We believe that helping clients develop the managerial skills necessary to do the job is important but not enough to create the transformation they are seeking. To be a leader, they must also cultivate a fearless willingness to look deeply through self-inquiry.
“The best way to overcome the inevitable loneliness of life at the top may be to connect and mindfully attend to the process that’s already underway – the unconscious sharing that undergirds every relationship.”
Jerry Colonna is the CEO, and co-founder, of Reboot.io, an executive coaching and leadership development firm whose coaches and facilitators are committed to the notion that better humans make better leaders. For nearly 20 years, he has used the knowledge gained as an investor, an executive, and a board member for more than 100 organizations to help entrepreneurs and others to lead with humanity, resilience, and equanimity. Previous to his career as a coach he was a partner with JPMorgan Partners (JPMP), the private equity arm of JP Morgan Chase. He joined JPMP from Flatiron Partners, which he launched 1996 with partner, Fred Wilson. Flatiron became one of the most successful, early-stage investment programs in the New York City area. He lives in Boulder, Colorado.
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Reboot ’s co-founder and CEO Jerry Colonna is a certified professional coach, who draws on a wide variety of experiences to help clients design a more conscious life and make needed changes to improve their performance and satisfaction. He established his coaching practice in 2007. Prior to this work, Colonna was a venture capitalist focused on investing in early-stage technology-related startups.
In 2002, Colonna became a partner with J.P. Morgan Partners (JPMP), which was the private-equity arm of J.P. Morgan Chase, where he co-led the firm’s investments in technology and media.
He joined JPMP from Flatiron Partners. With his partner, Fred Wilson, Colonna launched Flatiron in August 1996. Flatiron became one of the most successful, early-stage investment programs.
Colonna joined his first venture firm, CMG@Ventures L.P. in February 1995 as a founding partner. CMG@Ventures was the first “Internet-specific” venture firm. Prior to joining @Ventures, Colonna worked for ten years for CMP Media Inc. From 1985 to 1993, he served in a variety of roles at InformationWeek, including a three-year stint as its Editor.
Colonna also serves as Chair of the Board of Trustees at Naropa University. Naropa University the only accredited Buddhist-inspired university in North America.
He also serves on the Board of Trustees at the Tibetan Village Project, a not-for-profit, non-political organization dedicated to creating sustainable livelihoods for Tibetans through social entrepreneurship and educational opportunities.
He is also a director at the Good Work Institute, whose mission is to educate and connect a network of local community members and actively support their collaborative efforts to regenerate their places.
The recipient of numerous awards and a compelling speaker on topics ranging from leadership to starting businesses, Colonna has been named to Forbes ASAP’s list of the best VCs and Worth’s list of the 25 most generous young Americans. A graduate of Queens College, Colonna lives in Boulder, Colo.
“There is fundamental shift happening in the way people view work. It’s not just a job or a paycheck anymore. Our work is the expression of our natural gifts intersecting with the needs of the world. This is the purest realization of human potential.”
Khalid is a certified professional coach and founder of Reboot.io. Clients praise Khalid’s insight and empathy, as well as his ability to transform complicated webs of story into simple strings of actionable steps. He works with founders and leadership teams looking to move through change and growth purposefully. His guiding purpose is to empower the people who will build the organizations he wants to see in the world his children will grow up in. Khalid has over ten years experience working in startups, both as a founder and turnaround CEO.
“If we don’t work on our stuff, our stuff will work on us. It will run our lives–and show up in our offices and relationships–until we take the reins of responsibility for our own well being.”
After working in a variety of startups and a life-time of soul-based explorations, Ali helped bring forth Reboot.io in 2014 when she co-founded the company. She knows the ways of soul, savvy, and magic and she has brought those deep skills and her big heart into her work as COO of Reboot. In that role, she executes and manifests deftly, with clarity and grace. More, too, as a coach, she moves with ease from ally to challenger to guide. Her superpower is getting her clients (and her colleagues) to tap into their innermost being, their source of creativity and innovation, in order to bear the rigors of work/life existential challenges. And, all the while, making you laugh from the very core of your belly.
She knows that regardless of what you’re going through, whatever situation you’re in, the most important conversation you can have is the one with your own heart and the most important relationship you have is the one you have with yourself. She helps clients hear the clarity of their own voice and trust their inner knowing so that they can then align their life with purpose and lead from that place. So that you can manifest what it is you are here to do in this lifetime. Creating humane workplaces of safety and connection is an inside job that begins within each of us.
