Career Profile: Monica Gray, DreamWakers

Monica Gray is the co-founder and CEO of DreamWakers. Under her leadership, DreamWakers has expanded to 30 states in less than two years. DreamWakers works with thousands of students in low-income communities. Monica Gray recently received the Founding Cville Award and the Toyota Mothers of Invention Award. Her work has been recognized in Newsweek, The New York Times, and The Washington Post. A long-time education advocate, she contributes to Huffington Post Education, and writes about social justice, entrepreneurship, and education innovation. Monica received a BA in american studies, and an MPP with a focus in education policy from UVA.

DreamWakers is a nonprofit organization that harnesses the power of free video technologies like Skype and Google Hangout to bring exceptional career speakers into public school classrooms, inspiring students across America. A wide segment of America’s youth lack exposure to career opportunities and dynamic professionals. Using Skype and Google Hangout, working professionals from places like the State Department, White House, Google and Nike connect with students in live, interactive flashchat sessions.

Career Profile: Monica Gray, Dream Wakers

Monica Gray, Co-Founder and CEO of DreamWakers

What is DreamWakers’ mission?

DreamWakers harnesses the power of free video chat services to bring diverse and dynamic speakers into high-need public school classrooms.

For background, a wide segment of America’s youth lack consistent exposure to career opportunities and dynamic professionals. Studies show that this gap widens as children progress through school and life, and profoundly impacts their educational and professional opportunities. Furthermore, less than half of employers actually believe young people are prepared for work. Yet two-thirds of employers have little to no interaction with schools! At DreamWakers, we take advantage of free and existing technologies – like Skype and Google Hangout – to help bridge that divide between public schools and our rapidly changing workforce. Our goal is to expose students to future career opportunities and exceptional real-world professional role models. Since launching two years ago, we’ve successfully connected thousands of 4th-12th grade students in over 50 cities with vetted volunteer speakers who work in both the public and private sectors at places such as Apple, CNN, JetBlue Airways, Makerbot 3D Printing, The State Department, and The White House.

How did you come up with the name, DreamWakers?

The name is based on an Aristotle quote: “Hope is a waking dream.” By shining a light on the depth and breadth of career choices available in the “real world,” we want to awaken hopes and dreams within students across the country — particularly those in low-income areas — about the opportunities that lie ahead after graduation.

What are your responsibilities as CEO and cofounder of DreamWakers?

Every day is different and the list shifts and changes as DreamWakers grows – which is exciting! When you’re a CEO entrepreneur, you need to be your own communications and marketing team, IT specialist, HR department, and strategic planning committee. I’ve never had a boring day and I’m constantly learning new skills.

For example, at the moment, I do everything from managing our social media channels to pitching DreamWakers to corporate sponsors to planning strategic partnerships with schools and meeting with local government representatives. At an operational level, I’m involved in the coordination of each one of our flashchats and personally work with the schools and speakers to make sure the events run smoothly. Looking at the big picture, I’m also responsible for financial and hiring decisions, as well as planning the strategic goals for our team. I want to ensure that we are on target to scale at a pace that allows us to continue to provide high-quality flashchats (our term for the 40 minute video sessions) and make sure the experience is a win-win for our busy volunteer speakers, our dedicated teachers, and most importantly, for the public school students we serve.

Career Profile: Monica Gray, DreamWakers

You were recently named Toyota Mother of Invention in association with the New York Times and Women in the World — congratulations — what was that process like?

Thank you, we are thrilled to be honored! To be honest, this award came as a happy surprise to my co-founder Annie and me, and we couldn’t be more excited. We didn’t submit any applications for consideration, and had not received a lot of media attention around DreamWakers and our mission to date. We have been focusing all of our attention on the product and growing our platform, and truly thought that we were relatively unknown outside of the schools with whom we worked. So you can imagine our astonishment and genuine joy when we were contacted by a Women in the World rep about being chosen for this award. It is inspiring validation about the work we are doing; work we look forward to scaling so that we can bring flashchats to more and more students across the country and, one day, around the world!

What has been your proudest moment from your career so far?

My high school in Staunton, Virginia asked me to deliver the commencement address last year and speak about the work I was doing with DreamWakers. This was special to me for a number of reasons. Not only do I have fond memories of walking those halls as a student, but my hometown teachers were the very first to believe in me and support DreamWakers when we had no other users prior to our official launch. We hosted our earliest flashchats there, and they continue to be among our most active program participants.

It was a unique honor to stand at that podium, in front of many of the same teachers who had me in their classrooms a decade ago, to speak about the vision and goals we hoped to meet with DreamWakers, to reflect on growing up in that community and how profoundly it had impacted me. It was an extraordinary experience to be able to share my excitement and passion about entrepreneurship and the transformational power of public education with those in my hometown, and especially with the young graduates who will be moving the next generation forward to do even bigger and better things in the world.

Monica Gray Portraits, NYC July 2016. Photography by Margarita Corporan

What has been the biggest challenge and, on the flip side, the biggest reward of starting DreamWakers?

Every worthy endeavor has its challenges, but I never thought ours would have to do with wifi! A surprising number of schools we work with across the country have unpredictable and spotty wifi, making it hard to host uninterrupted streaming video. We navigate around the issue, but in 2016, wifi was the last thing we expected would cause headaches!

