From CEO to Enabler: The Leadership Philosophy Behind Empowering Others

Send us Fan MailIn 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-ZipserFollow us on Instagram, TikTok and YouTube.