SUNDERLAND CEO CIRCLE,
CEOS & Leaders fueled by
purpose & calling
A Private Leadership Mastery Forum for CEOs Committed to Sustainable Growth
The Sunderland CEO Circle is a high-level leadership forum for CEOs who want to develop themselves, strengthen their teams, and scale their organizations with clarity, intention, and accountability.
This is where leadership development, organizational excellence, and sustainable revenue growth converge.
Why This Circle Exists
CEOs cannot see their own blind spots, and they cannot lead effectively in isolation.
The fastest growth happens when leaders have:
A trusted peer group
An experienced facilitator
A structured space to process real challenges
Support interrupting the patterns that limit performance
The Sunderland CEO Circle brings all of this together.
What you get
🌀 Monthly 2.5-Hour CEO Roundtable
A confidential space for real conversations about:
What’s working,
What’s not working,
Strategic decisions,
Team dynamics,
Revenue concerns,
And the mindset patterns that keep leaders stuck.
This is where clarity accelerates and blind spots dissolve.
🧭 Monthly 1:1 Coaching Session (50 minutes)
Deep, customized support so each CEO moves forward with alignment and precision.
🚨 SOS 10-Minute Spot Coaching Calls
Rapid support when urgent decisions, fires, or conflicts emerge.
📚 Tools + Methodologies
We’ll integrate:
The 15 Commitments of Conscious Leadership
(reduce reactivity, increase clarity, improve decision-making)Enneagram + IEQ9
(uncover driving motivations, behavior patterns, and break old cycles)
These tools give CEOs practical ways to lead with more presence, consistency, and impact.
🛡 A True Leadership Community
The Sunderland CEO Circle is built on:
Trust
Authenticity
Responsibility
Impeccability
Creativity
Fun
🌄 Going Deeper Package Upgrade: Annual 2-Day Leadership Retreat
Two (2) 1:1 monthly coaching sessions + Retreat
A reset and renewal experience designed for strategic planning, authentic connection, and transformational growth.
Debra is also available for team coaching and your personal VIP day
This is a place to be real, supported, and challenged — not polished or performative
Common CEO Challenges We Address
CEOs bring issues like:
Scaling and getting out of the weeds
Misaligned or underperforming teams
Revenue inconsistency or pressure
Conflict + miscommunication
Decision fatigue
Not enough time, talent, or resources
PE pressures
Hiring/firing challenges
Burnout
Working in the business instead of on it
No trusted peers to run decisions by
Neglected purpose or vision
Loss of time with family / quality of life
The Circle exists to solve these.
Some Benefits of Participation Include:
A community where you do not need to have all the answers
Support navigating difficult decisions and complex leadership challenges
Fresh insights when stuck or too close to the issue
Perspective from peers who understand the weight of leadership
A confidential space for honest dialogue and vulnerability
Growth through challenge, reflection, and expanded awareness
Leadership development aligned with business and personal evolution
Tools to improve communication, resolve conflict, and reduce drama
Support in building responsible, curious, and aligned teams
Financial, strategic, and legacy-focused conversations
Opportunity for retreat-based integration (where applicable)
Our Commitment:
We are here to make your leadership, your organization, and your life the strongest and most aligned they can be.
When one CEO learns, the entire group rises.
When one person breaks a pattern, everyone grows faster.
This is a place for accelerated evolution.
If you want to grow your business, book an initial 30-minute discovery call with Debra.
What others say about working with Debra:
“We've been working with Debra since the early days of Spinach.io and she's been instrumental to building our team and culture foundations.
The work with Debra, focused on Conscious Leadership, has helped us foster a culture of taking responsibility, openness and connection. Through the work with Debra our team has become better at communicating and collaborating—getting curious about other perspectives, revealing thoughts and working through conflict. It has also helped us optimize for keeping our team in their zone of genius, which has significantly improved outcomes.
The work with Debra around our enneagrams types has helped us both individually and collectively—see our strengths and limiting patterns, and better understand each other's motivations which led to more empathy.
Any team would be fortunate to work with Debra and see the impact her coaching can have. The sky is the limit!”
- Matan Talmi | Co-Founder & CEO, Spinach.io | Nashville, TN
“I was not sure what to expect from our management retreat with Debra, but every member of our senior team was blown away and left eager to continue working with her. She swiftly identified long-standing issues and perceptions that prevented us from working together as an effective team. Using empathy and understanding she gave us several tools we could use to reduce conflict. We're grateful to have discovered someone who can accompany us on the path to becoming more conscious leaders and in the process, reduce the stress and strain that is a byproduct of managing and living an unconscious life.”
- Rob Gordon | CEO & President, Nashville Public Radio | Nashville, TN
“I have been working with Debra one-on-one for a few months now. It’s almost hard to put into words the profound impact our work has had on me as a Leader and as a Person. Debra has a remarkable way of leading conversations to help create self-awareness around the source of behaviors and beliefs.
Through our collaborations, I feel I have begun a transformative journey with a whole new perspective on what makes a great Leader. I am always excited to meet with Debra. Her compassion for people and her passion to spark change and awareness is contagious.
I would recommend Debra to anyone who is looking to go beyond business as usual and make a meaningful impact as a Leader.”
- Howard A. Weiss | President, Esser Hayes Insurance Group | Naperville, IL
About Debra:
Debra Sunderland is an executive coach and leadership facilitator specializing in helping CEOs and their teams create aligned, accountable, high-performance cultures. With decades of experience coaching C-level leaders across industries—including wealth management, engineering, healthcare, marketing, and hospitality—Debra is known for her ability to identify blind spots, strengthen communication, and drive sustainable organizational growth. Her approach integrates Conscious Leadership, the Enneagram (IEQ9), and evidence-based leadership frameworks to support better decision-making and measurable results. Debra has partnered with organizations ranging from Fortune-level companies to fast-growing startups, and her work has been featured on ABC, NBC, Fox, Crain’s Chicago Business, and the Chicago Tribune. She is based in Nashville and works with clients nationwide.