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Stephani Estes: “Embracing change across all of society”

Embracing change across all of society: everyone is dealing with so much change in this moment. And while change is never easy, I often feel like change begets change. Once we start to change one aspect of our life, sometimes making other changes doesn’t feel as disruptive. We’re at a turning point in our society […]

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Embracing change across all of society: everyone is dealing with so much change in this moment. And while change is never easy, I often feel like change begets change. Once we start to change one aspect of our life, sometimes making other changes doesn’t feel as disruptive. We’re at a turning point in our society not only in how we handle the pandemic, but also how we handle the systemic racism that has plagued this country for more than 400 years. I’m hopeful that as we look to change how we work and live in the shadow of a pandemic, we will also start to think differently about how we create a more equitable and just world.


The Covid-19 pandemic has affected nearly every aspect of our lives today. Many of us now have new challenges that come with working from home, homeschooling, and sheltering in place.

As a part of my series about how busy women leaders are addressing these new needs, I had the pleasure of interviewing Stephani Estes.

Stephani is senior vice president, executive director of media at the independent advertising agency, Cramer-Krasselt, leading a team of nearly 100 professionals. She has worked with businesses and brands such as Bank of America, Hallmark, Pandora, Disney Parks, Hostess, Edward Jones and many others. Stephani lives in Chicago with her husband and two-year-old twins.


Thank you so much for doing this with us! Before we dig in, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

I had a bit of a “non-traditional” start to advertising. Immediately after graduating from college, I joined Teach For America and taught high school special education in St. Louis for two years. It was an amazing experience and taught me a lot about leadership and building coalitions for success. After Teach For America, I wanted to get back to what I had studied in college — journalism and strategic communications. I started my career in media nearly 15 years ago at Starcom, working on brands like Disney Parks, Bank of America, and Hallmark. Since then, I’ve bounced around the Midwest, working at agencies in Kansas City, Minneapolis, and Chicago. I have been at my current agency, Cramer-Krasselt, for the past 5 years. I started here as the Director of Digital Strategy and have been overseeing media at the agency overall for the past year. The focus of my career has shifted from more “traditional” media planning to primarily digital media, and for the last several years that has extended into more data and technology — which I love, because the industry is always changing and there’s always something new to learn.

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

Two years ago, I was promoted to senior vice president at my agency. It was something that I had been working towards for years. Two weeks before I was promoted, I found out I was pregnant. With twins. It was something else I had been working towards for a long time, since my husband and I were one of the one in eight couples who struggle to get pregnant. Suddenly I needed to figure out how to handle two new roles, both important and valued to me, at the same time. Navigating these two roles forced me to do something I had struggled with my entire career — drawing boundaries. Having a work/life balance was no longer an aspirational goal, it was a necessity. Learning to draw those boundaries meant becoming my own advocate and understanding the importance of being present in the moment — whether it’s mom time or work time. Although motherhood is often seen as a liability in the workplace, I think the skills I have gained from this transition are my superpowers. I won’t say it’s always easy or perfect, but being a working mom means knowing what’s important in the moment and acting accordingly. And that’s a skill that comes in handy no matter what you do.

Are you working on any exciting new projects now? How do you think that will help people?

A big focus I have in my current role is fostering a more curious culture within my department. My background as a teacher left me with a passion for developing and mentoring others through continued education — and the great thing about media and technology is that it’s always changing, so there’s no shortage of learning opportunities. Most recently I have been working within my department on knowledge sharing — we have a team of brilliant experts and any time we can tap into that knowledge to educate others, we get the double benefit of developing leadership and story-telling skills in our presenters. I have also been working on larger agency development opportunities, like teaching others about our technology stack and participating in our agency’s diversity, equity, and inclusion committee. The work I get most excited about is when I can tap into my teaching skills and help others grow.

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?

