Creating Smiles: An Interview with Cheryl DeSantis, Chief People & Diversity Officer for SmileDirectClub


“When I was growing up, I was very close with my dad, who was always my coach in sports,” remembers Cheryl DeSantis, Chief People and Diversity Officer for SmileDirectClub. “Every day he would ask me, ‘Who did you make smile today?’ That was his way of opening conversation. And so, when I had the opportunity to hold a leadership position at SmileDirectClub, I knew that I had to jump at the chance to join in the business of making smiles, all while honoring my father’s very important question.”

DeSantis’ father passed away in 2010, and she considers her work today a tribute to him, and a way to bring him along with her in life. 

“It truly feels like I have him with me every day, and that feels really special,” DeSantis added. 

DeSantis recalls that as she was coming up in the world, she always thought ‘why not?’ when offered a new job or experience. 

“I knew one day that these little puzzle pieces would make a beautiful picture and at the time I didn’t know what that picture would look like,” she says. “I went from PR, to advertising, to corporate communications to HR. And a lot of people might go, ‘I can’t do that, because I’m trying to go upwards, and if I take that sidestep, I may not get there.’ But for me, it was all a beautiful patchwork that helped me get to the C suite level.”


SmileDirectClub is dedicated to democratizing access to oral care. DeSantis reminds us that many times people don’t have access to an orthodontist. An estimated 85% of people worldwide could benefit from orthodontic care, yet less than 1% receive it each year, with cost being the biggest issue. Additionally, over 60% of counties in the U.S. do not have access to a dentist or orthodontist. SmileDirectClub is here to help more people realize the life-changing potential of a smile they love through a convenient and cost-effective smile journey.

“We know that when someone feels good about their smile, it can change the way they see the world and the way people experience them in the world. So, we’re in the business of creating smiles. We’re at 1.7 million and growing,” she says.  “We’re giving people the ability to experience the life-changing potential of a smile and the confidence and self-esteem that comes with it.”


DeSantis believes that a mission-oriented company always generates a higher level of real engagement, and she argues that’s the case for SmileDirectClub. She also says it’s often a fun place to work. 

“I see a difference in our Team Members in bringing smiles and fun and am reminded that it’s part of our brand,” she says. “Our brand is not this serious corporate entity. We’re serious about our mission, but we bring fun and energy and excitement internally as well as externally.”

She points to the fact that the people agenda for 2022 includes an effort to bring happiness, joy and fulfillment to everyone that works for the company. 

“We do this through big ways and little ways,” DeSantis says. “We have all company happy hours, we have Lunch and Learns, we have networking where people can connect with the leaders and talk about shows and books and where people can be real.”


Most companies experienced a transformation during the beginnings of the COVID pandemic. SmileDirectClub was no different, and had to figure out how to navigate both corporate workers in offices as well as people working in shops and manufacturing. 

“The strategy included a couple of things, it included development for remote leadership, because not everyone has had the opportunity to create a remote culture,” DeSantis says. “We did some training on empathy, to make sure people could connect and really understand empathize and connect with one another during these challenging times.”

The company quickly realized that remote work also came with its challenges, and encouraging balance became a key priority. Many initiatives were created to empower Team Members to take time off to celebrate the moments that matter most. This also applied to the workday with the launch of a ‘Creating Space’ memo that included protection for the lunch hour and a pledge for fewer meetings after a certain point on Fridays. 

“We moved quickly to maintain the connectivity of Team Members, because that’s what you initially lose,” she says. “We have a session called Live with Leadership, where anybody can dial in and ask questions of senior leadership. This helped us maintain connection points throughout the year. We also got more rigorous in our town halls to make sure that we were always communicating with our Team Members.”

SmileDirectClub also turned their focus on making sure that Team Members still felt seen and valued. To this end, the company put forward retention and engagement plans to make sure all Team Members are met where they are in their career path and in their life.  

“The biggest thing I’ve learned is that one size does not fit all,” DeSantis tells us. “What one team is struggling with, another team might find as a blessing, so we created these detailed engagement plans for every team.” 

The transformation to a flexible and remote workforce was in the end achieved through keeping the company’s core attributes of living their truths, being collaborative, and staying laser focused on the customer throughout the pandemic. 

“It’s been a great evolution for us,” she says. “In April of 2021, we announced that we were going fully virtual, and that was a big boost. We’re proud to be an early adopter and embrace a flexible work structure. However, we still have an office for those people that want to collaborate in-person, to offer a best of both worlds’ situation.”


As an adopted child, DeSantis says not feeling as if she belonged was a pervasive issue. This stirred a passion in her to insist on working at businesses that offered their Team Members a real sense of belonging. 

“No matter who you are or where you come from, we value our differences and really focus on our similarities,” she says. “What we’ve done at SmileDirectClub is create a cross-functional inclusion, diversity, and belonging council, and we did this to bring everybody together. We wanted to have one council that people can be a part of, because we want to bring those groups together to leverage the power of inclusion versus creating separate groups where you get a good network and you get good mentoring, but you don’t get that outside perspective from others.”

SmileDirectClub’s Inclusion, Diversity, Belonging and Culture Council (IDBC) is both focused and metric-driven to ensure the respect and dignity of Team Members. 

“We’re providing our leaders with conversation starters to really talk about diversity and to bring it into regular discussion. And we’ve seen some really good outcomes,” she says. “Because we’re focusing on bringing people together versus putting in an infrastructure where you still feel separate. You have a seat at the table just because you’re you.”

The company has also been very intentional about hiring local leadership when expanding into new markets. This isn’t always easy with a company experiencing rapid growth. 

“We’re not even eight years old yet,” she reminds us. “We’re still getting our legs under us, but the good news is there’s like leadership buy-in at the top. And when you look at our demographics, we are actually very diverse, naturally. I think we’re diverse naturally because of our mission to democratize access to care. Our internal Team Members really reflect our customer base.” 


SmileDirectClub is excited about the future and will continue to focus on delivering a superior customer and Team Member experience. 

“Every story matters, internally and externally. This year is going to be about making sure every team has career pathing and career plans. We’re continuing to reinforce our Create the Space initiative around finding downtime to recharge, reengage, maybe even do some volunteering,” DeSantis says. “We’re launching our employer brand, which is called Let’s Make Smiles Happen Starting with Yours, and we’re going to continue to focus on engagement and retention and making sure that we bring fun.”

Overall, she says, people want purpose and respect. 

“Team Members want to work for a company where they will feel supported and invested in,” she adds. “It’s important to celebrate and grow each Team Member’s talents, skillsets and passions to continue to help them grow, and in-turn, your company will grow; that’s the magic formula.”