Startup Cafe: The Empowered Workforce Shift: You Have More Power In It Than You Think
The backdrop is moving fast
Entire job functions are being rewritten by AI overnight. Seed capital is slower, smaller, and harder to get than it's been in a decade. Founders are being asked to do far more with less. And the speed dial on everything has been turned up to the max.
Nobody handed anyone a map for this.
There's a lot of noise right now telling us what's dying, and much less about what's actually being born.
The way people work inside companies is being rebuilt in real time: how leaders need to lead in an AI world, a growing fractional workforce, and what career security actually looks like.
This conversation is about how you get on the right side of this change. Whether you're the one building the company or the one working inside it.
With 40 years of recruitment experience between them, Matt Bennett and Holly Gottlieb sit on two sides of this workforce shift. Matt works inside leadership teams on how founders and leaders hand over decisions and grow people who can carry them. Holly builds the teams themselves, placing senior fractional operators into growing companies, and helping people navigate this career shift.
What we're getting into
How founders stop being the bottle neck and move from operator to strategist.
What people-centric AI leadership actually looks like
Why the Fractional workforce is growing and how to leverage it
How the empowered founder isn’t waiting for someone to ‘come save them’
Who this is for
Founders and early operators in growth mode, anyone working inside a company, or between companies, who are trying to navigate this rapid workforce shift.
What you'll walk away with
A framework for structuring work in the new economy, fractional vs. full-time, leveraging AI tools in an effective way, whether you're hiring or being hired
Tools for founders in leading an empowered workforce, and how to stop being the bottleneck
A concrete view of how senior people are actually finding work right now, and how to build income that isn't dependent on one employer
Agenda
8:45 - 9:30 am • Coffee and Socialize
9:30- 10:30 am • Conversation in the Clubhouse, Brief Q&A
11:00 am • Space closes to public
September 9, 2026
SPEAKERS
Matt Bennett : Executive coach working with founders and leadership teams on decision-making, delegation, and the shift from operator to strategist.
Matt's work centres on a pattern he sees in nearly every company he enters: the growth ceiling is usually the founder's willingness to let other people decide.
Holly Gottlieb : Founder of The Whole Collective, Holly has spent the last 14 years placing leaders and operators for some of the fastest-growing venture-backed companies across the US and Europe.
She now places fractional talent into mission-driven businesses, and is obsessed with building a life of purpose and creativity, and how we find a life of happiness and fulfilment whilst still paying the bills - a journey she writes about in her Substack.
🔗 LINKEDIN 🔗 WEBSITE 🔗 SUBSTACK
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