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“Simplify and Scale” is Andrea Flanagan’s mantra.
After leading the legal function at Tripwire, LeadVenture was a whole new ballgame. Flanagan began as the sole member of the legal team, and before she could make it to “simplify and scale,” she had to build a roster at the software company. It was her first chance to build out a function from scratch, and the GC has delivered.
Value Versus Volume
In Flanagan’s previous roles, in the firm world as well as in-house, she understood the potential pitfalls of driving a team too hard. Flanagan is no stranger to long nights or the voice inside one’s head that demands as close to perfection as possible. She has never been particularly motivated by comparing herself to others because she’s got her hands full trying to measure up to her own expectations.
But that kind of work ethic isn’t inherently conducive to leading others.
“As I began leading legal teams, I found that that kind of mentality can wear people out,” the GC explains. “It doesn’t matter how many rockstars you have on your team. Things are going to break or slip through the cracks, and I’ve learned to focus on prioritizing the value we can provide rather than the sheer volume of work. With that mindset, I can emphasize my team taking care of themselves. There will always be too much work—that’s the nature of working in-house—so you just need to prioritize and be okay with having a list of things you’re not going to be able to get to until tomorrow.”
Automation Opportunities
Flanagan has looked to automation and technology to create more high-level work for her team. She says things always being done one way doesn’t necessarily mean that’s how they should be done going forward, and she’s built a team around her that’s willing to challenge the status quo of workflow and innovation.
Flanagan has worked to retool legal structures within the business that may be overly complicated because LeadVenture has grown several times through acquisitions over the years. There lies both the opportunity for simplifying and scaling.
The legal team implemented a contract lifecycle management (CLM) that served its initial purpose well, but as LeadVenture continues to grow, the legal team is looking for more self-service options.
At the same time, Flanagan says the implementation of a relational database sharing platform has helped automate processes and reporting. Finding the right vendors to work with the legal team’s budget can be challenging, but Flanagan is quick to point out that it’s a common theme among in-house legal departments.
Over the last three years, Flanagan has had the opportunity to get much more exposure to M&A, a process she had never been able to see through to completion previously in her career. Flanagan has navigated about two deals a year since coming to LeadVenture, and this work has allowed Flanagan to continue building out that skillset.
The Value of Balance
When Flanagan talks about wanting her team to be able to focus on their lives as much as their work, she has experienced that change in her own life firsthand. After putting work before just about everything in her day-to-day life, she met and married her husband, Andrew, and gave birth to their daughter, all in just the last few years.
“When we started talking about having a family, this was something I really had to work through because before I met Andrew, I naturally worked ridiculous hours,” Flanagan says. “But suddenly there was this person in the world that I wanted to spend time with and then a daughter [whom] I wanted to be present for. I have this same drive inside me, but I now have to work with a bigger picture in my mind.”
Flanagan says she couldn’t imagine coming back to her job with less drive or motivation, it’s simply a matter of being okay with prioritization and honing her ability to address what needs it most at the right time.
The Flanagan family has worked to simplify and scale in its own unique way. Flanagan and her husband recently bought a small farm in Oregon’s Coastal Range and are slowly developing a homegrown agriculture tech (agtech) company that combines the passions of both Flanagan and her husband. She spent her early summers on her grandparents’ wheat field, pulling weeds and learning to drive in a wheat truck.
“There is going to be a tremendous amount of land turnover in the next decade because of older farmers retiring,” Flanagan explains. “I hope we ca n be a small part of preventing ‘big ag’ from taking over all of those family farms. We want to encourage and support small-family farmers to continue that legacy. It’s a wonderful adventure to take on together.”
