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“Establish A Core Team That Believes They Should Continue To Evolve Both As Individuals And As A Team”

Leadership Lessons With Danielle Gillespie


Leadership Lessons With Danielle Gillespie


Establish a core team that believes they should continue to evolve both as individuals and as a team. That spirit will spread through the company and will create a culture of constant learning, evolving and mutual respect. It is my belief that people thrive in environments where they feel they are wanted, appreciated and that they can make a positive contribution.


I had the pleasure to interview Danielle Gillespie. Danielle is a tech-crazy, wine aficionado with more than 25 years of experience developing commercial software and taking products from inception through deployment. Danielle is founder of CorkGuru, a digital marketing platform for the wine industry and co-founder of thankr app, a video platform for sending fast, fun and personalized thank yous. Her experience ranges across many industries combining technology building blocks to design and deploy cost-effective product solutions for mobile users.

Thank you so much for joining us! What is your “backstory”?

I’m basically a certified tech geek and an enthusiastic wine lover. Life is kind of funny sometimes and as I think back on my career, I must admit that I pretty much stumbled into software development. My first job out of college had a software component and from that moment, I was hooked. I’ve done everything from low level development to high level architecture and really love it when I can see a technology solution making people’s lives better. The wine loving has been a journey I’ve been on for almost as long as my professional career — it really started when I was working for a small company in Boston and they sent me to Europe to teach a class. I was able to travel through the Loire region and had the chance to taste a bunch of really cool wines — not in commercial tasting rooms, but rather farm houses and the barns where they make the wine. One side of the room is a rack of goat cheese and the other is the wine barrels. I thought I was in heaven!

Can you share the funniest or most interesting story that happened to you since you began leading your company?

I started a second company called the thankr app which is an easy way to send a digital thank you. One day I received a thankr from a favorite and early CorkGuru customer AND the thankr developer — they serendipitously met at a tasting room in Napa one afternoon, neither one knew the other but somehow made the connection to me.

What do you think makes your company stand out? Can you share a story?

The hospitality industry is notoriously reactive and constantly bombarded with external requests, keeping the operations running smoothly is a juggling act. Hospitality is also a high-touch industry and the use of the word “guest” versus “customer” is a purposeful expression of their approach to service.

At CorkGuru, we try to mimic that level of service and aim to treat our customers (restaurants) the way that restaurants treat guests:

  • Hands on concierge approach to on-boarding
  • Quick response to questions
  • Retraining new staff
  • Pitch in to help keep menus up to date

I’ve been criticized for giving away some of these services for free but the bottom line is, we just want these menus to be great and we want to eliminate the friction between challenge and solution. We want our customers and prospects to think, “Hey, we’re crazy to not use CorkGuru’s help.”


Are you working on any new or exciting projects now?

I’m really excited about the Alexa device and others like it. Since our main mission is to help restaurants connect with guests not only during the dining experience but also before they arrive and after they leave, these devices will help drive more business to restaurants and help guests with decision-making. Restaurants already have a great asset — their wine inventory — which they can leverage to draw wine-loving guests in. Wine lovers just need to be aware that the restaurant exists and is ready to serve. A spoken language pathway to cut through all the digital clutter will help make informed and timely decisions that will lead to memorable experiences.

What advice would you give to other CEOs or founders to help their employees to thrive?

Establish a core team that believes they should continue to evolve both as individuals and as a team. That spirit will spread through the company and will create a culture of constant learning, evolving and mutual respect. It is my belief that people thrive in environments where they feel they are wanted, appreciated and that they can make a positive contribution.

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?

When I first started on this journey, I realized I needed help with the business side of the project and was introduced to a guy providing “executive as a service” contract services. Even though I could only hire him as a part-time contractor, he believed in what I was doing and consequently leaned in, spent countless hours of his personal time, and has gone way beyond the call of duty. He has been through the ups and downs, has been a mentor, a therapist, and has kept me accountable no matter how ornery I got. I truly wouldn’t have made it without him!

How have you used your success to bring goodness to the world?

I consider getting more people to drink wine “bringing goodness to the world” because I really believe in the power of the wine and dine experience where people unplug, gather with family and friends, share stories/victories/defeats and personally connect.

What are your “5 Things I Wish Someone Told Me Before I Became CEO” and why. (Please share a story or example for each.)

1. Everything takes way longer than you expect. Each day creeps by and it seems like you add more items to your list of things to do than you subtract. It’s important to pause every once in a while, to look back on all that has been accomplished and give yourself some credit.

2. Don’t waste your energy on people who do not want to work hard or go the mile (forget the extra mile).

3. If your gut says no, say no because you’re probably right. When it comes to hiring, really think about who you want to bring onboard your team: Are they a fit culturally? Will they add value? Do they have certain ideas on product development? Don’t settle until you discover exactly what you want to create matches with what you’ve created.

4. Read the book the Lean Startup — it is a great resource founded on real examples and a very clear explanation about why you don’t have to build the entire product before releasing it into the wild.

5. Being CEO can be a lonely job. Build a team of people and a network beyond that will be there for you even when you can’t pay them to do so.

Can you please give us your favorite “Life Lesson Quote”?

Spoken best by the late Anthony Bourdain and something I’ve lived by all my life (long before he articulated it), “I’m not afraid to look like an idiot.”

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this

Barbara Lynch because of her belief in the art of storytelling and how the meal, the people, the experience all weave together to form a compelling narrative. She has worked extremely hard (without complaint), found her passion, has achieved great success and shares her story with thousands of guests every year. She is a true inspiration!

Gary Vaynerchuk for his liberal use of “colorful” language and his straight forward demand that people stop whining. Having founded the Wine Library, it would be great to have a conversation with him around the topic of how wine and technology can and will intersect, and why the Wine Library shouldn’t go another day without a CorkGuru partnership.

Originally published at medium.com

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