39. Gina Winstead (she/her) – Director of Member Engagement, Director of Diversity and Inclusion, Keystone Innovation Zone Coordinator, Pittsburgh Technology Council

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“We need to continue these uncomfortable conversations, build strategies and take action to develop strong allies.”

Tell us a little bit about what a typical day looks like for you.

My days are always different and I love that about my job. Working for one of the country’s oldest tech associations connects me to over a thousand different companies that I get to know and help promote. I generally start my day by listening to the Calm App to get my mind right, then walking my two dogs, Dill & Pickle, and finally carpooling to work with my partner to the Northside.

Much of my time is spent in the field and in my email. You can find me meeting with tech companies and educational partners to help them with business development, marketing/communications, talent attraction/retention and government relations. I always bring my diversity, equity and inclusion lens to the table to help Pittsburgh’s tech ecosystem include everyone. One meeting I’ll be holding a conversation with the CEO of Covestro about diversity and inclusion work and the next meeting I could be helping a new life sciences company that’s developing technology that reduces drug overdoses to apply for the KIZ state tax credit.

I’m a busy body, so I generally have a meeting or networking event in the evening to attend focused around more tech equity issues or a non-profit cause I care about like the Western Pa Conservancy, 412 Black-Jewish Collaborative or WIT PGH.

How do you stay passionate in your career?

I spend a lot of time meeting other people who are underestimated in their areas of work. These people keep me challenging myself and hopeful. It’s so important to have a group that’s a sounding board for your ideas and that truly believes in you no matter what your background may be.

Did you have a traditional path into tech (i.e.: CS/IT degree transitioned into tech job)?

Not at all. All of the indicators of a techie were embedded in me from a young age, but the access, representation and opportunities weren’t there for me. I have a bachelor’s of science degree in psychology and eclectic background of nonprofit and for-profit experience. A great referral from an old coworker and my business development background helped me break into tech.

Are there any apps, software, or tools you cannot live without?

Spotify. I create playlists for every trip I take and mood I have or want to have. I’m obsessed with a few podcasts, particularly the podcast Techish, Recode Decode, TechVibe Radio. For fun I listen to Ear Hustle, 2 Dope Queens and The Ron Burgundy Podcast. 

It’s common knowledge that women and femmes often face obstacles in the tech industry based on their gender. Have you ever had to deal with this type of experience and if so how did you handle it?

Yes. As a woman of color in tech, I understand that biases have shaped my advancement and placement in the industry. I find that I have to boast about my age and work experience to be taken seriously and not objectified. In other ways, I still have certain privileges and I’ve become a voice for those among us who can not stand up against systemic racism, sexism, homophobia and other discriminations in the industry. I continue to lend my ear to folks looking to advance in their careers.

What’s your favorite thing about being a part of the #womenintech community?

The momentum is so contagious and international creating potential and opportunities to connect women to endless resources. I can post something on LinkedIn or Twitter that another #womenintech will notice in another city, state or country and I’ll instantly find a new support system from women and men built because of our shared experiences and empathy.

If applicable, how have you given back to the WIT community?

I put in a lot of my spare time getting to know and encourage other women in tech, but my favorite part is sharing the message about authentic intentional inclusion through public speaking at summits, on panels and moderating conversations between unlikely advocates in the industry. We need to continue these uncomfortable conversations, build strategies and take action to develop strong allies.

What is a piece of advice you would give to others wanting to or currently pursuing a career in tech?

To those wanting to pursue a career in tech: Take the leap of faith. Don’t wait until you have all of the technical skills that you think you need. You would be surprised how much you can learn on the job. Start showing up at WIT PGH events and make some friends who share the same passions and can keep you motivated.

What I would tell my old self: Shut that Imposter Syndrome down! You belong here.

Tell us about a time you felt extremely accomplished in the past year.

Having my event I coordinated for the Inclusive Innovation Summit selected as the kickoff event featuring the Mayor of Pittsburgh and Backstage Capital was pivotal to my career. It lead to my role as the first-ever Director of Diversity and Inclusion at the Pittsburgh Tech Council. I get to help bring people to the table that didn’t even know there was one or how to get there. It’s the most rewarding part of my job.

How readers can support you:

Support me by supporting each other. Seek an ally and be an ally. I can’t do this work alone. If you know of an organization that needs help with their business development or diversity and inclusion initiatives, connect us. Follow my moves and events on LinkedIn and Twitter.

Favorite quote if you have one?

“Be the woman that fixes another woman’s crown without telling the world it was crooked.”



Twitter: @GinaEstelle

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