career & leadership coach for women

Nearly 30 years of corporate experience. Two VP titles. An MBA from Michigan Ross. And one very clear mission: helping the next generation of women leaders get where they're going faster than I did.

 

The career behind the LEADERSHIP coach

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I didn't start out as a coach. I spent the better part of three decades building a career in operations, marketing, client services, and community — climbing from early-career contributor to Vice President, leading teams, managing P&Ls, and running programs for some of the best-known B2B brands in the travel industry.

 

Most recently before founding Summer Day, I was VP of Alumni Content and Community at Signature Leaders, where I launched a brand-new digital community platform and designed and led 36 high-impact leadership events. Before that, I spent over a decade at Northstar Travel Group — home to Phocuswright — rising from Director to Senior Director to Vice President, where I led multiple client delivery teams and drove renewal results that consistently exceeded targets.

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What my resume doesn't show: I was stuck at the Director and Senior Director level for nearly a decade. I kept moving, kept delivering, kept getting passed over for the next level — or leaving before I could break through.

 

The thing that changed it was four coaching sessions. I hired a coach to help me with a job search, and within our first few conversations, she named something I hadn't been able to see: leaving as a Senior Director would be yet another lateral move. Again. I needed to push through and earn the promotion first — then decide what was next. She helped me strategize, reprioritize, and reframe what I was actually building toward. I got the VP title. And then I left on my own terms.

 

That experience didn't make me want to become a coach. It made me want to learn how to do what she did — because I wanted to be a better leader for my teams. I went on to build those skills, get certified, and eventually realize I wanted to offer the same thing to other women navigating exactly what I had.

Throughout all of it, the throughline was the same: I see people. I understand problems. And I know how to build the conditions that help both thrive.

 

Why I left the VP track to do this

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When my daughter was in middle school, she wrote a school essay about the gender pay gap and was genuinely appalled. She couldn't understand why women were paid less to do the same job as men. I realized she was watching. And I wanted to do something that made a difference.

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Between 2020 and 2022, I lost three parents to stroke, Alzheimer's, and cancer. I was working full-time in intense senior roles, and while my companies gave me grace, it came at a cost. I was burned out — mentally, emotionally, physically, and spiritually. Watching my parents succumb to illness made one thing crystal clear: what I was doing didn't really matter. Not in the way I wanted it to.

 

So I asked myself what did matter. And then I went out to build it.

 

I founded Summer Day LLC in 2024 to bring together the two things I love most — leadership coaching and community building — in service of the women who remind me of who I was: ambitious, capable, and navigating it largely alone.

I didn't have a mentor. I didn't have a coach. I didn't even know I should be looking for one. That's my why.

 

What I do now

 

At Summer Day, I offer:

 

The Inner Circle — peer advisory boards for early-to-mid career women. Small, carefully curated groups. Real challenges. Expert facilitation. Long-term peer relationships. The kind of support structure most women wish they'd had sooner.

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Leadership & Career Coaching — I specialize in the "broken rung" — those pivotal moments in early-to-mid career when women get stuck, passed over, or simply can't see what's next. I've coached women through job searches, promotions, career pivots, team leadership, and the ongoing challenge of balancing ambition with a full life. My clients land the jobs they didn't think they could ask for. They get the promotions. They stop waiting and start leading.

Community Consulting — I help purpose-driven organizations design and build communities where real engagement happens — the kind that retains customers, deepens loyalty, and turns members into advocates. I've built and launched communities that work, and I know what separates thriving ones from the ones that quietly fade.

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Credentials & education

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• Founder, Summer Day LLC & Inner Circle

• Certified Leadership & Career Coach (CPCC, ACC)

• Certified Enneagram Practicioner

• 25+ years in marketing, operations, client management & community building

• Worked for large global multi-national companies like Starwood & Hyatt down to start-ups like B3 Insights and Signature Leaders

• Been both a job jumper and a long-term employee

• Board Member, Sanger Leadership Center | Women Enabled Enterprises | Ross Women in Business Alumni

• Mentor, Boulder-CU Leadership, Sanger Leadership Center & Ross Women in Business Alumni

• MBA, Ross School of Business, University of Michigan                

• BA, Psychology & English Lit, University of Colorado

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Featured in

• Sanger Leadership Center Announces Appointment of Rebecca Callahan to the Advisory Board — Sanger Leadership Center, University of Michigan

• Where Theory Meets Action: Sanger Supports Leadership Development in the MBA Curriculum — Sanger Leadership Center, University of Michigan

• Right-Sizing Your Career: Strategy, Ambition, and the "Non-Linear" Path with Rebecca Callahan — The Working Mom Show

• Rebecca Callahan is a community builder and career coach for early/mid-career women — The Midst

• Meet the career coach who will help you get your sh*t together — The Midst Substack

 

Let's work together

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I take on a select number of clients and communities at a time — because the work matters and I want to do it well. If you're an early-to-mid career woman ready to stop waiting, or an organization ready to build a community that actually sticks, I'd love to talk.

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Connect with me →