We were lucky to catch up with Shannen Stewart recently and have shared our conversation below.
Alright, Shannen thanks for taking the time to share your stories and insights with us today. One of the most important things we can do as business owners is ensure that our customers feel appreciated. What’s something you’ve done or seen a business owner do to help a customer feel valued?
Last year for our Annual Holiday Party we decided to dedicate the entire event to showing our members ( clients) how much we appreciated them. The women who are members of Heels & Handshakes are high-achieving professionals. As much as we encourage and advocate for taking self-care days, we also know our members and that they are always serving others. It was a no-brainer for us to dedicate our Holiday Party to surprise and delight our members. We hired a company to provide chair massages, brought in a nail salon for a station for Holiday nail art, hired an artist to make on-the-spot custom pet ornaments, and ended the evening with gifting over $2000 in door prizes.
I think this made an impact because we didn’t give our members a branded gift as a thank-you. A true gift is an object, a gift card, or something the end client wants to utilize or redeem. Our members don’t need a branded coffee mug to say thank you for your business.
In our case, we provided activations and luxury experiences for our high-achieving professionals who may not have the time to schedule for themselves. The feedback was this was the best Holiday Party they had attended and our members felt appreciated.
I would encourage companies to plan an event or an activity once a year or quarter, depending on budget, to surprise and delight their top clients to show them appreciation.
One year, we rented out a movie theatre for our members. Other ideas include bringing in a singer-songwriter, or renting out a bowling alley or somewhere with games and activities depending on the demographic of your top clients.

Shannen, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
For those who are unfamiliar with Heels & Handshakes, we are a membership for Women in Business, Entrepreneurs, and their Allies providing in-person meetings, educational workshops, resources, and referrals to put your best heel forward in your personal and professional life.
I started Heels & Handshakes 10 years ago because I was looking for a community of like-minded women who were career-driven in the hospitality space. Fast forward to 2020, we realized the importance of diversifying our membership portfolio and now we serve women in all sectors. Women in Tech, Women in Banking, Women in Finance, and Women in Hospitality.
If you are looking for help with transactions in your business, a tribe to support you or you are a transplant to a new city and need resources, we are a great way to get connected.
We are headquartered in Nashville, TN, and have expanded to Alabama, Illinois, and Texas.
We are community-driven, and referrals and business come second. I am proud that as an organization that prioritizes relationships we have tracked annually over 2 million dollars in B2B revenue. This proves that people work with whom they like and trust.
Heels & Handshakes stands out from other organizations as we create a safe space for women to foster genuine connections. We empower our attendees at every meeting to share a S.T.R.U.T. this stands for Share, teach, recognize, uplift, and toot your own horn. This encourages and gives our members a permission slip to share their accolades in a room full of supportive women.
Our Mantra is, “Surround yourself with Women who would drop your name in a room full of opportunities.”

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?
A lesson I have had to unlearn recently is the narrative that “failure isn’t an option.” I have wasted a lot of time, energy, and money by playing the soundtrack in my head. In reality, every successful CEO and Fortune 500 company will disagree and encourage you to FAIL FAST and FAIL OFTEN.
I pursued projects that were bleeding money because I didn’t want them to look like a failure when I would have been better off cutting my losses learning from those failures/lessons and making sure to put plans in place to never repeat them again.

What else should we know about how you took your side hustle and scaled it up into what it is today?
Yes, Heels & Handshakes was my side hustle for seven years before I took the business full-time in 2020. I was working for a corporation as their Director of Strategic Accounts while I built my dream business on the side. The irony and lesson I learned is that “ready is a lie.” I had a strategic plan to leave my full-time job in February of 2020 and then life had other plans with the Pandemic one month later. The silver lining during the Pandemic was that people realized the importance of having a community and my business did thrive during a very difficult season.
The success of my business, Heels & Handshakes didn’t happen overnight. I built the community for seven years by hosting in-person events, consistently once a month, and tracking our referrals to show the ROI of the membership. In January of 2020, I launched a membership and we had 120 women sign up in three weeks. This was a key indicator that there was a need for us. In the first year of membership and in a Pandemic we had 220 women. In the second year, we had 300 members and in the third year, we expanded to four different cities and are on track to generate 2 million dollars in B2B revenue within our membership.

Contact Info:
- Website: www.heelsandhandshakes.com
- Instagram: https://www.instagram.com/heelsandhandshakes/
- Linkedin: https://www.linkedin.com/in/shannen-stewart/
Image Credits
Shannen Stewart headshot provided by Tausha Dickinson Event photos: Jillian Hawkins Photography Divine Images MK Event Photo