I have been fortunate enough to have many people who have helped me get to where I am today. And I have two stories of people who were instrumental in my path:

When I started working on Amy Engel’s team at Starcom, I was figuring out how to navigate a complex client and a difficult team dynamic. I came to her often for support and guidance — and I often arrived at her door frustrated and feeling lost. Amy would always ask me the same question, no matter whether the issue was client or personnel related — what is the problem we’re trying to solve? That simple question was so powerful at helping me focus and identify not only what I needed to do, but how she could help support me on that path. It’s a question I find myself asking my team now — and I’m thankful for Amy’s leadership in helping me learn to focus my problem solving.

I first met Chris Wexler when he interviewed me for an associate media director role at Campbell Mithun. He ended up hiring me, then leaving the agency a few months later — leaving me in a new city at a new agency without a manager. Fortunately, we stayed in touch, and when I was looking for another opportunity, he encouraged me to apply for the Director of Digital Strategy role at C-K. Despite the fact that my background was more integrated and that I hadn’t yet served in a digital-only role, Chris advocated for me and my experience. And after I was hired in that role, his sponsorship of me at the agency led to many opportunities for me to demonstrate my leadership and strategic skills. I’m thankful for that sponsorship, as it opened the door for my current role.

The Covid-19 pandemic has affected nearly every aspect of our lives today. Can you articulate to our readers what are the biggest family related challenges you are facing as a woman business leader during this pandemic?

Since the start of the pandemic, the biggest family related challenge has been caring for my 2-year-old twins while working from home full time. I’m fortunate to have an equal partner in my husband, but he also works full time. The hardest part for me — and I’m sure many other working moms can relate — is having to face my working mom guilt directly every day. Normally, my twins are at daycare while I’m at the office — I’m able to focus on work, and even though that guilt exists, I can redirect those feelings into my work. Now, I have to actually see my daughter’s disappointment (usually in the form of a tantrum) that I can’t read to her because I have to be on a conference call. Pulling the double-duty of full-time parenting and full-time working is difficult and exhausting enough, and the addition of the emotional toll of mom guilt is insult to injury.

Can you share what you’ve done to address those challenges?

I wish I could say that I have the answer — but I don’t! What has helped me is finding time to be present with my kids when I can. This is the most uninterrupted physical time I have had with them since maternity leave, so I try to lean into the positive aspects of that. We take walks in the morning before I “go to work”. I try to log off at 5 so that we can play outside before dinner. I can’t say that resolves the challenges, but it does help me find some moments to enjoy every day.

Can you share the biggest work related challenges you are facing as a woman in business during this pandemic?

There’s a quote I keep seeing that really sums up my work challenges well — women are expected to work like they don’t have children and parent like they don’t have to work. It’s challenging to have to say no to a morning meeting because I have to get my kids fed while my husband is on a call with Hong Kong. It’s hard when your kid starts screaming when it’s your turn to share updates in a department head meeting. Many of my colleagues are not parents, which makes it harder. For the most part, my agency has been understanding of the issues that parents are facing. But being “on” as a parent and a busines leader all day long is exhausting.

Can you share what you’ve done to address those challenges?

The most helpful thing for me was splitting the day into shifts with my husband. I watched the kids in the morning while handling email and taking a few calls here and there while my husband worked in our office downstairs. We switched at lunch, and I saved my meetings and work that needed more attention from me for the afternoon. It wasn’t always perfect — sometimes I had 9am client meetings — but it gave us a routine of sorts that helped make the day more predictable. And of course, I was fortunate to have enough control over my calendar to make that work. There are a lot of women who aren’t in that position who still have to make it work.

Can you share your advice about how to best work from home, while balancing the needs of homeschooling or the needs of a family?

There are a few things that have been best practices for me and my family:

Overcommunicate with everyone — I think clear communication is important all the time, but it’s especially important now. I am clear with my team on when I’m available and when I’m not. I’m also clear about when I’ll be able to respond on projects — sometimes that’s not until after my kids are in bed. That overcommunicating also goes for my partner — every morning we go through our calendars and talk about what’s flexible and what’s not. I even extend that to my kids and let them know when mama has a call coming up and when she can play. During a really uncertain time, I think being clear in communication can help ease some of those anxious feelings.

