Ashley Carlisle is the CMO of HyperDraft, a legal automation platform and trusted technology partner to game-changing law firms and legal departments.

A corporate attorney who has worked at large international law firms, including Kirkland & Ellis and Goodwin Procter, she is passionate about pushing the legal industry forward with modern technology.

I met Ashley on LinkedIn (of course!), and we also had a great conversation on Fishbowl as a part of HyperDraft’s ongoing show on the platform. Learn more about her in this Women Who Wow Profile and follow her on LinkedIn to stay up to date with how technology is impacting the legal industry.

Why did you choose your profession?

I have wanted to be a lawyer since I was in the fifth grade. I worked towards that goal ever since and have truly loved the journey.

As for being a marketer, it chose me. When I met Tony Thai, the CEO and Chief Engineer of Hyperdraft, and saw what he had built and how people were using it, I immediately felt a push to help him tell more people. I became obsessed with distributing the message in creative, cost-effective ways that other people weren’t trying.

I often get asked about making the switch or if I like one career path better. Lawyering and marketing are so different that comparing the two is impossible. However, learning about marketing, public relations and business development has made me a better attorney because storytelling is at the core of everything in the law. Litigation writing, oral advocacy, contract drafting, client service and business development all center around a clear and convincing message.

What do you love most about what you do?

I love the law and being a lawyer, even during the periods that it has been challenging. I love helping people solve problems, researching and learning, and working with intelligent, fascinating people.

As for the marketing side of things, I love that marketing is a beautiful blend of creativity and execution. After practicing law at a Big Law firm, I sought a creative outlet and an opportunity to learn new skills. My marketing journey so far has delivered that opportunity and growth ten-fold.

However, I didn’t realize how difficult the execution piece would be when I started. The focus shifting, planning, researching, team coordination, relationship building, constantly changing mediums and time management of it all have been challenging but rewarding.

What’s the best career advice you’ve ever received?

It’s hard to pick one. Three come to mind:

  1. Don’t work hard to work hard. Always think of the bigger picture.
  2. You are the CEO of your career and life.
  3. One of the biggest things people regret is caring about what others think.

Any advice to women about succeeding in the workplace?

Be the talent and publicist. Early in my career, I thought that everyone would see and appreciate my hard work without having to be my own advocate. Eventually, I realized that people are busy, and if I didn’t promote and advocate for myself, I wouldn’t go where I wanted to. Document what you’ve accomplished, update key stakeholders monthly or quarterly, communicate or ask for advice directly, and invest in your future. Don’t wait for things to come your way. Stay proactive and keep moving forward.

Also, rejection isn’t as scary as it seems. Most people won’t remember they said no to you, so you shouldn’t either. Keep pursuing what you want.

What do you wish you could tell your younger self?

Practicing delusional self-confidence is vital for women. Don’t get me wrong; if you are a dreamer, you must be a doer. But so many women, including my younger self, hold themselves back because they fear seeming too confident, are too critical of themselves or fear failure or criticism.

If you want to do something, even if you don’t have the skills or knowledge now, believe that you can do it and start today. If you are willing to be focused and work hard, you’ll be surprised at what you can do.

Men aren’t taught to be scared of being confident. They embrace it from a young age and don’t limit themselves to the extent that many women do. The most freeing part of my career was when I permitted myself to go for what I wanted, even if it felt ridiculous.

I’d also tell my younger self that much of the weird advice, comments and judgments people make about you, even your family and friends are a projection of their issues. Don’t change to make people happy. Treat people right, but be yourself and okay with the fact that you can’t make everyone happy.

How do you achieve work/life balance?

I don’t think work / life balance exists. Some seasons of life are busier than others, and that’s fine as long as you are taking care of your health (physical and mental) and reflecting on your priorities.

For me to feel balanced, I do two things regularly. First, when I plan for the week ahead, I calendar my workouts and at least two instances of quality time (in-person or on the phone) with friends or family weekly. That way, even if I’m crazy busy, I know the bare minimum of what I need to feel good for the week is on my calendar. Second, my husband and I hold monthly, calendared “board meetings” where we go over what’s going on in the next few months, what we need to coordinate, and our priorities and plans for reaching our goals. It’s a great way to stay organized and have some friendly pressure to keep momentum on personal and professional goals.

Lastly, every morning, I focus on gratitude and being present. Running through what I’m grateful for and setting a daily intention to be present in everything I do has made a meaningful difference in my life. Mindset is everything, and I wish I had focused more on this from a younger age.