Cindy Gross
Leadership coach for high-capacity leaders and women in tech
| Hourly rate range | $150 to $240 an hour |
|---|---|
| Focus areas | Women in leadershipBurnout and resilienceTransitions and new rolesConflict and difficult conversationsTech and engineering leadersCareer clarity and purposePromotions and advancementWomen's careers |
| Works with | Women, Executives, Managers, Professionals and Engineers |
| Also coaches | Career coach and Life coach |
| Credentials | ICF PCC; inviteCHANGE Certified Generative Coach; Gracious Space |
| Practice | Befriending Dragons |
Cindy Gross is a leadership coach who helps high-capacity leaders in tech, including women and underestimated leaders. She founded Befriending Dragons and draws on more than 25 years of tech and leadership experience. Her work covers burnout, boundaries, workplace politics and high-stakes decisions. She built the Leadership Navigation System, a structured method for handling friction at work. She also offers workshops and cohorts for organizations that want to keep their top leaders.
What Cindy helps with
Cindy helps leaders who feel worn down by workload, office politics and big changes at work. She works on burnout, boundaries and next career moves.
- Burnout and overloaded workloads after reorgs or layoffs
- Setting clear boundaries at work
- Handling office politics without losing yourself
- Stepping into a new leadership role
- Preparing for tough conversations
- Gaining clarity on career direction and values
- Making high-stakes decisions
- Reducing leadership friction that drives attrition
Who Cindy works with
Cindy works with high-capacity leaders in tech, including women and leaders who feel underestimated in their workplaces. Her clients often face reorgs, layoffs, a promotion, a bigger scope without more staff, or growing politics. She also works with organizations that want to retain and support these leaders.
How Cindy works
Cindy uses the Leadership Navigation System, a structured method for leaders facing complexity and friction in tech. Each engagement starts by mapping the real dynamics around your role. One-on-one clients build decision rules and language for their next blocker. Many people begin with a Breakthrough Session as a fast reset. Ongoing 1:1 coaching is available for deeper support. Organizations can use cohorts or workshops such as the Strategic Boundaries Workshop.
Background and qualifications
Cindy Gross founded Befriending Dragons and brings more than 25 years of tech and leadership experience to her coaching. She holds the ICF PCC credential and is an inviteCHANGE Certified Generative Coach. She also lists Gracious Space training and Leadership Eastside Adaptive Community Leadership. Her work covers one-on-one coaching, cohorts, workshops, circles and speaking for teams, ERGs and leadership summits.
Cindy Gross pricing
Programs and services
- Breakthrough Session
- Individual Leadership Navigation (1:1 coaching)
- Leadership Navigation System for Cohorts
- Strategic Boundaries Workshop
- "I Got the Role... Now What?" session for ERGs, teams or summits
- Workshops, circles and speaking
Cindy Gross reviews
The CoachVouch take
Cindy pairs more than 25 years of tech experience with a structured Leadership Navigation System built for friction in tech workplaces.
Best for tech leaders facing burnout, reorgs or office politics who want a clear strategy and firm boundaries.
Common questions
How much does Cindy Gross charge?
Coaching with Cindy runs $150 to $240 an hour. Message Cindy from this page for an exact quote.
What does Cindy Gross help with?
Cindy Gross helps with burnout and overloaded workloads after reorgs or layoffs, setting clear boundaries at work, handling office politics without losing yourself and stepping into a new leadership role.
Is Cindy Gross certified?
Cindy Gross lists: ICF PCC; inviteCHANGE Certified Generative Coach; Gracious Space.
Does Cindy Gross work with organizations as well as individuals?
Yes. She offers cohorts, workshops, circles and speaking for teams, ERGs and leadership summits.
Where should a new client start with Cindy?
Many people start with a Breakthrough Session as a fast reset. Those who need more can move to ongoing 1:1 coaching.
How do I contact Cindy Gross?
Send Cindy a message from this page. It's free and takes a minute.
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Last updated September 2026. Request a correction.