Ali seamlessly and deftly weaves together her business acumen with the innate wisdom of the body, the philosophies of the world’s wisdom traditions, and the way of the horse to help clients find their voice so that they can find themselves. She draws on her more than a dozen years in business as an operator managing projects, teams, and human resources, and developing brands. Before Reboot, she worked with Jerry Colonna to create the life-changing CEO & Founder Bootcamps in the US and abroad.
With a Masters degree in religious studies from the University of Colorado at Boulder, Ali has studied Transformational NLP at NLP Marin, completed the facilitator program at the Center for Collaborative Awareness, and is a certified EQUUS Experience Facilitator in Equine Facilitated Coaching. She is an avid horsewoman. Her popular newsletters on ‘The Art of Being Human at Work’ live primarily at the Reboot Blog but have also been published by spirituality and meaning experience called OnBeing.
“When we’re facing challenges that appear oppressive to our spirit, or thwart our will to achieve, we come to a threshold that, if crossed, can usher us into a new way of seeing ourselves and the world around us. We gain a new stance that we couldn’t think our way into. Leaning into these crossings is to lean into our emerging leadership and humanity.”
Intensely interested in the human experience, Jim guides individuals and organizations through transitions while stepping more fully into their lives. He’s keen to help entrepreneurs and start-up organizations discover their own authentic expression of leadership and the meaningful contributions that come from it. Jim has extensive cross-cultural experience and has worked in settings around the globe. As a speaker and workshop facilitator, he is engaging on topics of leadership, innovation, design thinking and transformative change and has presented in a variety of gatherings and venues including MIT, Yale University, Michigan State University, Berkeley’s Haas School of Business and a variety of community and professional settings.
Jim is a Senior Fellow of the Presencing Institute, offering training and assistance in the application of Theory U – a methodology of transformative change. He is also a teacher of Authentic Leadership and advisor for the new Authentic Leadership Center at Naropa University. Jim has led programs for and is a former governing council member for the Authentic Leadership in Action Institute, is an advisor to Michigan State University’s Doctor of Educational Leadership program, has been a guide with the Animas Valley Institute for over 10 years, and currently co-guides the annual quest for Naropa’s Masters in Wilderness Therapy candidates.
“We have a choice every day when we show up at work. We can choose to dial it in, or we can choose to be radically human, to use work as a means to move more deeply toward who we are. When we choose the latter path, we open ourselves to truly reaching our greatest potential as humans.”
Heather’s sweet spot is at the intersection of entrepreneurship, purpose, and human actualization.
She followed this narrative thread throughout her career, first as an indie bookstore owner, and then as a therapist and coach, before becoming an executive. At Etsy, she was SVP of Members and Community, building and leading Etsy’s member operations, community and policy teams in supporting Etsy’s 20 million sellers, and later worked in an executive role that focused on integrating values into Etsy’s business and culture. She is known as a highly skilled manager, with deep experience growing and scaling large operational teams and developing mindful leaders and cultures. She has a BA in English and an MA in Counseling Psychology.
Heather believes that building a great business or developing as a leader is equal parts art and science, metrics and intuition, idealism and pragmatism, and her coaching honors these dual aspects. She supports her clients in both addressing the operational and managerial aspects of growing a business and the deeply soulful work of discovering one’s identity as a leader.
“Your leadership style reflects your relationship with yourself. When you shift internally, it reflects externally. Every day you make hundreds of decisions based on your set of beliefs. They drive your behavior and shape you as a leader.”
Kate encourages clients to surface their beliefs and the identity that fuels them. With this awareness, the client can expand their choices about their current reality and future. Kate helps them “revise” their internal software to support them in having more of what they want. In fully honoring themselves, the client becomes a catalyst for bringing out the best in those around them. As these leaders change, their companies and teams transform – becoming emotionally and spiritually safe environments that breed collaboration and innovation.
Kate served as a strategic partner across L&D and HR functions within Apple, Tilt and Airbnb on her mission to build teams that ignite authenticity. Her mix of corporate and start-up experience makes her well suited for clients preparing for scale and hypergrowth. A certified Master NLP practitioner, Kate helps clients appreciate the design of the brain and work in alignment with it to drive profound business and personal results.
