About Penney Leadership

We’re your resource for career clarity.

Clear, compassionate career coaching and strategy from mission-driven leaders who have been in your shoes.

The world of work needs more mission-driven leaders like you… but I know firsthand that pursuing your purpose and defining your direction can be complicated to figure out on your own. 

When your head and your heart are in your work, this strength sets you apart — but it can also get lonely. For you, the typical career advice about climbing the ladder, leaning in, and buckling down isn’t the right fit. 

If those old career rules feel exhausting and you’re craving a different way to approach your work, then we have a whole lot in common, and you’re in the right place.

How I discovered my professional identity – to help you do the same. 

MY JOURNEY FROM NONPROFIT LEADERSHIP TO PENNEY LEADERSHIP

I’m Carole-Ann Penney, certified professional coach, career strategist, and Founder of Penney Leadership. For 10 years, I’ve coached mission-driven leaders like you on their path to design a meaningful career that aligns with who they are.

But I wasn’t always so clear on my own purpose. A decade into my professional career, I woke up every weekday with a pit in my stomach. I had done all the things I thought I was supposed to do, climbing the ladder of my nonprofit career through 7 job titles in 10 years. My organization did meaningful work and my career looked great on paper, but something was still missing. 

In time, I tuned into an inner knowing that started as a whisper and steadily grew to shake me by the shoulders in the form of burnout: I am meant to create my own meaningful and impactful professional path—and to help others to do the same.

With that realization, Penney Leadership was born, and has never stopped growing since. As we’ve evolved from a one-woman business into a wholehearted practice with an active community, our mission has only deepened. We’re here to support mission-driven leaders across all sectors who feel called to make a difference and want work to be much more meaningful than just a paycheck. 

If you’ve been feeling alone in your career challenges, you should know: there are a lot of leaders like you out there, and many share your same questions. Penney Leadership is here as a resource for you to get the individualized support you need and to welcome you into a community of mission-driven professionals navigating their own paths. I’m so glad you found your way here. 

Meet Your Career Coach

For purposeful and practical coaching.

Carole-Ann Penney, CPC
Founder | Strategic Career & Leadership Coach | Speaker | Leadership Trainer

  • Certificate in Professional Coaching, Institute for Professional Excellence in Coaching (iPEC) 

  • Certificate in Nonprofit Management & Leadership, Tufts University

  • B.A. in Education Studies, Brown University

  • Senior HBR Facilitator for Harvard Business Publishing’s Corporate Leadership Development programs

  • Instructor at Electives

  • Contributor to Harvard Business Review

Carole-Ann Penney, CPC (she/her)

I founded Penney Leadership to help mission-driven professionals navigate their work and lives with purpose and resilience.

For 10+ years, I’ve coached over 200 emerging and established leaders just like you through their career path challenges, transitions, and successes.

Through 1:1 and group coaching, interactive workshops, group facilitation, and speaking engagements, I’m passionate about sharing practical, purposeful tools and perspectives that you can immediately implement to advance your work. 

If you’re feeling uncertain, discouraged, or like something within you is calling out for more, I’m here to be your thought partner and guide.

As a Certified Professional Coach, I offer you all the resources and tools you need to become the confident leader of your own life and career. And as a formerly burned-out but “successful” leader who had to dive deep and design her own path, I understand. I’m here to help you uncover your authentic leadership style and create your own meaningful career path that aligns with who you are.

Beyond the Penney Leadership community, I mentor emerging leaders through Brown University’s Women’s Launch Pad, Social Enterprise Greenhouse, and the Institute for Nonprofit Practice. 

When I’m not coaching (or listening to career podcasts and reading leadership books!), I'm developing the most important emerging leaders in my life — my kiddos Avery and Eliana.

Fun Facts

Plus, we’ve got a squad of experts on speed dial who have your back.

Meet our go-to trusted partners for…

 Brushing up your application materials

Wendy Wallace

Resume, Cover Letters, and Interview Prep Coach, Wallace Consulting
Wendy’s got you covered with the support you need to put your best foot forward.

wwallaceconsulting.com

Empowering women of color

Cynthia Pong, J.D.

Career Coach & Founder, Embrace Change
Cynthia Pong, JD, is the founder of Embrace Change, an award-winning career coaching and consulting firm specializing in working with mid-career women of color.

embracechange.nyc

Going out on your own

Michelle Ward

Business Coach, 90 Day Business Launch
Since 2008, Michelle has helped hundreds of women launch their service-based dream businesses so they can become their own boss.

