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From CEO to Enabler: The Leadership Philosophy Behind Empowering Others
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In this episode of The Tech Trajectory Podcast, host Kavita Kerwar sits down with Roby Sharon-Zipser, Co-Founder and CEO of hipages Group, to explore how leadership evolves as a business scales—from garage startup to ASX-listed tech company. Roby unpacks what it takes to move from being a hands-on founder to an enabler of innovation, how to build a culture of strategic execution, and why staying curious about technology—especially large language models—is key to future growth.
1. Evolving from founder to enabler
[04:42] How Roby’s leadership style shifted from micromanagement to team empowerment as hipages scaled.
[06:32] What it means to step back and elevate your team with trust, clarity, and accountability.
[07:24] The importance of letting go of low-value tasks and building out an executive team.
2. Building purpose into strategy
[10:04] How hipages keeps its dual customer base—tradies and homeowners—at the centre of decision-making.
[11:38] Roby breaks down how AI and cross-functional teams are improving customer experience across the board.
[14:22] End-to-end customer journeys: why true innovation requires integration beyond the top of the funnel.
3. Leveraging large language models (LLMs)
[11:48] Roby’s first reaction to LLMs: from confusion to realising their transformative potential.
[15:37] The risks and rewards of LLMs—why hallucinations, security, and accuracy matter.
[17:52] How hipages is using AI to streamline internal processes and customer interactions.
4. Scoring innovation and strategic execution
[19:47] Scaling the tech team and building a product-led culture from the ground up.
[22:11] Internal scoring frameworks: how Roby weighs commercial value, customer impact, and long-term ROI.
[24:57] Why not every idea has a direct revenue line—but some drive lasting retention and experience gains.
5. Advice to his younger self
[26:09] Network early, network often—the compounding power of shared founder experience.
[28:56] Favourite books, podcasts, and frameworks that shaped Roby’s thinking, including The Hard Thing About Hard Things and Seven Powers.
[31:36] Why listening, learning, and structured strategy execution are key to scale.
6. Founder reflections and what’s next
[32:53] What Roby loves most about his job—from company-wide presentations to robust debates.
[34:59] His least favourite part? The admin-heavy side of performance reviews.
[38:48] The hardest part of scaling: capital management, making tough calls, and staying focused on long-term survival.
[41:36] What’s next for hipages.
Where to find Roby Sharon-Zipser
- Website: hipages.com.au
- LinkedIn: Roby Sharon-Zipser
6 episodes
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