“From a place of Authentic Self-expression a true leader unfolds. Connecting to deepening rapport with Self changes Life’s unfolding (forever).”
Jen is an executive & personal coach, group facilitator, and certified NLP Master Practitioner. She passionately assists her clients on their path to a more conscious life, fully stepping into being whole. Many clients comment that Jen’s work is so transformative words simply don’t do it justice.
Jen’s corporate executive & private practice experience spans over 18 years of building high performing teams & individuals. Infinitely willing to meet the client wherever they are on the journey, Jen is confident and authentic in style. She leads through “extreme conflict” with clarity & insight which assists in developing a strong culture to support company values, navigating through challenging mergers/acquisitions and communicating through rapid company growth.
Guided by her strong intuition and deep knowledge of the human experience, Jen gets to the core of what “holds the client back” from living the life they want. One of her most gratifying discoveries working with clients is their enjoyment of the work and the continued growth. Jen thrives on being present to those special “ah ha” moments when the clients connection to themselves and life is forever changed.
The form of your life is designed. By you. The process of revealing the seemingly invisible structures that support the form is a profound journey connecting you to the wonderfully meaningful desires you have for yourself and the world. Every day is another opportunity to re-design how you show up on the journey, every day becoming more and more you.
Chris is an executive coach, licensed architect and passionate listener. His training as both a designer and coach informs how he works with clients by endeavoring to understand and hold where they are as valid, which provides a safe place to create what they most want in their personal and professional lives. For his entire career he has been engaging groups and individuals to craft sustainable solutions that are thoughtful and unapologetically beautiful. Chris believes that we are constantly in a state of transformation and learning, he holds a Post-Graduate degree in Alternative Design from Archeworks and a Master Practitioner certification from NLP Marin.
“We all have aspirations, things we want to achieve. I believe the true formula to achieving our goals is already within us, but is often buried under the burden of our daily lives. I am truly privileged to help people unlock the wisdom that they already possess, and define their own unique path to success.”
From first-time jobholders to late-professionals at Yahoo, Google, and Lyft – to name a few – Courtney helps uncover blocks to individual success so her clients walk away with the confidence and pragmatic approaches needed to be more effective leaders. In addition to corporate coaching, Courtney founded her own triathlon club where she coached a membership of over fifty athletes. Prior to coaching, Courtney worked for 15 years in the fields of technology and sports marketing and has held leadership roles at AOL, Handspring and Webroot Software. Her strong understanding of corporate dynamics allows her to coach management teams within challenging, fast-paced environments.
“As leaders, we are a product of our distinct set of experiences, values and obstacles. Lasting change and organizational impact is created when you have the space & support to examine yourself fully in the context of your role as a leader.”
Jeff Riddle coaches high-performing leaders through periods of introspection and evolution. Clients include CEOs/founders of venture-backed start-ups through acquisition, leaders at companies like Facebook, and individuals from all around the world seeking deeply personal guidance. From interpersonal relationships to leadership skills, from optimizing performance to career satisfaction, the work takes different forms. In the end, the result is dramatic transformation of your sense of self and relationship with the world around you both professionally and personally.
After immersing himself in the startup world in both Manhattan and San Francisco, Jeff now lives in the midwest where he is happily married and devoted to his two young children. In his spare time, he is an avid runner, chef, and musician.
“I am passionate about recovering the lost art of listening well. In this culture of “telling” we are driven to make assertions, give opinions, and push messages. Yet humble inquiry is the gateway to true learning. And listening well to another human being is a sacred gift–one that can help bring about transformation in our relationships and in our organizations.”
Andy is an executive coach, group facilitator, and trainer. He leads Reboot’s internal training and development efforts to support our roster of coaches in their own growth toward mastery and finds his sweet spot balancing direct client work with “building the machine” that is Reboot. In addition to playing an instrumental role designing many of Reboot’s programs and offerings (including Circles, 360s, and Team Experiences), Andy has supported individual leaders and teams at many high growth tech companies (including globally distributed orgs and post-IPO firms). He has a special place in his heart for People Ops leaders and early stage CEOs.
Andy has wide-ranging experience as an educator, pastor, startup leader, and as an instructional designer crafting courses for Fortune 500 companies–the common thread through it all has been a devotion to supporting individuals and groups toward growth, authenticity, and effectiveness. He holds a BA in English and a Masters in Education and is a certified coach and NLP practitioner.