90daybusinesslaunch.com

Uncovering your life purpose

Melissa Carvalho, MA, RYT

Holistic Life Purpose & Career Coach, Melissa Carvalho Coaching
Melissa coaches women shaping their 30’s to gain clarity on their career path, empowering them to make a meaningful impact and fulfill their sacred purpose.

melissamcarvalho.com

Transitioning into retirement

Hannah Anderson

Transition Coach, Golden Thread Coaching
Hannah offers deep listening and practical planning for all of life’s transitions, from a new stage of life, employment or retirement, relationships, or losing a loved one.

goldenthreadcoaching.com

Negotiating your next move

Alexandra Dickinson

Negotiation Coach
Negotiating doesn't have to be scary. Alex will give you step by step negotiation guidance. You’ll learn proven strategies to achieve and exceed your biggest goals. 

alexandra-dickinson.com

Values-driven coaching for mission-driven leaders

Penney Leadership is fueled by…

  • Connection

    Real connection is at the heart of Penney Leadership, always bringing together people, resources, and ideas.

  • Growth

    Leadership is a practice, not a destination, and growth along the way is exciting and essential.

  • Curiosity

    We have a voracious appetite for learning new ideas and perspectives via articles, podcasts, and books, and love to share insights with the Penney Leadership community.

  • Opportunity

    We believe in the practice of seeing possibilities everywhere, taking initiative, and trusting ourselves to create our own opportunities rather than waiting for someone else.

  • Purpose

    We're all here to make and express meaning in our lives, both personally and professionally. Penney Leadership is a welcoming and purposeful community for anyone searching for a fulfilling sense of more in their career.

  • Whole-heartedness

    We deeply value showing up as our whole, authentic selves, and making space for others to do the same. Mission-driven work involves both the head and the heart, and this type of care, commitment, and personal investment is a strength.

Commitment to diverse perspectives and individual experiences. 

Each person comes to coaching with unique strengths, values, challenges, and intersectional identities. There are no one-size fits all answers. Coaching is not teaching, advice-giving, or mentoring—instead, I specialize in creating a space and structure that allows you to make your own discoveries that are individualized and meaningful to you.

We all have different experiences based on our intersectional identities. I bring my own identities and lived experiences to my work: I am a millennial, white, heterosexual, cis-gender woman. I’m able-bodied, average body sized, and an English-speaking US Citizen. I am first generation college educated. I’m also neurodivergent, a mom, and a small business owner. All of these identities inform who I am; some are upheld as the “norm” of the dominant culture, while some position me closer to the margins. I am committed to reflecting on where I hold proximity to power through my identities, and how that shapes how I show up as a coach and facilitator. 

Penney Leadership welcomes clients who embody all dimensions of difference: race, gender identity and expression, sexuality, religion, age, class, nationality, disability, parental status, veteran status, citizenship status, education, size, and more.

As your coach, I recognize that your lived experiences are different from my own and from the other leaders I work with. Our identities and the unique relationships we have with them give us each a unique set of insights, expertise, and knowledge. They also mean that we perceive and are perceived by the world differently.

I am committed to curiosity—continually seeking to understand the evolving perspectives and language related to power, privilege, and how our identities impact our experiences at work, as well as learning about what it means to move through the world with identities I do not myself embody. That includes reading books and articles, listening to podcasts, professional development workshops, and connecting with colleagues and thought leaders that expand and challenge my approach.

I am always open to feedback on how I can make my offerings more inclusive and welcoming to all. I’m committed to staying humble, correcting my mistakes, and holding myself accountable as I continue learning. I continually strive to build my toolkit of resources that will serve the wide variety of leaders I work with—even if that means referring them to another coach who can better understand their identities and needs. If you have any thoughts or resources you want to share on this topic, please contact me here.

Ready to tag us in as your resource for career clarity?

Let’s team up so you can get in the driver’s seat of your career with confidence.

  • Career Coaching

    Through single-session or longer-term coaching, you’ll clarify your vision, navigate what’s next, and craft a career path that’s meaningful to you.

  • Leadership Coaching

    Craft your personal Strategic Leadership Compass to transform your future—and confidence—as a leader.

  • Corporate Coaching & Training

    Elevate your organization and transform your leaders with customized coaching & training for organizations.

  • Speaking

    Treat your audience to modern, meaningful professional development and personal growth by booking a speaking engagement.