Discover the support you’ve been waiting for.

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

Know you're not alone. Join the conversation.



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 peer group 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 better with a growth mindset: Leading effectively in a modern organization requires the ability to adapt to anything. Attending 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. Taking time out of a busy schedule to step back, be introspective, and work on your own personal and professional growth is difficult. 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 for the life-giving but difficult work of introspection. And doing so will get you the clarity of 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 support and learnings 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 $595 per month, with an initial one-year commitment. 

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.




Help us get to know you by sharing a bit about your role, your company, the challenges and opportunities you’re facing, and the kind of support you’re looking for. Get started with your application now


Once you complete your application, you’ll be prompted to sign up for a half-hour interview with a member of Reboot’s Circle team. The interview gives us a chance to get to know you better so we can best place you in a group of peers. We’ll also answer any questions you have about the Circles process.

Orientation / In Person Kickoff

Every Circles participant attends an Orientation or an In Person Kickoff where we cover core skills and structures that will set you up for an impactful experience with your group. Circles Orientation consists of two 90-minute virtual sessions (held via Zoom video conference), spaced two weeks apart. Circles Orientations are run every month, so it’s always a good time to jump in. In Person Kickoffs are spaced throughout the year for Seasonally Launched Groups. See below for more information.

Start Meeting with Your Circle

Following the application and interview process, you’ll be invited to join a group of hand-selected peers, led by a Reboot Facilitator.

Meet the Facilitators.

All groups meet virtually (via video conference), twice a month, for 90 minutes each meeting. Some groups (for specific leadership roles) begin with in-person kick-offs. Check out our upcoming in-person launch schedule below.




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

    Jerry Colonna

    Jerry Colonna

Are you a VC interested in sponsoring a Circle for your Portfolio?
Learn more about how you can work with Reboot to support your leaders.

Portfolio Circles


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 one-on-one coaching provide different value emphases:

Circles1:1 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. Some groups are formed around a common functional role, but many of our groups are cross functional. In other words, if you don’t see your specific role or job title reflected on this page, don’t fear! We can find a spot for you. Groups are balanced so that a range of perspectives are brought to each session, allowing for different ways of problem solving to emerge. You’ll have a chance to see anonymized biographies of potential participants before you officially join a group.

How much does it cost to become a member?
Circles Membership is $595 per month. The first month’s payment secures your spot in Orientation sessions. Additional monthly charges won’t begin until you are placed in your Circle. In person kickoffs require an additional cost of $595 (any travel and accommodations are not included in this cost)

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 to 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 realize, however, that scheduling conflicts can happen. If you miss more than four sessions over the course of a year, 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 love in-person gatherings, and some of our groups begin with in-person kick-offs. Also, many of our Circles have chosen to self-organize their own informal meetups, which we love.

I still have more questions, can I speak to someone?
Yes! Just email us at and someone will be happy to answer your questions.

  • “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