Our Bios

Meet the people powering PeopleCap.

Meg Crosby

Principal & Co-Founder

meg.crosby@peoplecap.com | Linkedin

Meg is a recognized thought leader in People Strategy. Meg co-founded PeopleCap Advisors in 2012 to help organizations unleash their full potential through their people. She is a strategic advisor to CEOs, boards and investors, a recognized thought leader in People Strategy, and enjoys asking tough questions. She is also an Operating Partner with SSM Partners, a growth equity investment firm focused on software, services and healthcare. Prior to PeopleCap, Meg’s 20-year career in human resources established her as an expert in organizational culture, people strategy and organizational growth. She has worked for companies of all shapes and sizes including for a small tech startup in Los Angeles as a sole HR practitioner and at Google leading acquisition integration.

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Howard Cleveland

Principal & Co-Founder

howard.cleveland@peoplecap.com | Linkedin

Howard is a coach and trusted advisor to CEOs, executive teams, and senior leaders. In his roles as a Labor & Employment attorney, growth advisor, and certified leadership coach, Howard has partnered with leaders for over 25 years to help them understand and unlock the strengths of themselves, their teams, and their organizations.

Howard serves leaders whose circumstances have temporarily outpaced them. Many of his clients are:

  • in the midst of significant personal or professional transitions
  • struggling to meet the current expectations of their position
  • struggling to gain traction
  • in complex, fast-changing situations
  • having difficulty getting their team to perform
  • struggling to stay at the right level and delegate
  • not comfortable holding their team accountable

Howard serves as an experienced thought partner and confidential sounding board to help leaders gain clarity, confidence, and a clear path forward that is aligned with their personal and professional goals and values.

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“Howard sees strengths in me I don’t always see and has helped me see and appreciate myself more fully. Sometimes, when I lose confidence in myself, I call Howard to borrow some of his.”

Natalie, Director

“Howard is an excellent coach. His presence is of genuine partnership where you feel honored, respected, and supported. I’ve worked with a lot of coaches over the years as a leader. Howard is different. He can see things others haven’t. He has a sense of when there is something behind the something.”

Gail, Founder

“As a seasoned leader making a career shift was really challenging. Howard helped me see some of the stories and beliefs I was holding onto. Letting those go gave me a completely new perspective, built my confidence, and allowed me to see options I never would have let myself consider.”

Teresa, Vice President

“It’s been amazing. Howard is incredibly easy to talk to and asked really thought-provoking questions. I would recommend Howard 100% – a 1000 times over. He has helped me tremendously, and I can’t thank him enough.”

Merissa, Director

“You helped plant in my heart and in my head a new perspective. I am relieved from uncertainty and have gained confidence in what I know and what I can do. I hope you can help other people the way you helped me. It is priceless. It really is priceless.”

Mihaela, Director

“I have worked with many coaches before, however, not one of them was able to listen to, understand, and truly see all circumstances from a Bird’s-eye view like Howard does. What I find most valuable is how he shows up very authentically, and most importantly for me, genuinely he wants to help and how much he loves his work, which is all priceless to me.”

Julia, Entrepreneur

“Howard’s approachable demeanor and relatability stand out. He openly shares his own experiences—the highs and the lows—when relevant, offering valuable lessons from both successes and areas for improvement. This transparency adds depth and authenticity to the conversation.”

Lynn, Manager

“In our sessions, I find the freedom to be unapologetically vulnerable, expressing myself without any fear of judgment. Howard brings a wealth of experience to the table. His guidance is grounded in real-world business acumen and life wisdom. His coaching has been an invaluable asset in both my business and personal life.”

Marissa, Founder/CEO

“Howard is excellent. Great listener. Very authentic and comfortable to talk to.”

Ann, Director

“What I appreciate the most about Howard is his balance between support and challenge, pushing me to stretch beyond my comfort zone while providing unwavering encouragement. Howard created a safe space for me to feel comfortable being open. Howard has the amazing ability to sense the right time to speak up and let me be in the moment with myself.”

Elina, Executive Coach

“Howard’s partnership with our leadership team has been incredibly valuable. Howard created a space where we felt comfortable candidly exploring the issues most important to the team.”

Lisa, President

“Working with Howard illuminated the unique value of my experiences. He helped me understand how to leverage these strengths to elevate my work, advance my career, and support others more effectively. The time I spent with Howard didn’t feel like formal coaching sessions; it felt like genuine, meaningful conversations. Yet I always walked away with valuable insights and practical next steps that I could immediately apply.”

Elif, Executive

“Howard’s questions inspire deep thinking. I could rely on Howard to offer insight as to what he was seeing and then pose a unique question that causes me to totally reorient my way of thinking about the situation in a way that was different than what I have experienced in other coaching experiences. He wasn’t afraid to say the hard thing which invited exploration from a different lens.”

Jessica, Manager

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