A private room for women ready to claim their influence.
The Penthouse
Because the higher you climb, the fewer places there are where you can think out loud.
Welcome to top floor discussions about life and leadership. This is your invitation to join this executive mastermind curated by Jenny Mitchell, Executive Coach, Underdog Leadership Podcast Host and Professional Fundraiser.
A private room for women ready to claim their influence.
The Penthouse
Because the higher you climb, the fewer places there are where you can think out loud.
You’ve done the work to get here. You’re leading, making decisions, and carrying real responsibility.
And you’re doing most of it alone.
Because something shifts at this level: Your team looks to you for answers. Your peers aren’t really peers anymore. And the people above you are either limited or gone entirely. There are fewer places where you can be candid about what you’re actually thinking.
So the conversations change. You filter more. You hold things longer. You work through decisions on your own because there isn’t an obvious place to take them. Over time, that isolation starts to cost you: slower decisions, quieter confidence, and more weight than you need to be carrying alone.
This is the Gap that The Penthouse was Built For
The Penthouse is a small, private group of women who understand the seat you’re in—because they’re in it too.
It’s not a networking space or a program to move through. It’s a consistent, trusted room where you can think out loud with people who operate at the same level of complexity and responsibility. A place to bring what’s real—and not have to translate it.
What actually happens here
We’re a small, carefully curated group that meets regularly. Private, consistent conversations designed to build trust over time.
We talk about the things that don’t have clean answers.
The decisions that sit with you longer than they should. The dynamics you can’t name inside your own organization. The moments where you’re not sure if it’s a people issue, a strategy issue, or something in between.
Instead of carrying everything alone, you work it through in conversation with other leaders who understand the nuance and stakes.
There’s no posturing and no generic advice. Just thoughtful, honest dialogue that helps you see more clearly and move forward with confidence.
What changes?
The weight you’ve been carrying starts to shift — because you’re no longer holding it on your own.
You start making decisions more cleanly. You trust your thinking instead of circling it. You navigate complexity with more perspective and less internal noise.
This isn’t about becoming a different kind of leader. It’s about becoming more grounded in the one you already are.
You heard it here...
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Why did you join the Penthouse?
I joined the Penthouse because Jenny’s coaching style really aligns with my own professional style. I value thoughtful leadership, strategic thinking, and having space for meaningful reflection, and Jenny creates that in a way that feels both supportive and practical. As an Executive Director, there are often complex decisions to navigate, and I was looking for a space that would support both my professional growth and leadership development in a meaningful way. I also really appreciated the opportunity to connect with leaders from different industries—hearing a range of perspectives challenged my thinking and brought forward ideas and insights I could apply directly within my own organization.
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What is different about the Penthouse from other trainings that you’ve taken?
A combination of practical strategy, thoughtful reflection, and genuine community. Many trainings offer information, but the Penthouse creates space to apply that learning directly to real challenges. The conversations are honest, insightful, and deeply relevant. I’ve appreciated being surrounded by other leaders who bring different perspectives while also understanding the demands of leading an organization.
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What would you say to someone who is contemplating joining the Penthouse?
If you’re looking for a leadership experience that is thoughtful, practical, and genuinely supportive, the Penthouse is incredibly worthwhile. It offers a rare combination of strategy and community, and I’ve come away with both tangible tools and a stronger sense of confidence in my role. It’s been a valuable investment in both my work and my development as a leader.
The Investment
The Penthouse is a year-long commitment to how you lead. The investment reflects the depth of access, support, and conversation inside the room.
You can join in the way that fits how you plan your professional development:
Pay in full
$6,000 for 12 months
Monthly
$500 per month for 12 months
Many participants use professional development or leadership budgets to support their participation.
If this feels like the room you’ve been missing, the next step is a short conversation.
Ready to expand beyond your current comfort zone?
This is for women in senior leadership roles who are already operating at a high level but don’t currently have a space that matches the level of thinking they’re required to do.
You don’t need more information. You need a better room.
Jenny Mitchell
A Note From Jenny…
I started The Penthouse after seeing how many brilliant, capable women were leading at a high level—and carrying more than they needed to.
They didn’t need more training. They needed a place to think. A place to be honest. A place to be in the room with people who truly understood. Shoulders down. Come as you are”
About your coach and mentor.
Jenny Mitchell works with women in senior leadership who are stepping into the complexity of having more visibility, influence, and power — and want to stay human while they do it.
She’s the founder of Chavender, where she partners with executive directors, CEOs, and senior leaders across Canada and the U.S. Her work focuses on helping leaders think more clearly, navigate complexity, and lead with confidence in high-stakes environments.
Jenny has worked with hundreds of leaders and boards across sectors including healthcare, education, arts and culture, and international development.
Her clients are often responsible for major decisions, teams, and funding—and need a space to process that level of responsibility well.
