Ali Caravella

CAREER AND LEADERSHIP COACH

About Ali

I’m a certified leadership and career coach with a deep background in consulting, HR, and talent strategy—and a lifelong passion for helping women lead fulfilling lives at the intersection of career and caregiving. Before launching my own coaching practice, I held senior roles in global HR leadership and recruiting strategy, supporting leaders and teams through growth, change, and disruption.

I’m also a certified Fair Play facilitator and co-creator of the Fair Play Method certification program with Eve Rodsky and Hello Sunshine. I work with clients navigating inflection points—whether that’s returning to work after leave, leading through burnout, or recalibrating identity and ambition through motherhood.

Personally, I’m a mom of two daughters, a dedicated daily walker, an avid tennis player, and a passionate home cook (soup is my love language). I live in Stamford, CT and find joy in 1:1 meaningful conversations, being in nature, and supporting women through moments of transition and transformation.

CORE VALUES

Agency, Authenticity, Curiosity, Experimentation, Freedom, & Love

What is it like to work with me?

Clients describe my coaching style as equal parts strategic, grounded, and deeply personal. My goal is to create a space where women can be fully honest about what’s working—and what’s not—with zero judgment. I bring empathy and clarity to the table, offering support AND actionable guidance. Together, we name what matters, untangle complexity, and build new patterns that support personal and professional growth.

Whether we’re working on confidence, communication, career direction, or creating a more sustainable rhythm at home and at work, I meet you where you are and help you move forward.

Why this work?

Because this is the work I needed. And still need.

Like many of the women I coach, I had to learn (the hard way) that ambition and caregiving don’t have to cancel each other out, but they do require support. Too many women feel like they’re the only ones struggling, doubting, juggling, or questioning. I know the power of being seen, supported, and given the right tools at the right time—and I’m committed to helping other women access that power too.

A BIT MORE

Education & Training

  • BS Mathematics, Vanderbilt University

  • Leadership Coaching Strategies, Harvard Extension School

  • Motherhood & Work, Stanford Continuing Studies

  • Certified Fair Play Life Facilitator, Fair Play Policy Institute

  • Certified Holistic Health Coach, Institute for Integrative Nutrition

  • Certified Change Management Professional, Prosci

“Life is a laboratory. Be curious, experiment boldly, and observe without judgment.”

- Raphael Rakowski (my dad 🙂)