Jeannie Assimos of Way.com: “Let it go”

Let it go. When you walk out of the office and back into your personal life, let all the stress and concerns of the day go. There have been times when I wasn’t able to leave the stress behind, and my health suffered, and ultimately, my work also suffered. So it’s important to have a […]

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Let it go. When you walk out of the office and back into your personal life, let all the stress and concerns of the day go. There have been times when I wasn’t able to leave the stress behind, and my health suffered, and ultimately, my work also suffered. So it’s important to have a personal identity and separate your work and home life.


How does a successful, strong, and powerful woman navigate work, employee relationships, love, and life in a world that still feels uncomfortable with strong women? In this interview series, called “Power Women” we are talking to accomplished women leaders who share their stories and experiences navigating work, love and life as a powerful woman.

As a part of this series I had the distinct pleasure of interviewing Jeannie Assimos.

Jeannie Assimos has been an enthusiastic leader in the content arena for nearly two decades, beginning her career at Entertainment Tonight, followed by a VP of content position at online dating OG eHarmony. She currently is Head of Content at tech startup Way.com, which she says is the most exciting role yet.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your childhood “backstory”?

Sure! My backstory is that I’ve always loved storytelling. When I was 7 years old, I was stapling paper books together and writing these little stories, mainly about scary subjects, much to my mother’s dismay. Things like “The Evil Sister” or “The Bad Babysitter,” complete with illustrations. I think I got the love of the horror genre from my dad, who loved Vincent Price. We would watch scary movies together every weekend.

Can you tell us the story about what led you to this particular career path?

My uncle worked in the entertainment industry as a foreman building movie sets. Since I was already creatively inclined, I knew I wanted to be in that world in some context. The ability to reach a lot of people through a creative outlet was absolutely what I wanted to do. I would tell everyone I was going to be an editor someday, even thought I had no idea what that was. But, as the power of intention illustrates, I ended up worked as Managing Editor at Entertainment Tonight.

Can you share the most interesting story that happened to you since you began your career?

I think it has to do again with the power of intention. It was at Entertainment Tonight that a coworker gave me the Deepak Chopra book, “The Seven Spiritual Laws of Success.” It really resonated with me, and I began reading a lot of his books. A few years later, we interviewed Chopra after Heath Ledger passed away — as he was one of the last people to speak with the actor. When I landed at eHarmony, I found myself sitting in Chopra’s office interviewing him about relationships. This was such a thrill for me on a personal as well as a professional level, and taught me that what we focus on in life, we truly can create. In this case, it was an invaluable connection and experience.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Self-Belief. Whether I was interviewing celebrities on the red carpet at Entertainment Tonight (with very little experience!) or sitting down to do 100 satellite interviews as a spokesperson at eHarmony, the common denominator in all these situations wasn’t that I had done these things before, but that I believed I could.

Focus. The ability to walk into the office and focus all my energies on my job has been an immeasurable asset. I listened, learned, and took my environment in completely. I was told that because of my focus on understanding the brand of eHarmony, I was given the sole responsibility and additional role of hiring and managing the pr teams.

Loyalty. I am loyal to those I work with and loyal to the brands I am working for. That is always a huge priority in any task I am completing. Is this helping the brand or hurting it? This is how I earned the unofficial title as the “voice of eHarmony.” When your coworkers have trust in you and your decision-making, that is also a game changer for your experiences and opportunities at a company.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. The premise of this series assumes that our society still feels uncomfortable with strong women. Why do you think this is so?

I feel like there are still those in society that feel women are supposed to be amenable, and supportive, and sweet. It’s an antiquated way of thinking. Of course, we can be many of those things in certain contexts, but we are also intelligent leaders who can be just as tough and have proven we have earned a seat at the executive’s table.

Without saying any names, can you share a story from your own experience that illustrates this idea? I was known for being outspoken at executive team meetings. At first, one of the CEO’s found it amusing. Eventually, he started listening to what I had to say, and some of his own perceptions shifted in a positive way. He soon had me leading TV commercial production for the company.

What should a powerful woman do in a context where she feels that people are uneasy around her?

I definitely think you need to know how to read the room. I could say just be yourself, but that is not how I have achieved success. With some groups of people, I have had a softer approach.

What do we need to do as a society to change the unease around powerful women?

I think we are getting there. The more examples of successful female leaders there are out there in every industry, the better it is for everyone’s comfort levels. So, article series just like this one are instrumental!

In my own experience, I have observed that often women have to endure ridiculous or uncomfortable situations to achieve success that men don’t have to endure. Do you have a story like this from your own experience? Can you share it with us?

