Leadership Groups for You and Your Team

Reboot Circles are facilitated peer coaching groups for vital leadership roles in your company. Grow as a leader from the inside out. Gain clarity on your leadership style, understand what drives you and what holds you back, develop skills to lead more effectively, and help others in your group do the same.

Know you're not alone. Join the conversation.



  • “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 peer group provides me with an excellent forum to open up and overcome some of my biggest challenges as a leader.“

    Bobby Brannigan

    Bobby Brannigan

    Founder and CEO Mercato – Reboot Circle Member


Does this sound familiar?

You are leading a growing startup—originally, you set out to change the world…But now, you’re just trying to keep your head above water. There’s the long hours. Constant demands. Never­-ending­ and unforgiving­ “To Do” ­lists.

Not to mention the personal toll a startup can take: Pressure from your board. From your co-founders. From your employees. From your significant other.

It can be a stressful and lonely journey. You might feel embarrassed or guilty for even feeling this way. You’re “living the dream,” right? Isn’t this what you signed up for?

Or maybe you’re thinking, “If we can just solve this one problem…” or “Make it to this next round of funding…” then “it’ll be smooth sailing!” The truth is, the challenges and pressures never go away. They simply change.

But that doesn’t mean you have to settle for sleepless nights, knots in your stomach and feeling like you’re doing this all on your own.

There’s a way you can continue to pursue your dream, but live a more balanced and stress-free life. There’s a way you can solve any business or life issue… and it doesn’t involve working longer hours or sacrificing another meaningful area of your life.

What if you had a place and a group who would always be there to support you in solving your greatest business challenges? What if you had a group you knew you could always count on?

More specifically, what if you had a team of five other smart and courageous start-up founders… people who were going through the exact same journey you are right now…And what if they were willing to help you think through your stickiest strategy problems? Or your most vexing challenges with your co-founder? Or simply hear you out as you think through a new hire you have to make?

Well, that’s precisely what we’ve created with Reboot Circles – Coach-led groups for founders and high growth startup executives.

Reboot Circles are Reboot-vetted, professionally facilitated groups designed to help you become the leader you were meant to be.


CEO Group

Applications due by April 15, 2017

CEOs in Transition

Applications due by March 27, 2017

Women Startup Leaders

Applications due by April 1, 2017

Head of Product Group

Applications due by April 15, 2017

CTO/VP/Head of Engineering Group

Applications due by April 15, 2017

Head of People Ops Group

Applications due by April 15, 2017

Head of Marketing (CMO/VP of Marketing) Group

Applications due by April 15, 2017


Groups meet virtually (video conference), twice a month, for 1.5 hours each meeting. Group members commit to being together for 6 months. Group sessions involve a mix of potent exercises, elegant conversation structures, and time to process pressing issues and concerns. The facilitator holds the space, allowing for powerful insights and discoveries to emerge in the interactions.

What makes Circles distinct from other local leadership networks or meetups is the active role Reboot plays in crafting the group experience. That means the unique aim of our groups is to help you:

  • Become a more resilient, successful leader
  • Use the existential challenges that arise from your own inner work, moving more fully into your adult human self
  • Ease the pain of the vagaries of everyday life


Just to be clear–Reboot Circles are not about self-indulgent navel-gazing. Stepping into this work has implications beyond your own personal transformation. During the peer coaching process, you’ll gain clarity on who you are as a leader, develop skills to lead more effectively, and help others in your group do the same.

Specifically, Reboot Circles give you:


A problem solving community
You’ll always have a place to go when you need to process a hard problem. Get connection and support from a close-knit group of qualified peers who can identify with each other’s opportunities and challenges.


Enhanced leadership
You’ll hone your capacity for sustaining open conversations that leverage the collective wisdom of a group–the very same kind of conversations that can support innovation and creativity in your organizations. Think “leadership practice field.”


Tools for radical self inquiry
Emerge with a clearer sense of what drives and inspires you, how to make the most of your unique leadership gifts, and how to face the internal and external challenges holding you back.


Trusted guides
Reboot brings together a team of coaches with wide-ranging experience and expertise. You’ll have access to their wisdom through exclusive Reboot content.

Ready to Become a Reboot Circle Member?

Apply for Membership

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

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

    Jerry Colonna

    Jerry Colonna


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 and safe space within the group, so we need everyone to be committed.

What else do I get in addition to monthly group meetings?
Members get access to exclusive Reboot content, as well as preferred access to events like bootcamps and workshops.

Who arranges the meetings and helps facilitate them?
All Reboot Peer Coaching Groups 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 peer group to have the highest value for all of the participants, we ask that you make attendance a priority. However, we do realize that scheduling conflicts can and will happen from time to time. We ask participants to commit to attending at least 20 out of the 24 group meetings for the year. If you miss more than four sessions, it’s possible you could be asked to leave the group.

What if I need to quit?
We know that things come up, so if you need to leave the group we’ll work with you to remove any remaining group obligations. You will not be obligated to pay the remaining monthly fee of your commitment.

How are meetings structured?
Our groups meet virtually and adhere to the Circles of Trust principles. Each meeting will have a guiding theme and/or exercise, and there will be time for reflection and sharing over the course of our time together. Your facilitator will guide the conversation to allow for what needs to emerge and to keep the conversation focused when needed.

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-person peer coaching group options soon.

How do groups come together?
Groups are made up of six people and are organized based on factors such as location, availability, company size and prior relationships. A Peer Coaching Group is a year long facilitated small group process, requiring the full commitment of all six participants. There are limited spaces available, and we carefully match each group based on the individual participants, honoring any previously shared experiences.

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