Working from Home with

Dionna Gray

Founder & CEO of Womanish

Chicago, IL

Dionna Gray is currently the CEO and Co-Founder of Womanish, an exhibition produced by Women, for all. Dionna has experience in account management, influencer management, digital marketing, traditional advertising, consultative sales, project management, and business development.

Favorite Farm Animal: Horse

Connect with Dionna

Day In The Life


6:15am - Wake Up & Read

7:00am - Meet maintenance person at Womanish

9:30am - Back to hotel & nap

10:30am - Start full-time job

1:00pm - Drive home & call for full-time job

2:00pm - Womaish After Dark meeting

4:00pm - Continue to work

6:00 pm - Jog

6:15 pm - Shower and get ready for dinner

7:00pm - Dinner with friend

10:30pm - Wind down from day and go to bed


  • Physical Notebook
  • Jira
  • Outlook
  • Phone
  • OneNote
  • Total Expert
  • CRM
  • Zoom
  • GoToMeeting
  • Google Hangout

My name’s Dionna Gray, I am the founder and CEO of Womanish. My sister and I founded Womaish together. We were working on an app prior to this, which was going to be a social platform for women. To promote that app, we were doing events and we found that it was more impactful when people met in person.  We wanted to figure out a way that we could do something really big as an event. 

One day, Danyelle was in the shower and I was washing my face. She was like, “We should do an experiential event.” We started having all these ideas for rooms themed around women. That was January 2019. In June 2019, we met our creative director who’s designed experiences for Fall Out Boy and big names like that. She was able to take our vision and run with it, and it’s been magic ever since. 

In addition to Womanish, I also have a full-time job as the marketing manager for Guaranteed Rate. I manage their West Coast marketing, so I have a lot going on in my day to day. 

Yesterday, I spent the night in a hotel because I live in the suburbs, an hour out from the Womanish space in Chicago. We had an escalator issue, so I had to meet the maintenance person at 7:00am. I know me, and I was not going to be there at 7:00am if I wasn’t already in the vicinity. So, I woke up around 6:15 am and I was 10 minutes walking-distance away.

When I wake up, before I look at my phone, I take a moment to be thankful for whatever is going on in the day. Even in March, which was a dark moment for me. I think part of being successful in life is your perspective on things. I tell myself every day, “Okay. I’m alive. My family’s healthy.” You have to remind yourself every morning to be grateful.  And then I typically read for around 20 minutes. 

I’m a checklist freak. If it’s not on my checklist, it will not get done most of the time. Going into the next day, I have things on my list that I want to get done. So I already had the whole day mapped out and I knew what I had to do. 

After getting ready, I went to meet the maintenance person at 7:00am. Then I had to drive to go get our merch–we had like 24 boxes.

My job starts at 9:00am, but I was like “They’ll be okay for an hour.” So, I headed back to the hotel and took a nap for an hour. I was able to get a late check-out, so I worked from the hotel for a little bit. Then around 1:00pm I finally drove back home. 

While I was driving, I had a meeting for my full-time job on the phone. And when I got back, I had a two hour creative meeting for our after-dark Halloween series with my creative director, Emily Dahlquist, and co-producer, Ashley Wolve. They’re the best of the best of the best of the best. I really wanted to do something cool for Halloween, and I always want to make sure we’re staying fresh and cool so we can continue to engage with people over and over again. They came to the meeting and were like, “We’re going to totally flip this space. It’s going to be so cool.” So I’m super excited for you guys to see it. 

After the meeting, I continued to work until around 6:00, responding to emails and making sure projects were moving through. My day-to-day- work for my 9-5 includes managing my regions marketing initiatives in Jira, answering requests, plenty of meetings, and helping the regions I am assigned to navigate marketing. 

One of my really good friends was in town from LA. It’s important for me to make time for the people that I care about, but sometimes it’s so hard because of my schedule. We were supposed to meet at 6:00, but I was like “Hey, I really have to get my daily jog in.” I went jogging at 6:00, took a shower, and then went out to dinner with her. 

I was like, “Girl, I’m not going to come makeup ready, I’m just coming in my sweater and jeans.” She was like “That’s fine. Me too.” We went to a place called Hooligans and we were there until they closed. Thenwe just sat in the car talking! 

BTS: Setting up for Womanish After Dark (1/3)

At night, I like to read my Bible. I’m very faith-driven. This whole thing has been a faith thing. A lot of the people who have done experiential events of this magnitude, they’re billionaires and millionaires. They come from a lot of money. 

My sister and I did not come from a lot of money at all. We had to take out personal loans to start. We tried to take out business loans, but they don’t really give business loans to minority and women-owned businesses. So lots of the blessings that we’ve had have just been really out of the blue, crazy things. When I read the Bible’s stories, I feel like I learn great lessons about myself as an entrepreneur and my personal journey. It’s the best way to round up my day. 

- As told to Order In. This interview has been lightly edited and condensed for clarity

BTS" Setting up for Womanish After Dark (2/3)
BTS: Setting up fro Womanish After Dark (3/3)

Rapid Fire

What was your first job?

I was a cashier at Best Buy. It was very, very good training for how to interact with a wide variety of people.

If you could create any tool, what would it be, and how would you use it?

I have so many different things going on with two different teams, so being able to go into one platform and see all of my projects from Womanish and my actual 9 to 5 job would be really fantastic.

If you’re having a bad day, what do you do to get yourself motivated?

So, I have actually had a really rough year. I lost one of my best friends and different things like that, in the midst of trying to build Womanish. At first, I didn’t even want to do this anymore. Whenever I’m having a bad day or I feel myself getting sad, I take a sec to recognize it. I’m like, “Okay, Dionna. You’re feeling sad right now. You can stay sad and not be able to move on, or you can say that it’s okay to feel sad, and then think of something new that will make you feel happy.” That’s my thought process, and it works for me.

What professional advice would you give anyone?

Try to be the better you, every single day. I think that there’s been so many times where I messed up or I did something wrong, whether it was with Womanish or in my career. You’re just like, “Oh, I suck,” or whatever, but it’s okay! You will fail, you will always make mistakes, but it’s just about trying to be better than who you were yesterday. If you didn’t get anything on your checklist done yesterday, just be like, “Okay.” Analyze, “Why didn’t I do this?” Because for me, a lot of the time it was that I didn’t write it down or that I was on Instagram too long. Just seeing why you failed and improving upon that the next day will really take you further.

Outlandish Career Goal

I actually want to found a bank franchise.