Work with Me

I’m Cindy Gross – the founder of Befriending Dragons and a former techie. I customize my services to YOUR needs.

I know what it’s like to try to fit into everyone else’s models. It’s exhausting and heart-breaking. I figured out so much AFTER I left tech – now I’m here for you so you can choose your own path.

I’m ideally positioned to support Women in Tech. I bring a unique blend of:

  • 25 years in tech – SQL Server MCM, Big Data, Azure Cloud, & Windows.
  • A direct, no-nonsense style that cuts through the BS – I ask the questions others avoid.
  • Deep empathy that keeps me fully present and supportive while challenging you to explore your perspectives, framing, and options.
  • A trauma-informed adaptive leadership style where I model vulnerability and nurture a safe space for you to thrive.
  • Expertise in Diversity, Equity, Inclusion, and Belonging (DEIB) – Certified by the Kapor Center which specializes in the tech industry.
  • My own healing and growth journey.
  • ICF trained and certified coach with 100s of hours of experience – ICF ACC credential, inviteCHANGE Certified Generative Coach (demonstrated ICF PCC level).

That makes me a dragon in a herd of unicorns. Who are you? Who do you WANT to be?

  • Are you a seeker, fully of curiosity about yourself and the world?
  • Are you open to new ways of being and doing?
  • Are you eager to hear and create unexpected reflections, questions, and options?
  • Are you tired of (and from) the exhausting, lengthy process of doing this all on your own?

Close your eyes and imagine the life you choose. Let’s do this together to make some magic happen for YOU!

Your personalized VIP Uplevel Your Career package is designed to meet YOUR goals.

Together we design and build a new pathway unique to you. I’m with you every step of the way.

  • 1:1 time with Cindy to identify, shift, and transform your mindset and habits.
  • Quick check-in sessions and unlimited online interactions for impromptu needs.
  • Accountability via metrics, actions, reminders, and journals customized to your needs.

Are you ready to show up at work feeling confident and valued, with people honoring your boundaries? It’s time to invest in yourself. Schedule your goal setting call now. Live the life you deserve.

Keynote Speaker & Podcast Guest

Does your audience of women in STEM question how to reclaim joy in their work? Do they feel left behind their peers? Do they want to know how to authentically navigate work culture with confidence? I’ve been there. I know how it feels to lose hope, to see attempts to follow the advice of those who already “fit” not work for me. I have stories and answers to bring direction, joy, and hope.

Race + Gender Equity

I understand the intersection of tech and DEIB, especially race and gender equity. I know how bias infuses AI, data science, and data to degrade the quality of products delivered. I offer training, cultural reviews, and coaching customized to your business needs.

Gracious Space Facilitator & Trainer

Gracious Space enables difficult conversations where consensus and pulling in the same direction really matters. It helps us work together for a shared purpose by creating spaces where people sit in a balance of learning, bravery, growth, and safety.

I am certified via Pat Hughes, who co-created Gracious Space for the Center for Ethical Leadership, to train teams to operate with Gracious Space.

Check out my own story in her latest book Creating Equity with Gracious Space. Mention the book when you sign up for one of my packages and I’ll include a FREE copy signed by Pat and me as part the package.

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

Certificates and Credentials

International Coaching Federation (ICF) Associate Certified Coach (ACC)

Leadership Eastside: Adaptive Community Leadership, Racial Equity Adaptive Leadership, Executive Insight – Managing Adaptive Leaders, Board Member, Campaign Coach

Kapor Center: DEIB in Tech

Microsoft Certified Master: SQL Server

ICF ACC badge

inviteCHANGE Certified Generative Coach, ACTP (Level 2) with demonstration of PCC level coaching

UPenn Social Policy: Leadership Strategy for Violence and Abuse Prevention

Gracious Space Certified Practitioner

AAPF: Critical Race Theory

University of Oklahoma BBA: Business + Computing