“Helping others find the opportunity – for joy, excitement, beauty – and growth within the wild roller coaster ride of entrepreneurship fuels my passion for this work. After all, the goal isn’t to avoid the bumps, it’s to keep our eyes open and our hands up.”
Dan Putt is an entrepreneur and Chief Product Officer for Reboot.io. As a four time founder, Dan understands the ups, downs and terrifying free falls that accompany the startup life. Dan strives to help others bring their best, most full self to every moment. He believes that on the roller coaster ride of entrepreneurship, the goal is not to avoid the bumps, it’s to keep our eyes open and our hands up. Dan holds a degree in marketing from Ohio State University and is an ICF certified coach.
“Creating a workplace that is at the same time human and successful is the future of work. I have seen first hand how so many leaders are yearning for a different kind of leadership culture to take their companies forward and create growth, innovation and success without losing their humanity in the process. How we define and do “our work” is changing and this is the possibility that is there to step into.”
Angela has a commercial background in leading talent functions in hospitality, travel, and technology. For the last six years as Global Head of Talent Development for Salesforce, she has overseen the employee and leadership development of a workforce of 11,000 to over 45,000 employees today. Introducing and building a talent function for scale and with deep purpose has been her life’s work.
Angela is a certified professional coach and has lived and worked in Europe and the US. Her purpose is to help create a better workplace for her daughter’s generation.
“Leadership is an artistic enterprise, creating balance between structure, improvisation, and imagination. The end result is value creation, and to get there leaders must navigate the needs and wants of many stakeholders. The key is for leaders to understand, fundamentally, what kind of value they are creating. What is their intention? From that place of clarity and groundedness, the leader can flourish and make art that has true value.”
Ray is an executive coach, creative entrepreneur, musician, builder, designer, and inventor. He works with entrepreneurs, leaders, and teams who want to make an impact in their companies and in their world.
Ray has spent his career at the intersection of leadership, creativity, and technology. He has had a focus on bootstrapping and lightweight, fast-growing business units. Ray was the CEO and co-founder of an award-winning company concentrated on articulating the voice of brands using music and sound. During that time he worked with diverse clients including Apple, Google, Nike, Pepsi, and many other Fortune 100 brands.
Ray is passionate about corporate culture development and high-performance team management. He also spends a part of his time coaching emerging artists and recent graduates.
“There is much more space within life than we suspect but it’s often hard to access given all our inside and outside noise. This inner ground is, however, the tender territory where we can listen deeply to ourselves and rediscover our innate ability to fulfill what we most yearn for – our life most worth leading. Then the job is getting there.”
Marty guides clients to access their inner resources of awareness, creativity, and confidence so that they become committed to leading from their authentic center. He draws on a rich and varied experience as a business and social entrepreneur, CEO/senior executive, and mindfulness teacher. Marty founded or grew private, nonprofit, and major publicly traded enterprises in diverse sectors including professional services, sustainable design and technologies, environmental performance, retail, and higher education.
Marty speaks, teaches, and consults widely in North America and internationally. He’s served on numerous Boards including an Advisory Board at the Harvard Graduate School of Design, Dalhousie University’s MBA Advisory Board, and as Chair of the Authentic Leadership in Action Institute, Naropa University and the Nova Scotia Round Table on Environment and Sustainable Prosperity. He was selected as a member of the Canada Clean 50, outstanding contributors to sustainable development and clean capitalism. A graduate of ICF Accredited Newfield Coach Training Program, Marty’s career demonstrates that shifts, change, successes, and setbacks are worthy threads in the tapestry of rewarding lives.
“It’s from our vulnerability and awareness that we become the leaders life asks us to be. When we face those challenges with our eyes open, magic happens.”
Jamie champions ideas worth doing and the people behind them. She helps leaders find what they need and develop the persistence to get there.
As a previous executive and co-founder, Jamie is attuned to the challenges faced by her clients. Having operated in environments that demand creative excellence, she brings creativity and practicality into her work as a coach and facilitator.
Jamie is a trained Co-Active coach. Her work stems from an 18-year career in both the for-profit and non-profit sectors, focusing on communication, strategy, creativity, and human development. Her clients included The United Nations, TED, LEGO, Nike, and Google.
Jamie was born in Vancouver, Canada into a Korean and Japanese household. She has lived around the world, speaks four languages and is fortunate to draw from many cultural experiences.