The Strategy Boutique
About Our Founder
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Jessie Sleep
Founder & Managing Director, The Strategy Boutique
Jess is a strategic leader, community builder, and working mother of three with over a decade of experience at the intersection of corporate governance and community impact.
As a CEO, Managing Director and Strategic Partner of multiple community-focused organisations, her work has spanned economic development, regional investment, health and wellbeing, and social empowerment. These weren’t just corporate roles — they were deeply personal commitments to the region she called home, and others she holds as close family.
Throughout her leadership career, Jess has carried the dual weight of high-level responsibility and heartfelt service. She knows what it means to deliver on performance and funding metrics — while also holding space for the people, cultures, and futures those numbers represent. When the work is personal, it doesn’t stop at the office door. And for her, it never has.
After years of leading from the front, she chose to pivot — not because she couldn’t keep going, but because she wanted to create impact in a new way. With a newborn in arms and a renewed sense of purpose, she has stepped into a slower, more aligned chapter.
Now, through The Strategy Boutique, she supports leaders, changemakers, and organisations to build capacity, clarity, and systems that serve both purpose and people. Her approach blends strategic rigour with emotional intelligence, and honours the truth that great leadership starts within.
Jess is also the heart behind 'That Aligned Life' and The Village Hub, two offerings designed to nurture energy, intention, and community in the lives of those doing the hard (and often invisible) work.
While she brings over a decade of high-level experience, Jess leads with grounded realness. She lives her values, speaks her truth, and reminds us that doing meaningful work doesn’t require perfection — just alignment.
“Not perfect, just real.”
About TSB
Hi!
I’m Jess, founder of TSB.
I’ve spent my career working across communities, boardrooms, and everything in between. From regional, rural, and remote Australia to government offices and corporate headquarters, I’ve had the privilege of brokering relationships between community, government, corporate, and philanthropy — and with that, I’ve seen the drivers of change as well as the blockages that hold it back.
What I noticed was simple but powerful:
Too often, external parties come in, deliver, and leave.
They apply their own frameworks, sometimes without fully understanding the context. And in doing so, they create reliance instead of resilience.
That’s not what I stand for.
The Strategy Boutique was created because we believe capacity-building isn’t a “nice to have” — it’s the only way we grow strong communities, organisations, and leaders.
Through our four core offerings, we focus on equipping people with the tools, strategies, programs and aligned systems they need to thrive. Whether that’s in leadership development, diversity and inclusion, partnerships, or personal alignment, the goal is always the same:
"every engagement should leave people stronger, more capable, and more confident than when we arrived"
This isn’t about parachuting in with a “solution” that doesn’t fit.
It’s about walking alongside, understanding unique contexts, and helping develop the capacity to keep moving forward long after we’re gone.
Our Philosophy
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Build capacity, not dependency.
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Focus on teaching, not just telling.
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Embed context so solutions are real and sustainable.
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Create ownership and leadership from within.
Whether we're working with a corporate leadership team, a small business, not for profit organisation, or a grassroots community, my mission is the same:
To walk alongside, not above, and to leave behind capacity that lasts.
Why “Not Perfect, Just Real”?
Because leadership, culture, and growth aren’t about chasing perfection — they’re about authenticity. At TSB, we don’t believe in one-size-fits-all answers or polished templates swapped out with a new name. We believe in listening, co-designing, and creating strategies that are honest, grounded, and real.
Want to know more? Explore our offerings or connect with us on Linked in or Instagram on the icons below.