Leadership Coaching
Designing the leader — and future — you want to grow into.
Leadership coaching is a core part of Groundcover’s work, offered directly by founder Jessica O’Dowd.
A Note from Jessica
As a Certified Lightyear Leadership Coach, I work with leaders at all levels and career stages who are navigating transition, questioning their next steps, or feeling constrained by patterns that seem to repeat themselves.
Coaching is where this work becomes most personal. I’m passionate about supporting leaders to move beyond inherited expectations and consciously design what comes next.
Clients often arrive feeling overwhelmed or at a crossroads. What they share is a desire to lead, and live, with greater intention, choice, and purpose.
The good news is that leadership is not something you grow into by accident. It’s something you choose, and practice, over time.
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Coaching is a strong fit if you are:
In a period of transition or redefinition
Stepping into expanded leadership responsibility
An emerging or senior leader who feels constrained or held back from your full potential
Wanting to create a future that feels purposeful, not accidental
I work with leaders across all levels and sectors who are ready to think more expansively about who they are becoming. My clients share a common desire: to lead, and live, with greater intention, compassion, and agency.
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The Lightyear Leadership framework is a future-focused approach that helps leaders step beyond inherited expectations and consciously design what comes next.
Together, we focus on:
Getting clear on what you want, and what you no longer want
Identifying and moving beyond limiting beliefs
Expanding your sense of choice in complex situations
Designing a compelling 10-year vision for your life and leadership
Translating that vision into meaningful goals and personal commitments
This work is transformational, but it is also practical and structured — designed to support real decisions and sustained change.
What Clients Experience
Clients often describe their experience as:
Transformative and future-opening
A shift from overwhelm to possibility
A renewed sense of choice and agency
Greater confidence in how they show up as leaders
The ability to lead with more clarity and compassion
This work helps people “unlock their future” — not because it changes who they are, but because it expands how they see themselves and what they believe is possible. Together, we create momentum by clarifying what matters most and crafting the tools to go after it.
What People Are Saying
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I didn’t need to fix anything — I needed a broader perspective. This work helped me make choices that created more space in my life.
— Rosie Nathoo, Director, Professional Services
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As I stepped into a rapidly evolving leadership role, I found myself unsure whether being a leader was something I could — or even wanted to — do. Working with Jess helped me find greater stability and confidence, while holding space for my development both in and beyond work. Her coaching is compassionate, grounded, and gently challenging in exactly the right way.
— Kate Bell, Marketing & Communications Manager
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Working with Jess was empowering and honestly transformative. She creates a space that feels safe and focused, where you can be honest about what’s really going on without feeling judged or rushed. The biggest shift for me was in how I relate to my leadership. I became more intentional and less reactive, with more self-awareness and confidence. Instead of seeing challenges as proof of inadequacy, I began to see them as signals for growth.
— Renee Williams, Program Manager
How Coaching Engagements Work
Coaching engagements are intentionally limited to allow for depth, presence, and meaningful transformation. Packages are tailored to each client and may stand alone or complement organizational work. I create space for a limited number of engagements each year.
Sessions balance future-focused exploration with practical reflection on real decisions, relationships, and leadership challenges you’re facing now.