Uplevel Your Career

Are you a woman in tech who feels left behind? Are you smart, capable, and motivated yet losing the joy in your job? Do you want to navigate work culture with confidence, set boundaries that work for you, and claim your value?

Staying in tech is draining you. You no longer feel like you’re in control of your own career.

Now what?

It’s unfair. It hurts. It feels personal. Whether it’s a micromanager, a bully, a harasser, bias and inequities, or something you know is wrong but can’t quite name – you know the way things are going isn’t working for you and you want a new path forward.

White woman with red hair cut in a shoulder length bob. She is smiling and wearing a multi-colored scarf with a teal coat while leaning against a brick wall. Logo of a dragon with the words Befriending Dragons.

Imagine Your Life When You

Navigate Work Culture with Confidence

  • Know what keeps you feeling confident
  • Name and say your strengths and opportunities
  • Uncover how you want to show up during conflict and uncomfortable conversations

Claim What You Want for Your Career

  • Remove roadblocks to requesting what you really need
  • Plan how to align your work with your purpose, values, and goals
  • Develop a circle of supporters so you’re not doing it all alone

Set Boundaries Against What You Don’t Want

  • Learn ways to recognize when & how your boundaries, values, or purpose are not working for you
  • Know how to identify & act on your non-negotiables
  • Practice meaningful responses when someone makes you uncomfortable

Own Your Value and Raise Your Voice

  • Have new ways to demonstrate your leadership to yourself and stakeholders
  • Be persistent and clear about your own needs
  • Listen differently to your inner critic so you believe in your power and self-worth

Cindy Gross

I left a 25-year tech career to start Befriending Dragons when reporting harassment led me down a path of discovery, systems thinking, adaptive leadership, and community focus. I help you discover your own path forward to a successful, fulfilling career. Together we’ll listen differently to our internal dragons – our dreams, fears, anxieties, instincts, patterns, habits, hopes, and expectations. We’ll befriend these dragons, pay attention to their signals as the valuable insights they are, and choose how to move forward with them.

Intrigued by the short excerpt of this guest appearance? Listen to the full “Unleashed Potentials Podcast” episode hosted by Bernadette Desir.

Smiling white woman with red hair, blue shirt, brown jacket

How did I get here?

After 25 years in corporate tech I was burned out. I couldn’t think. I couldn’t make decisions. I couldn’t cope with anything. So I took a lot of time off and slowly, so slowly, worked through the trauma of reporting harassment at work, of being involved in a pay inequity fight, of so much bias and so many white male shaped bars. I realized what was missing was connection, community, and values-based leadership. So I became that. The connector. The community nurturer. The coach who really gets systemic inequities and wants to lead with relationships. I befriended all those dragons, and now I help my clients THRIVE.

If you’re looking for someone who is direct, safe, empathetic, supportive, and focused, you’re in the right place. My clients say I have an “extraordinary impact” and “amazing insight,” create safety by being vulnerable and fully present, sift through noise to surface the gems, and infuse a race + gender equity perspective into my listening & questions.

Would you like to show up at work feeling confident and valued, with people honoring your boundaries? Let’s explore how we can work together.

What My Clients Say

“Simply OUTSTANDING – my favorite session of the conference!” | ”The applause for ALL the #DataWIT speakers would be DEAFENING in person, but I think it’s possible @CindyGross would’ve brought down the damn house.” | “Best session ever!” | “Whew, @CindyGross is closing this #DataWIT session with heavy truths.” | “One of the best presentations […]

Speaker Raves

My recent private coaching sessions with Cindy were a game-changer for me. Cindy is a fantastic coach for women in tech. She truly understands the challenges we face, from navigating work culture to combating biases. With her guidance, I learned to see different options without changing my current situation. Cindy helped me gain confidence and […]

Josephine Bush | Principal Database Engineer & Data Platform MVP

Curious about my working style and techniques? Check out my Befriending Dragons YouTube channel.

Don’t find yourself. Make and remake yourself. — Cindy Gross

Cindy Gross

She/her | ex-techie SQLCindy.
Leadership Coach, Personal Strategic Advisor, Race + Gender Equity Expert, Keynote Speaker.