I absolutely have endured this. I’ve had former bosses tell me they’d love if I wore skirts more often, no joke. I’ve dealt with sexual harassment at two former companies. I have never allowed anyone to make me feel intimidated. I just put them into the antiquated category and maintained my focus on kicking ass at whatever I was doing.

In your opinion, what are the biggest challenges faced by women leaders that aren’t typically faced by their male counterparts?

Exactly what I mentioned above. It is far too common. It can be very disheartening. But I do feel that the awareness since #metoo has truly been a blessing and helped a lot to raise awareness.

Let’s now shift our discussion to a slightly different direction. This is a question that nearly everyone with a job has to contend with. Was it difficult to fit your personal and family life into your business and career? For the benefit of our readers, can you articulate precisely what the struggle was?

I have had relationships that have absolutely struggled due to my demanding career. I’ve had partners who didn’t understand my work ethic and weren’t on the same page as I was when it came to priorities. When I worked at ET, I had to get up at 4 am for work, and went to bed around 9 pm. My partner at that time complained constantly, even ridiculing me when I would be falling asleep at 8:30 pm. That relationship eventually ended, largely because of this. The one thing I’ve learned is to find someone with similar values. I am in a relationship now where my partner completely gets the dedication to my career, and he is completely ok with it, because he is the same way.

What was a tipping point that helped you achieve a greater balance or greater equilibrium between your work life and personal life? What did you do to reach this equilibrium?

I actually eventually left ET because of a lack of work-life balance. This was after ten years of working there. That was how I achieved equilibrium. Sometimes you have to make really hard choices in support of your wellbeing. I took a risk, and the eHarmony job landed in my lap three weeks later. It turned out to be the best decision I could have made.

I work in the beauty tech industry, so I am very interested to hear your philosophy or perspective about beauty. In your role as a powerful woman and leader, how much of an emphasis do you place on your appearance? Do you see beauty as something that is superficial, or is it something that has inherent value for a leader in a public context? Can you explain what you mean?

I always try to look my best, because I just feel more confident when I have taken the time to put effort into my appearance. As much as appearance shouldn’t matter and the work skills should, I find that it really does make a difference. Of course, beauty is completely superficial, but you can’t deny that it matters in our society. I would say overall it’s helped me more than it has hurt me. But I also think being kind to everyone is just as important as looking great at work.

How is this similar or different for men?

Men obviously aren’t held to the same standards of beauty as women in most industries. I can’t imagine feeling comfortable wearing shorts to work every day! But I would think that men also feel better when they put themselves together and put effort into their appearances.

Ok super. Here is the main question of our interview. Based on your opinion and experience, what are the “Five Things You Need To Thrive and Succeed as a Powerful Woman?” (Please share a story or example for each.)

Courage. Have the courage to use your voice, take risks, to sit at the table, share your ideas, the courage to fail, and the courage to learn from others. Have the courage to say yes, despite being terrified. There are countless times I was afraid to do things. When I first joined eHarmony, they asked me to do a satellite media tour for tips on being single during Valentine’s Day. These were live interviews happening all over the country. I said yes, and still can remember when the tour was over, how proud I was of myself for pulling it off.

Boundaries. Saying no can be challenging for women. But I learned it is crucial to have boundaries when it comes to your work and the quality of that output. The more you say yes to tasks, the more they will pile on. So it’s extremely important to know exactly what your priorities are. I was once asked to work overnight shifts at Entertainment Tonight. I knew that if I did this, my work the next day would suffer greatly, as would I! So I graciously declined the request, and that boundary was set.

Passion. Make sure you have a passion for what you are doing. When you have that, you have won. Your work is better, your attitude is better, your days are much better. I honestly lost my passion at eHarmony the last year I was there, as the business went through huge leadership changes. I knew that it was time to make a change, and that’s exactly what I did. Now I am loving going to work again and that is priceless to me.

Let it go. When you walk out of the office and back into your personal life, let all the stress and concerns of the day go. There have been times when I wasn’t able to leave the stress behind, and my health suffered, and ultimately, my work also suffered. So it’s important to have a personal identity and separate your work and home life.

Be adaptable. One of the biggest reasons I’ve seen people not succeed in the workplace is because they had a very rigid idea about what their job was (and held onto it for dear life!). Just as life changes, work can change, needs change, business plans change, so the more adaptable you can be the better. I went from managing 6 content sites at eHarmony, until the team decided they wanted to sell them all off and get out of the content publishing business. I pivoted over to brand work and pr, and that helped the team greatly.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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