Be the leader you want to be.

Reboot Circles are carefully curated peer learning groups that cultivate growth from the inside out. Led by a experienced Reboot coach, you and 5 of your peers come together to support each other’s personal and professional development.

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1. Feel more in control and less stressed – Our struggles always seem bigger and more overwhelming when we’re isolated from others who can help. You’ll feel better and more in control with a go-to group of peers you can trust to help you problem solve and be there when the going gets tough. You don’t have to do this alone.

2. Lead smarter with a growth mindset – Leading effectively in a modern organization requires being able to adapt to anything. Business school and reading the best blogs can’t build resilience–resilience comes as you apply a learning mindset to the highs and lows of life experience. Learning together with a group maximizes your growth by tapping into the diverse experiences and perspectives of other leaders. As you update and revise your mental models, you’ll gain more influence and impact as a leader. You don’t have to be held back by your blind spots.

3. Become the best version of you – Being a better leader starts with being a better human. As a busy leader making time to step back, be introspective, and work on your own personal and professional growth is hard. It’s the first thing to get papered over when your calendar fills up. Your Circle is protected time in your schedule to work on you. We’ll hold you accountable to doing the life-giving (but difficult) work of introspection, and you’ll get clarity on what it means to live in alignment with your deepest values. We call this inside-out leadership development . You don’t have to experience work and life as a passive observer.

4. Join the Family – Reboot brings together a team of coaches with wide-ranging experience and expertise. You’ll have access to their wisdom through exclusive Reboot content.

“Becoming a leader is synonymous with becoming yourself. It is precisely that simple and also that difficult.” – Warren Bennis

Still have questions? See our FAQ


Reboot Circles create a container of safety, inquiry and accountability from which the authentic, resilient leader within you can emerge. Group sessions involve a mix of coaching exercises, guided journaling, facilitated group exploration and time to process pressing issues and concerns. The facilitator holds the space and provides loving provocation, allowing for powerful insights and discoveries to emerge.

Groups meet virtually (via video conference), twice a month, for 90 minutes each meeting. Membership is $1,500 per quarter with a twelve-month initial time commitment ($6,000 for 24 professionally facilitated sessions), with the intention of creating lifelong, supportive relationships among group members. Groups are launched quarterly, and membership is offered to the first six qualified and curated members. The intention of Reboot Circles is to facilitate the creation of lifelong, supportive relationships among group members. Some of our Circles have chosen to keep meeting for multiple years! We’ve created the arc of an experience over the first year to help participants grow individually and form a strong learning community.


  • Matt Hoffman

    Matt Hoffman

    VP of People, Digital Ocean

  • Jay Levy

    Jay Levy

    Co-founder and partner Zelkova Ventures

  • Bobby Brannigan

    Bobby Brannigan

    CEO of Mercato, Reboot Circle Member


CEO Group

Applications due by June 15, 2017

Head of People Ops Group

Applications due by June 15, 2017

Head of Marketing (CMO/VP of Marketing) Group

Applications due by June 16, 2017

Co-Founder (non-CEO) Group

Applications due by June 16, 2017

Head of Product Group

Applications due by June 16, 2017

CTO/VP/Head of Engineering Group

Applications due by June 16, 2017

CEOs in Transition

Applications due by August 31, 2017

Women Startup Leaders

Applications due by August 31, 2017

  • “The hardest part of scaling people is learning to lead yourself.”

    Jerry Colonna

    Jerry Colonna


How do Circles compare to 1:1 coaching?
Circles and Coaching are not mutually exclusive, and in fact many members pursue both, however Circles and 1:1 coaching provide different value emphases:

Circles 1:1 Coaching
Connect with a group of leaders who are experiencing the same set of challenges, guided by a skilled facilitator. Connect with a with a skilled advocate who’s in your corner at all times.
Learn by taking turns as listener, helper, and focus person. Take a deep dive into what’s present for you, with focused support.
Steady drumbeat of exploration to make sure you have time to work on you with a community to share in your journey. Space to tackle big chunks of personal and professional development work.

Who will be in my group?
Group participants are considered and selected based on role, company size, revenue and/or funding model and desire to learn more about themselves and how they are showing up in the world and in their roles. Groups are balanced so that a range of perspectives are brought to each session, allowing for different ways of problem solving to emerge. You will have a chance to see anonymized bios of potential participants before you officially join a group.

How much does it cost to become a member?
Membership is $500 a month with a 6 month commitment. It takes time to develop the trust andsafe space within the group, so we need everyone to be committed.

What else do I get in addition to monthly group meetings?
Members get to connect with a talented group of peers they trust who can advise them on all aspects of their roles including tools and tactics for tackling the day to day challenges. Members also get access to exclusive Reboot content, as well as preferred access to events like bootcamp sand workshops.

Who arranges the meetings and helps facilitate them?
All Reboot Circles are arranged and facilitated by our professionally trained facilitators. Our facilitators receive ongoing support from Reboot as well as ongoing professional development training.

What happens if I don’t have the time to make it every meeting?
Because your full commitment is necessary for the group to have the highest value for all participants, we ask that you make attendance a priority. We do realize, however, that scheduling conflicts can happen. If you miss more than four sessions, you may be asked to leave the group.

Do virtual meetings work?
Yes. Meeting virtually ensures flexibility and ease of attendance for the bi-monthly meetings,allowing us to prioritize consistency, quality facilitation, and careful group creation. That said,we realize that in-person meetings can be incredibly powerful, and we will be offering in-personpeer coaching group options soon.

I still have more questions, can I speak to someone?
Yes! Just emails us at and someone will be happy to hop on the phone withyou or answer your questions via email.

Ready to Become a Reboot Circle Member?

Apply for Membership

A Reboot Facilitator will contact you within 48 hours to determine next steps.

  • “All these people can’t be crushing it,” says Jerry Colonna, adviser to executives from startups like Etsy, and SoundCloud. “It’s bullshit. It’s spin.”

    Reboot’s Jerry Colonna in Fortune article

    Reboot’s Jerry Colonna in Fortune article

  • “As an entrepreneur constantly trying to grow and bust out of my comfort zone, my Reboot Circle provides me with an excellent forum to open up and overcome some of my biggest challenges as a leader.”

    Bobby Brannigan

    Bobby Brannigan

    CEO of Mercato, Reboot Circle Member

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