Be the leader you want to be.

Reboot Circles are an effective and unique way for VC firms to provide ongoing support and professional development for CEOs and leaders inside their portfolio companies. Circles are curated peer learning groups that cultivate growth from the inside out. Led by a skilled Reboot coach, six Circles Members in similar roles and stages in their journeys come together to support each other’s personal and professional development.

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Portfolio Circles


  • Support your portfolio companies: Investors are always looking for ways to support portfolio CEOs and their Executive Teams. Reboot Circles are a unique form of support where Circles Members get to dive deep into their own challenges while learning from their peers, all guided by a Reboot-trained coach skilled at keeping the circles focused and on point.
  • Build community across your portfolio: Being a CEO or leader is lonely and difficult. As a company grows, the loneliness often increases. One of the best ways you can support your portfolio companies is bringing them together with others to support one another and strengthen the community within your portfolio.
  • High impact at a low cost: We do the heavy lifting for you: Once you work with us to invite CEOs and leaders from your portfolio, we take it from there.
  • Potential increase in ROI: While never guaranteed, studies have shown that CEOs who have professional development as well as peer support are more likely able to ride out the naturally-occurring ups and downs of launching a startup. More effective CEOs and senior teams are more likely to successfully launch business, increasing the effective rate of return across a portfolio.


  • Feel more in control and less stressed about work: Struggles seem bigger and more overwhelming when we are isolated from others who can help. Circles Members feel better and more in control with a go-to group of peers they can trust to help them problem-solve and be there when the going gets tough.
  • Lead better with a growth mindset: Leading effectively in a modern organization requires being able 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 growth by tapping into the variety of experiences and perspectives of others. As Circles Members update and revise their mental models, they’ll gain more influence and impact.
  • 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. A Circle is protected time in a CEO’s or leader’s schedule to work on self. We’ll hold them accountable for the life-giving but difficult work of introspection. And doing so will get them the clarity of what it means to live in alignment with their deepest values. We call this inside-out leadership development.

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


Reboot Circles create a container of safety, inquiry, and accountability from which the authentic, resilient leader within 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.

Reboot partners with your firm to identify the CEOs or population(s) of leaders you’d like to support (e.g. Head of Engineering, Head of People, etc.). You confidentially help us understand what’s important to you at a high level, and then we’ll take care of curating the group with your goals in mind (which typically involves a written application and a short phone interview for each prospective participant).

Here’s what happens once we’ve curated a group:

  • Groups launch with a half or full-day in-person kickoff session (which can be hosted at one of Reboot’s offices in SF, NYC, or Boulder). These kickoffs accelerate the cohesion within the group.
  • After the kickoff, groups meet virtually (via video conference), twice a month, for 90 minutes each session.
  • Reboot will conduct at least one feedback session both with our survey and with phone interviews and share that feedback with Firm.


  • "My Circles experience has fundamentally shifted the way I work with my team. It had better equipped me to coach both myself and my leadership team. We've been able to shift our focus from solving so many tactical problems, to creating structure in place with the right culture that encourages the team to self identify and be empowered to solve problems."

    Sean Knapp

    CEO, Ascend.IO

Ready to learn more?


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

    Jerry Colonna

    Jerry Colonna

Interested in running a peer group in your own organization? Check out our definitive guide for building safe spaces for peer support groups.

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How do Circles compare to 1:1 coaching?
While not mutually exclusive, Circles and one-on-one 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 from three different perspectives aslistener, 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.

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