On the flip side, I would have to say the biggest reward is seeing the faces of the students during flashchats. The way they light up with excitement and interest, and how you can literally  see the lightbulbs go off in their heads as the speakers talk about their careers. It’s incredible to see that immediate positive impact and know that those students will walk away with a spark of inspiration about what their future might hold.

It’s also rewarding to receive positive feedback from our users. For example, a veteran teacher posted on Facebook last week that hosting a flashchat with her English class was a highlight of her career. Likewise, a speaker sent an email to me earlier in the month saying that his experience hosting just one DreamWakers flashchat with a group of students in one of the poorest communities in D.C. inspired him to continue to give back, and he had since signed up to volunteer at his local Boys & Girls Club in Philly. We also sometimes receive thank you notes from students, which is awesome. A 7th grader named Ashley wrote after her flashchat with two Latino entrepreneurs: “The experience was amazing because it was extremely informing, as I, myself, strive to one day become an entrepreneur.”

Hearing from the people we serve like this makes me believe more and more that DreamWakers has the power to create such a positive ripple effect for everyone involved – students, teachers, speakers, and the DreamWakers staff. It is rewarding to be a part of every single day.


What is on your desk right now?

If you walked into my office right now, you would find: a MacBook Air, Starbucks grande Pike Place coffee, sticky notes, a white board divided into four quadrants (Important Now, Important Later, Not Important Now, Not Important Later), and a hard drive holding a copy of every flashchat we’ve ever hosted. We lovingly refer to it as the “dream drive;” having all of the flashchats in one place is a constant reminder of where DreamWakers started, where we are today, and the excitement of where we’re heading.

What are you reading right now?

Some girlfriends and I recently started a book club, and we’re reading The Goldfinch — so far, I love it! Nonfiction-wise, I’m reading Just Mercy Just Mercy: A Story of Justice and Redemption by Bryan Stevenson. I also just bought a book of smoothie recipes this morning called Superfood Smoothies Superfood Smoothies to go along with a new blender…I definitely need more fruits and veggies in my life so I’m hoping this will help!


What is your career advice for other young professional women?

My advice is to stop asking everyone for advice! Instead, ask yourself. You have an an inner compass and it’s meant to be followed — looking around for validation or direction will never work as well as looking inside at what makes you tick and provides you with meaning.

When I was first building DreamWakers, the idea of subletting my apartment to a stranger on Craigslist, packing up a rental car and moving from DC to a basement in Charlottesville, VA to work at UVA’s startup incubator probably seemed nuts to a lot of people. It meant that I had to take up side jobs like waiting tables and babysitting just to pay rent. Was I nervous about how it would all play out? Of course! Honestly, the experience was a lot harder and more isolating than I expected. But I knew deep down that it was exactly what needed to happen to take DreamWakers from vision to reality, and I believed deeply in our mission. That said, I often had to take a step back and remind myself of my personal goals. When I had doubts and wondered, “Am I doing the right thing here!?” the answer revealed through inward reflection and journaling was always that, what perhaps seemed crazy to others (or on LinkedIn!) made sense for me, because DreamWakers fused together each one of my personal and professional interests: public service, entrepreneurship, education policy, and media. I knew enough about myself to realize this was the direction to point my sails, and that it was up to me to chart my own course. So I went for it – and I have to tell you, it’s been the best decision I ever made and my greatest professional adventure yet.

So my advice is basically you do you! Know yourself, trust your gut, and have the determination to make your dreams a reality.

Images courtesy of Monica Gray Portraits, NYC July 2016. Photography by Margarita Corporan and Monica Gray.

15 Responses to Career Profile: Monica Gray, DreamWakers

  1. Katie says:

    This is such an interesting interview, thanks for sharing!


  2. Bella B says:

    Such a great read, I loved learning about Monica!! She is so inspiration!!

  3. Love this career series, such a great read!

    Kayla || Keynotes from Kay

  4. Jenny says:

    Such an inspirational lady! This series is my favorite.

    xoxo, Jenny

  5. Annaliese says:

    What an incredible company and mission! Using technology that already exists to better schools in need.

    xoxo A

  6. Laura B. says:

    Great post!

    Laura B. |

  7. Anna says:

    I absolutely love this series! It’s so inspiring!
    -Anna |

  8. alex says:

    Great interview! So inspiring!!

  9. Tori says:

    Wow what an amazing organization! Education is so so so important.


  10. DreamWakers sounds incredible! Thanks for sharing!

  11. Wow! I love people who use their power and influence to help people who can’t necessarily help themselves. When I was in college, I worked at a camp that assisted kids at at-risk middle and high schools that had little funding. They attended this camp for free and they were able to learn about the importance of higher education. It was such an incredible experience, and I love that Monica Gray utilizes free services to provide similar experiences to underprivileged students.

  12. Amy says:

    This is such an inspiring read! Love reading about #GirlBosses, it motivates me to work that much harder to one day be as successful as them!
    Amy | Pastel N Pink

  13. This is so great! Harnessing the benefits of technology to bring better education and opportunities to youth is amazing.

    -Meagan | Love by Meagan

Comments are closed.