingness to fail fast, and training and mentoring abilities.

Read the full transcript for this episode below. Are you a legal operations professional or considering entering the field? Join Legal.io to discover legal operations jobs, resources and more. Do you work in-house and are you interested in sharing your career journey and experiences with the community? Apply here to be featured in a Community Spotlight. 

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Pieter Gunst

Today, I'm very excited to have the opportunity to speak with Jessica Vander Ploeg, senior director of legal operations at Micro Focus, an international software and IP company.

Jessica, thank you so much for joining us today. Right before the holidays.

Jessica Vander Ploeg

I am absolutely thrilled to be here and thank you for the invitation.

Pieter Gunst

Excited to chat. Jessica, let's dive right in! Could you tell us a bit more about your career journey and how you got to where you are today?

Jessica Vander Ploeg

I would be thrilled to. So, I started in operations and I've been in operations my entire career. I joined legal operations about four years ago, and it's been an interesting ride. It's been non-linear, there have been steps back, and there have been steps forward. But honestly, my entire career has been built on saying ‘yes’, recognizing a good opportunity when it presents itself, and being willing to do something when maybe I'm a little bit afraid.

I don't think any good opportunity comes out of comfort. So if you're willing to step out of that comfort zone, which I think I've been willing to do, great opportunities present itself. I actually started in market research after a few years, said ‘yes’ to a great opportunity in court reporting. A number of years later said, ‘Yeah, I'll try that alternative legal service provider’. And just months after joining an alternative legal service provider was invited to come in-house with NetApp. And that's really where my legal operations career began. I was able to train alongside some of the best and, you know, someone that I would call the Mother of Legal Operations. That was an incredible journey. A few years after being with NetApp, I had this crossroads moment where I could stay in that comfort zone and continue to grow, or I could take that next big scary role. Take that next leap in my career.

So after meeting the Chief Legal Officer for Micro Focus, I decided the next big scary leap was the role for me. I've been with Micro Focus for the last seven or eight months now working on transformation and a number of fun projects there.

Pieter Gunst

Amazing. And I was really intrigued to see the variety of roles you've taken leading up to this point in your career. I saw, in particular, that you joined as a Chief of Staff pretty early on in your career as well. Has that experience been informative? And driving in your later roles?

Jessica Vander Ploeg

It absolutely has. I was very fortunate to be able to sit alongside a CEO early on in my career and learn the differences and the nuances that happen around a boardroom table or in an executive meeting. Being able to learn that so early on; pick up that nuanced behavior and that attention to detail for when you speak, how you step in, and what that executive presence should look like, has benefited me so much throughout my career.

Pieter Gunst

And I can imagine that seeing the operational side of the business at the highest levels so early on really drives a lot of insights and then effectively helping your stakeholders in a legal operations role.

Jessica Vander Ploeg

Absolutely. I think it helps me to better understand the individuals that I'm working with and just better appreciate their position. So legal operations - we're change agents. So how do we come to the room, appreciate what other people are doing and at the same time help to drive uncomfortable change? It's a very delicate balance.

Pieter Gunst

I hear that from a lot of legal operations professionals in the space. Now, taking us to your current role at Micro Focus. You're a Senior Director of Legal Operations there. Can you tell us a bit more about your day-to-day responsibilities in that role?

Jessica Vander Ploeg

Sure. Absolutely. A lot of it is the strategic planning, acting as the right hand to the Chief Legal Officer and just trying to understand where we are now, where we want to go in the next 6-12 months, and where we want to go long term. So a lot of it is the planning, the operational aspects of the strategy, and figuring out where we are and where we head.

Alongside that, there's also a lot of technology oversight. As you can imagine, with legal operations, where we're heading (from a tech perspective) is a big part of what we do and what we want to think about. So what technologies are we onboarding? How are we managing them? Do we need new technologies? What problems are we going to solve with those technologies? That's a big piece of it. And being the the Global Head of Operations for Micro Focus, a big part of what I do day in and day out is training and mentoring. And that's one of the aspects that I find most rewarding. Whether it be bringing someone in from a consulting firm who is so wildly talented and giving him his first in-house role and helping him to learn the legal side of things. There's a lot of intrinsic value in that for me, but it's also a big part of the role in general. So how are we bringing up the next generation of legal operations professionals? And what is that going to look like? And how do we ensure that they're well-connected and well-prepared? And I think too, in this role, at this level, there's so much collaboration that happens and just oversight in general. So, sometimes I'm ‘in the weeds’, sometimes I'm doing the tasks, and other times it's ensuring that the team can do it and that they have the support and the collaboration. And I'll give you a really quick example: My counterpart, Steven, who is brilliant with technology, has been helping us to onboard a new technology. A piece of that is we want to automate signatures. While he's been managing the tech aspect of it, getting us up to speed and managing IT, I've been going to the signatories and saying, ‘I know you don't know me, but can I have your signature on a .jpeg? I promise I won't do anything bad with it’. But it's that collaboration and that trust that we as legal operations leaders have to build to then move our projects to the next level.

Pieter Gunst

Yeah, I love your focus on team-building. You really strike me as a leader that anyone would be fortunate to be on that team. Now, paint me a bit of a picture in the evolution of your role towards the senior leadership position, right? How does it compare going from the management role at NetApp (or any roles you saw before that) to getting to this highest level within the legal operations department?

