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Women In Wellness: “Tie an action today to how it’s going to benefit you tomorrow” With Legacybox COO Jill McKay Wilson

A lot of our day to day is dictated by habits. And we all know that changing a habit is hard! There are days I struggle to motivate myself to go to the gym. For me, it’s been helpful to tie my action today to how it’s going to benefit me tomorrow. So if I […]


A lot of our day to day is dictated by habits. And we all know that changing a habit is hard! There are days I struggle to motivate myself to go to the gym. For me, it’s been helpful to tie my action today to how it’s going to benefit me tomorrow. So if I make it to the gym tonight not only am I going to mentally feel better because I can work through any lingering issues from my day but I’m also going to physically feel better because I’m building strength.


I had the pleasure to interview Jill McKay Wilson. Jill is the Chief Operating Officer at Legacybox,. As Chief Operating Officer, Jill oversees the Marketing, Design, Development, Customer Service and Human Resources departments. Jill thrives on maximizing opportunities, stacking wins and bringing order to chaos by creating scalable systems. As a proven leader of high achieving teams, Jill is energized by helping others learn, grow and succeed.


Thank you so much for doing this with us! Our readers would love to “get to know you” a bit better. Can you share with us the story about how you first got involved with Legacybox?

Absolutely! I was introduced to Nick Macco and Adam Boeselager, the founders of Legacybox, about six years ago by a mutual friend. We grabbed coffee and talked through Legacybox’s needs and my experience to-date. At that time they weren’t hiring, but a few months after, I found a note in my inbox asking if I was available to meet. Their team was ready to start dedicating efforts towards building up their marketing team and thought I’d be the perfect person to lead the charge! I’ve never looked back. Since joining the Legacybox team in 2015, the company was named one of “America’s Fastest Growing Companies” by Inc. Magazine with 1,075% growth, but what’s been most exciting for me is the security and peace of mind we’re offering our customers as we help convert priceless aging tapes, film and pictures into digital keepsakes that are ready to pass on for generations to come.

Can you share the most interesting story that happened to you since you started your career?

I learned early in my career to maximize every opportunity. My first gig out of college was working as a designer at an advertising agency. As part of their onboarding, new designers competed with senior designers on client projects so we’d both take a stab at the project, leaving it up to the client to decide which concept they loved most. One of my first projects was branding for a non-profit’s annual fundraiser. I was eager to prove myself, so I worked long hours and made sure I was really proud of my concept for the invitation. On the day of the client presentation, I dressed professionally, had all my materials ready to go, and had practiced my pitch over and over. My senior colleague showed up in a sweatshirt and jeans and stumbled through her presentation. To her this was just another day. I remember her commenting, “Did I miss the memo? Were we supposed to dress up?” I beamed from ear to ear when the client declared my invitation concept their favorite. Because I chose to maximize that opportunity, my work received a ton of exposure — it was featured on numerous billboards, in print ads and in digital placements. Plus, I got to help raise money for a great cause.

In your opinion, what is your unique contribution to the world of wellness?

Legacybox literally gives people back the best times of their lives. We digitally preserve family’s recorded moments trapped on videotapes, film reels and photos so they can be shared for generations to come. I love hearing how Legacybox has enriched our customer’s lives after allowing them to relive their most cherished memories with their families. There’s a sense of security and peace of mind that we offer our customers centered around some of their most cherished possessions. Plus, revisiting old pictures or home movies triggers buried memories and emotions faster than any other method, so gone doesn’t have to mean forgotten.

Also, we help you digitally declutter your life. We take all those home movies, photos, film reels and audio cassettes that are collecting dust in your attic and convert them to digital. You get them back on a watchable disc set, convenient thumb drive or digital download. Imagine getting rid of all those bins of antiquated media AND being able to access and enjoy those recorded moments from anywhere!

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

There are several people I am grateful for, from my amazing husband who has always supported me and challenged me to try new things; to a high school teacher who helped me find my passion for art and visual problem solving; to inspiring mentors, colleagues and friends. One person that stands out is my dad. He taught me to find what I loved and invest in it to make it my profession. I’m a believer that work shouldn’t feel like work. One pillar of this lesson is self-awareness about what makes you feel fulfilled and whole. This advice led to a few pivots in my career as I learned what I liked about certain roles and what I was missing in others. One example is when I was working as a designer and I realized that I missed analytics and strategy, so I decided to go back to school for my MBA. That has opened so many doors for me and has enabled me to have a fulfilling career today.

In your experience, what are your lifestyle tweaks that can dramatically improve one’s wellness?

A lot of our day to day is dictated by habits. And we all know that changing a habit is hard! There are days I struggle to motivate myself to go to the gym. For me, it’s been helpful to tie my action today to how it’s going to benefit me tomorrow. So if I make it to the gym tonight not only am I going to mentally feel better because I can work through any lingering issues from my day but I’m also going to physically feel better because I’m building strength.

Can you share a story of how your company has truly impacted someone’s life?

There are so many, it’s hard to pick, but one recent story that stands out is from a customer whose dad had six siblings. Unfortunately, her dad’s youngest sister passed away tragically when she was a child. The family decided to have a 50th birthday celebration in honor of their late sister. One of the nieces was curious about her late aunt and unbeknownst to the family had some of their old Super 8 family films digitized. The film contained family vacations, Christmas mornings and several other milestones from the late sister’s childhood. She compiled these into a highlight reel and played it at the 50th birthday celebration. All of nieces and nephews who’s never met their aunt were able to see her on screen and it was an especially moving moment for the parents and siblings who were able to revisit and celebrate her life on this very special day.

Is there a particular book that made a significant impact on you? Can you share a story?

This is such a hard question! I’m a big reader and usually have a couple books going at a time. Quiet: The Power of Introverts in a World That Can’t Stop Talking by Susan Cain probably had the biggest impact on me. Cain helped me understand not only myself but also those around me. For example, my husband, is an introvert and needs quiet time to recharge after a day’s work. Whereas when I get home I immediately launch into questions and want to debrief on everything that’s happened since I saw him that morning. This book helped me understand our differences and how we approach different situations. He seems to appreciate it when I give him a few minutes to decompress after his day before peppering him with questions. Other favorites are The Boys in the Boat by Daniel James Brown, Who: The A Method for Hiring by Geoff Smart and Randy Street, What I know for Sure by Oprah Winfrey, Grit: The Power of Passion and Perseverance by Angela Duckworth, and The Art of Happiness by the Dalai Lama.

If you could start a movement that would bring the most amount of good to the most amount of people, what would that be?

I’m a big believer in the power of positivity and positive thoughts. If I could start a movement, I’d empower everyone to control their thoughts and think positively as a means to attract happiness, health and abundance.

Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?

The boy scouts have a rule, “Always leave things better than you found them.” My dad is an Eagle Scout so this has been ingrained in me since I was a child. I always want to leave things better than I found them. This could mean picking up a piece of trash on the sidewalk, improving Legacybox’s onboarding process so all new hires have a great experience, truly listening to our customer base to tweak our digitizing process, or helping my friend turn their rough day around with a funny story.

Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why?

I’m a big Oprah fan. I love what she stands for and the messages she shares with the world. She also embodies the Boy Scouts motto of leaving things better than you found them. I’d love to sit down with her and hear first-hand about her experiences and how she got to where she is today.

What is the best way our readers can follow you on social media?

I’m on LinkedIn and Instagram @jill_e_mckay.

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