From Attorney to Media Company CEO: Sarah Wilkerson

Sarah Wilkerson forges her own path: Attorney to Media Company CEO

Sarah Wilkerson’s story starts out in a way that is all too familiar. Professional military spouse is hindered by the different state licensing rules and looks for a career alternative. Finding something creative she makes a new career for herself. But in the case of Sarah Wilkerson, an attorney who found that practicing law while her active duty husband served in the JAG corps was near impossible, there’s a successful twist, she’s now the CEO of a multi-million dollar company.

Some Military Spouses wear their status like a name badge, visible in all contexts. Others are not secretive about it, and indeed are proud when asked, but their careers bear no intersection with the military or the military space. Wilkerson is one of those people that we need to hear about. She has helped grow a company, with it ending up on the Inc. 5000 list four times as one of the fastest growing companies in the US, while moving every 1-2 years with her active duty servicemember.

Click & Company: From small online Community for Female Photographers to Multi-channel media Company

In 2008, photographer Kendra Okolita founded Clickin Moms, a warm and supportive online community for women to cultivate and share their love for photography. The membership organization revolutionized the photography industry as the first and largest company to embrace female photographers of all levels, from hobbyists to professionals.

Today, Click & company is a multi-channel and multi-media social network for photographers. Their mission is to empower photographers of all levels to capture life beautifully in both their personal and professional endeavors, to make flexible, quality photography education and mentoring accessible, and to maintain a supportive community for continuous learning, sharing, and growth. Click & Company is a privately held company, with an audience of 2.5 million inclusive of membership, students educated, click away attendees and magazine subscribers. It was honored at Inc. 5000 four years in a row and has achieved 5 million in revenue.

Sarah Wilkerson’s journey to being the Chief Executive Officer of Click & Company, a multi-channel media company, began in 2006, with a desire to pick up a camera and learn how to use it. She joined an online community, now with thousands of members, Clickin Moms, and found a group of creative women who challenged and inspired her. She quickly found herself teaching and learning alongside other women.

A familiar tune with a different ending

Wilkerson has been a military spouse for 13 years, and is also a mother of four children. The complexity of combining the different aspects of her life are not lost on her: “It is a lot to juggle” she admits freely. While geographically distant from her parents, they are a huge source of emotional support. While it helps that the whole Click & Company team telecommutes, PCS moves every couple of years are still challenging. Wilkerson has found frank conversations with her service member helpful in trying to make sure they are on the same page: “I prefer not to move overseas and prefer to be as close to the east coast as we can for time zone management. But the reality is that deployments with four kids are difficult.”

Sarah Wilkerson says, “I found it impossible to pursue a legal career and be a military spouse. I needed to find a way to challenge myself intellectually and business wise.”  “I Needed something that was mine” says Wilkerson. “When you marry into the military, it gets turned on its head.  Even being able to move with ease can still make it a challenge to find a job.“ She found that having an area of her life with a lot of creativity was helpful – intellectually and emotionally.

Like for many of us, Wilkerson decided to learn a new skill during a deployment. “My husband is amazingly supportive. I bought my first camera during a deployment. He saw this as an investment and told me “this is important to you”.”

Have you had a mentor or influential person in your life who encouraged you?

As she became an informal leader in the online Clickinmoms community, Wilkinson also became friends with the founder, Kendra Okolita, who was the one who eventually brought Wilkerson onto the team at Click & Company as CEO.  Wilkerson helped transform Clickin Moms from a small social community to a media powerhouse in Click & Company.

The company now has an audience of 2.5 million. This number isn’t some made up figure, but is instead inclusive of membership, students educated, Click Away conference attendees, and magazine subscribers. Okolita – founder of ClickinMoms – allowed Wilkerson to push things to the next level. After almost 10 years of working together Wilkerson describes their relationship as a “mutual mentorship.”

If another military spouse or woman is developing a social enterprise what one piece of advice would you give them?

When asked what piece of advice that she would give to a young military spouse who is wanting to develop a professional network she spoke from experience in encouraging us all to “make the most of social interest groups. Making connections online was a gamechanger for me. It has made moves easier.” The key difference for Wilkerson is that “Online relationships help you create continuity, you move to and away from relationships which can help you get through it and help you with professional connections.”

What has been your greatest success?

 Wilkinson is proud of having helped transform ClickinMoms into a company with much larger aims: from a small social community to a media powerhouse: Professionally – Click & Company have become advocates in ways we didn’t expect for women. The company wasn’t founded to be politically active. Sarah Wilkinson admits “This was not an original part of the mission.” Wilkerson says: “Over time we have discovered we do have to fight for this. We were told we were ruining the [photography] industry. We are embracing it because we want women’s voices to be respected…we have brought talking points back to women, to empower women, and lift women up in a way that has been a catalyst for change”

What has been your biggest challenge?

When asked about her biggest challenge, Sarah highlighted the Internal challenges she mentions that sometimes working remotely as the leader is a challenge, because there are times when brainstorming and lunch meetings feel like they could be more effective in person: “We wish we could be closer for events, produce products and education together. It has gotten better, because larger companies are doing this, cloud based infrastructure has improved – like slack and asana. But it’s still a huge challenge.”

How can we all support Sarah Wilkerson’s work?

To support Sarah Wikinson’s work and to find out more, visit For more information about Click & Company, visit & Sarah especially recommends for those that are military spouse photographers. These websites provide online connections and networking, while also providing a place for education in photography and photographic skills.

Click & Company CEO balances military family life with building successful career

I really appreciate that Sarah Wilkerson took time to speak with me. To speak with another military spouse attorney who has found her way outside the legal profession was particularly encouraging! Let’s share these takeaways on social media with a link to this interview:

Takeaway #1: We are embracing [our role] because we want women’s voices to be respected…we have brought talking points back to women, to empower women, and lift women up in a way that has been a catalyst for change”  – @SarahWilkerson CEO of @ClickandCompany 

Takeaway #2: “Make the most of social interest groups. Making connections online was a game changer for me. It has made moves easier.” – @SarahWilkerson #militaryspouse and CEO of @ClickandCompany 

Takeaway #3: Acknowledge both your successes and your challenges – growing a successful company is hard! – @AMBRabe


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Friday Feature: Social Impact Entrepreneur is an ongoing series of interviews where we feature a leader making a difference in their community.