You’re a woman in tech who feels left behind. You want to navigate work culture with confidence, claim what you want, set boundaries against what you don’t want, and own your value.
Curious? Check out my Befriending Dragons YouTube channel.
Don’t find yourself. Make and remake yourself. — Cindy Gross
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 bully, a harasser, bias and inequities, or something you know is wrong but can’t quite name – you know your workplace isn’t working for you and you want a new path forward.
Cindy has a way of sifting through the noise of logistics and emotions, to get at the heart of an issue. She invests heavily in the experience, and success, of her clients — and her investment is obvious through the entire coaching experience. She is a powerful coach, and she has the ability to notContinue reading “dr. sarahlloyd, PhD | The Equity Whisperer”

Cindy leverages her lived experience and coaching expertise to help people better understand issues from the perspective of people whose lives are different from ours. I participated in an anti-racism group that Cindy ran in 2021, and I looked forward to the insightful and honest discussions in every session. The program opened my eyes inContinue reading “Julia Goldstein | Communication that Supports Businesses on their Sustainability Journeys”


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. Schedule a free consult to learn more about my 5-month VIP Uplevel Your Career program.
Cindy Gross
She/her | ex-techie SQLCindy
Delaware & Cherokee citizen
survivor of workplace bullies and harassers
We customize our 5-month VIP Uplevel Your Career program to your style, needs, & goals so you can:

Navigate Work Culture with Confidence
- Know what keeps you feeling confident
- Gain a well-rounded understanding of 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
Program Features
- 10 private sessions to identify, shift, and transform your mindset and habits
- Online learning for your career, leadership of self, and DEI growth
- Quick check-in sessions for immediate needs
- Peer interactions to multiply learnings
- Client portal to track your insights and partner on accountability
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.
Cindy’s Origin Story
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.