Make a schedule, but plan for changes — my husband and I divide the day into shifts. He works in our office downstairs in the morning while I multitask at work and watching the kids. We switch at lunch and I focus on work downstairs for the afternoon. We both try to manage important meetings or heads-down work time around this schedule. But unfailingly, things change — so we identify what’s flexible and what’s not upfront so that we can tag team effectively.

Be kind with yourself (and others!) — I read somewhere that we’re not “working from home”: we’re at home, during a crisis, trying to work. I have been working to give myself some grace on my productivity and my parenting. I can’t do everything that I was doing before, and that’s okay. And I try to apply that empathy to my team, both at work and at home, as well.

Can you share your strategies about how to stay sane and serene while sheltering in place, or simply staying inside, for long periods with your family?

I’m an introvert by nature, so staying home for long periods of time hasn’t been as hard for me as it has been for others. But even I need to get out of the house from time to time! I have found unusual solace in weeding my vegetable garden. It’s a nice way to have some alone time outside. Beyond that, I try to keep the same schedule every day. I get up at the same time I was before working from home and I follow the same morning schedule of getting ready for the day. That helps me feel like I have some sense of normalcy — plus I can have my breakfast in peace before the kids wake up!

Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the coronavirus pandemic have understandably heightened a sense of uncertainty, fear, and loneliness. From your perspective can you help our readers to see the “Light at the End of the Tunnel”? Can you share your “5 Reasons To Be Hopeful During this Corona Crisis”? If you can, please share a story or example for each.

A friend shared a quote from Arundhati Roy recently: “Historically, pandemics have forced humans to break with the past and imagine their world anew.” There’s a lot more to that quote, but the idea of imagining our world anew is one way I am trying to stay optimistic. I think this moment in time is full of change — and we do have reasons to be hopeful.

  1. A new way of working: it’s amazing to me how quickly companies adopted remote working arrangements — not because I didn’t think remote work was possible, but because the idea of working remote was not something widely accepted by corporate culture. And while I personally do look forward to the day when I can participate in a brainstorm with my colleagues in person at a whiteboard, I’m hopeful that this experience will open up greater flexibility in work arrangements moving forward — because we all know now that it’s possible to work effectively remotely.
  2. Greater empathy for working parents: for working parents, the pandemic made it impossible for us to “hide” our parental status for the sake of productivity. Everything — from frustrated e-learners to hungry toddlers — was on display for our colleagues. I’m hopeful that this experience will create more empathy in the workplace for work/life balance — and that’s not just beneficial for working parents, that’s good for all of us.
  3. Embracing change across all of society: everyone is dealing with so much change in this moment. And while change is never easy, I often feel like change begets change. Once we start to change one aspect of our life, sometimes making other changes doesn’t feel as disruptive. We’re at a turning point in our society not only in how we handle the pandemic, but also how we handle the systemic racism that has plagued this country for more than 400 years. I’m hopeful that as we look to change how we work and live in the shadow of a pandemic, we will also start to think differently about how we create a more equitable and just world.

The Arundhati Roy quote ends like this: “It is a portal, a gateway between one world and the next. We can choose to walk through it, dragging the carcasses of our prejudice and hatred, our avarice, our data banks and dead ideas, our dead rivers and smoky skies behind us. Or we can walk through lightly, with little luggage, ready to imagine another world. And ready to fight for it.” I’m hopeful that we will all be traveling lightly through this moment and that we’ll all emerge from this with a greater focus on what is really important.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Energy rightly applied and directed will accomplish anything.” (Nellie Bly)

As a kid, I read a lot about Nellie Bly and it was a big part of why I wanted to study journalism. I think about this quote often when trying to solve a problem — how can I apply and direct my energy in the right way — whether that’s learning, listening, asking questions, or charting a plan — to get where I want to go?

How can our readers follow you online?

You can find me on LinkedIn.

Thank you so much for sharing these important insights. We wish you continued success and good health!


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