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A confidential space for leaders tired of carrying it all alone.

A private, facilitated support group built for founders and CEOs who crave connection, clarity, and grounded advice (without the pressure to “hold it all together”).

Kick burnout to the curb.

Most leaders don’t burn out because the work is too hard. They burn out because they have nowhere to process it. 

This group is designed for CEOs who:

  • Feel isolated in their role or rarely have peers to talk to

  • Want to unlock clearer thinking and steadier decision-making

  • Are navigating growth, layoffs, pivots, or team challenges

  • Crave honest conversations with people who get it

  • Are tired of being the emotional shock absorber for their company

 

If you’ve ever said, “I can’t talk to my team about this,” you’re in the right place.

Find your community.
Real support. Zero pretense. 

What you get

  • Monthly facilitated small-group sessions (intimate, confidential, high-trust)

  • A space to process big decisions and tricky team dynamics

  • Guidance from an experienced operator who understands the emotional load of leadership

  • Connection with peers who understand leading through uncertainty

  • Tools, scripts, and frameworks to use immediately with your team

  • Space to think, exhale, and reset

How it works

  • Cohort Size: 6–8 CEOs like you

  • Format: Virtual, 60-minute monthly sessions

  • Full Confidentiality: what’s shared here, stays here (NDAs available)

  • Optional 1:1 coaching between sessions

  • Commitment: 3-month minimum enrollment

What You Get

After three short sessions, your team will walk away with:

How It Works

All sessions are remote-friendly and can be completed in as little as one week. 

“If you’re considering working with Robin, do it! You won’t just get a great facilitator; you’ll get a true partner who listens deeply, adapts in the moment, and knows how to unlock a team’s potential. You’ll come away with more than ideas and plans — you’ll leave with alignment, energy, and trust.

Carla James
CEO of Solidus Technical Solutions, LLC
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Why It Works

  • Facilitated by someone who has been in your shoes

  • Gets everyone in the room aligned & focused

  • Forces clarity on what matters, and what doesn't. 

  • Saves you hours of time downstream

Invest in yourself

Commitment: $500/mo

Includes:

  • (3) 60-minute virtual group session with 6-8 CEOs (monthly)

  • (3) 30-minute 1:1 executive coaching sessions  

  • Access to communication tools, frameworks & best practices 

*It's critical to build trust & connection within each CEO cohort. To encourage authenticity, continuity, and relationship-building, we require a minimum of 3 months' commitment to join. 

Pack Pricing:

  • Quarter Pack: $1500 ($500/mo) for three sessions

  • Half Pack: $2,800 ($466/mo) for six sessions

  • Annual Pack: $5,400 ($450/mo) for twelve sessions

TRUSTED BY CEOs & EXECUTIVE TEAMS AT
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FAQs

What size company is this for?

I usually work with companies that have between 30-80 employees, but all sizes are welcome. It's never too early (or too late) to think about scale, efficiency, and better ways of working. I specialize in creating fast startup planning services for SaaS companies, B2B, B2C, apps & more. 

Do we need to prep anything beforehand?

Just come with your current goals (if any) and who owns what. I'll take it from there.

Who should attend? 

Teams usually include all c-suite members + relevant department heads (Product, Marketing, Sales, Engineering, Customer Success & Finance). 

Can we customize our planning session?

Absolutely. Each team's needs are different, and my goal is to meet you where you're at, wherever you are (in-person or remote). Together we'll create a startup strategic planning workshop that incorporates pressure-tested goal-setting frameworks. 

Where do we start?

Let's hop on a free, 30-minute call to discuss your needs & goals. This is a no-pressure conversation where we'll chat about the current state of planning. If we're a fit, I share a proposal, you sign, and we're off to the races.

Can we work together if I'm abroad? 

Of course. I work remotely with early-stage tech companies across the U.S., Canada, Europe and beyond. Prefer live, in-person facilitation? Available in Boston, New York, San Francisco, London, Toronto, and more. Contact me to discuss in-person facilitation in your city. 

Meet Your Facilitator

Hi, I'm Robin, professional facilitator, factional COO & operations expert. After 10+ years of building & leading teams for some of the world's most popular apps, products, and marketplaces, I've seen it all (and supported all types of CEOs along the way). My mission with the CEO Support Group is to encourage open, honest conversations that help you solve your biggest problems you can't talk to anyone else about.

Former retention & operations at:

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Ready to stop spinning & start executing?

Located in Boston, MA, available for consultation around the globe.

© 2026 by Happier Office LLC. Email: robin@happieroffice.com

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