Jessica Vander Ploeg

It's so different and I didn't appreciate it as much as I should have. When you're in that head role, there's so much strategy that goes into it. Long term planning, the collaboration, the networking in the industry - really making a name for yourself in your organization. And when you're in that role - just one level lower, that management role I was in previously - a lot of it is the ‘boots on the ground’ work. A lot of it is the day-to-day ‘in the weeds’. How is the project progressing? What tasks do I have with the project? How is the technology functioning? Do we need to do anything different within the technology? Are we setting up the meetings? Are we meeting with the right people?

So, so much of it was the in the ‘in the weeds’, ‘boots on the ground’ type of work to ensure that everything was functioning properly, so my leader had the ability to think strategically, had the time and the space to get out into the industry and to be that right hand to our Chief Legal Officer. That's such a huge part of that leadership role is making sure that you're there to support that person. So, if you're supporting your Head of Legal Operations, being able to give them the space to do those things is important. And that was a lot of what I did when I was at NetApp.

Pieter Gunst

Hmm. Yeah, very interesting to hear that progression from tactical to strategic. And now in this current role, what are some of the key challenges that you have encountered and also very importantly, what did you learn from those along the way?

Jessica Vander Ploeg

I think one of the biggest challenges for any legal operations professional is just change management in general. But I get really excited and very passionate about technology, so I can often ‘jump the gun’ or be really enthusiastic about it. So I'll say, ‘It's the best technology! It's going to change the world! We're going to do things so differently. It's going to be perfect!”, because I get so excited. But we all know as Legal Operations professionals, no technology works perfectly, especially out of the box. Oftentimes it needs training or it needs time, or you have to go back in and tweak things once you've launched. And so I have found that I need to scale my excitement back a bit, add some reality into the conversations that we're having around technology, and really prepare people for what's coming.

So in the last eight months, we've onboarded three new technologies within Micro Focus, which can be a lot for anyone. We're starting on our fourth next month. Our second technology could have been considered a failure. It wasn't received well once it was implemented. The team did not give positive feedback, and they really weren't excited about using it going forward. It was a great opportunity for me to take a step back and say, ‘How could I have done this differently? How could I have prepared my team better? How do we ensure it's a success going forward?’ But I think my biggest takeaway was it was a wonderful opportunity to be able to teach my legal department about failure and to stand up and say, ‘It's okay to fail as long as you're going to fail fast and then fix it’.

I don't think any technology can really be a failure unless you just give up on it. How is it received? How is it being used? Is it being actually implemented and used well? And so now we're making some tweaks and we're starting to see that progress. - It's okay to fail, but fail fast and then tweak so that you have some success afterwards.

Pieter Gunst

Jessica, that's amazing advice. And one of the things that I really enjoyed in our previous conversations as well is how conscious you are of all the moving parts and then the stakeholder alignment it takes at the planning phase and then beyond to really have a project to be successful. And one of the intriguing notions that you used, is this notion of ‘microdosing your legal department’ I believe in the context of change management. Can you talk a bit more about that idea and how you've put that into practice?

Jessica Vander Ploeg

I'm absolutely thrilled to. It's one of my favorite things to talk about right now and to do to my legal department. So when I think about microdosing, I think about allergies (to aspirin or to a peanut), and how much can someone take before that allergic reaction kicks in? So, if we can give them little doses along the way of aspirin or technology or change - take your pick! - then they become less susceptible to that allergic reaction.

I think one of the things I realized early on at Micro Focus, was that people were really excited. ‘Oh my gosh, we're going to change! We're going to transform. There's going to be technology!’ And then as it started, they would say, ‘I thought you were going to do it over there. I didn't want my things to change. I wanted you to make great change, but just at arm's length from me’. So I realized very quickly that change in small doses was going to be how we found success. It was about having conversations early on, implementing just one piece of the technology, and starting with just one group or one geographic region, and then expanding from there. 

Instead of getting this intense allergic reaction from our legal department by saying, ‘Here's a new technology, here's every feature, use it every day, all day long’, we said, ‘Here's one workflow. Here is your one thing to do. Would you be willing to test it for us? Would you give us feedback on this one aspect?’ Being able to actually bring them to the table in doses and in pieces really helped with trust. It helped us with change management. It helped us with adoption. It allowed people to come to the table with an open mind. We weren't going to change everything that they were doing on Day One. We were going to offer them one piece that was going to help take five minutes out of their day. Or Legal Operations was going to do one thing and it was going to save them 15 minutes this week. Just that one change. That at least opened their mind to the idea and allowed them to be willing to think about change, or to think about working differently. It's really helped us to build this incredible relationship with our legal department, where Legal Operations isn’t eating lunch alone anymore, for lack of a better term. Or they're not wanted in the room. We're now wanted there, and we're brought alongside to say, ‘How can you help us?’ and ‘What do you think?’ and ‘What new technologies have you heard of?’. It's really opened the door for a lot of incredible change.

Pieter Gunst

Jessica, these are amazing lessons. Thank you so much for sharing a bit of the background on your journey, your excitement, but also your notes on taking that excitement and converting it into change one step at a time as an effective means of running and scaling a Legal Operations function. Thank you so much for spending some time with us right before the holidays. I really appreciated getting your insights during this short spotlight.

Jessica Vander Ploeg

It was an absolute pleasure to be here. Thank you so much.

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Do you work in-house and are you interested in sharing your career journey and experiences with the community? Apply here to be featured in a Community Spotlight. 

Are you a legal operations professional or considering entering the field? Join Legal.io to discover legal operations jobs, resources and more.