How Janie and Jack’s CIO transformed a legacy tech stack into a scalable retail growth engine
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Published by Noibu | The Ecommerce Toolbox: Expert Perspectives
Guest: Madhav Kondle, CIO of Janie and Jack
Host: Kailin Noivo, Co-Founder at Noibu
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Imagine stepping into a CIO role and discovering that your core systems haven’t been meaningfully updated in half a decade. Your ecommerce platform is outdated. Your POS system traps store associates behind a counter. Your PLM system is old enough to drive. And your business, fresh off major ownership transitions, is accelerating faster than your technology can handle.
That was the reality Madhav Kondle inherited when he joined Janie and Jack.
In this episode of the Ecommerce Toolbox: Expert Perspectives, host Kailin Noivo sits down with Madhav to unpack how he executed one of retail’s most complex digital reinventions: modernizing a fragmented legacy stack, navigating spinouts and acquisitions, and building a technology foundation capable of supporting premium brands.
But this story is much bigger than a systems overhaul. It’s a defining example of how modern CIOs must think - commercially, cross-functionally, and with an unrelenting focus on business impact.
The big idea: Why CIOs must stop thinking like technologists
The most effective CIOs aren’t defined by infrastructure mastery, they’re defined by business fluency.
Madhav’s path from software engineer to enterprise leader gave him a rare advantage: he learned the language of merchandising, marketing, finance, and operations. And that perspective shaped his philosophy: technology only matters if it moves the business.
In an industry where retailers cite organizational misalignment, not technology, as their biggest barrier to transformation, this mindset is essential. Uptime means nothing if conversion is falling. A pristine data pipeline is useless if it doesn’t help a merchant forecast demand. AI initiatives fail not because models are weak, but because data quality is poor.
Janie and Jack’s turbulent ownership journey amplified this need for clarity. Acquired during Gymboree’s bankruptcy, integrated into Gap, then spun back out - the company was forced to rethink which systems to keep, which to replace, and which to retire entirely.
As Madhav explains, "Identifying the systems that overlap and then picking the right tool for the new integrated company is key when you're going through transitions."
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Strategic system selection during M&A: Integrate for value, not for uniformity
Most companies treat post-acquisition integration as an unavoidable mandate: consolidate everything into the acquirer’s stack. Bigger systems are assumed to be better systems.
Madhav rejected that logic.
Instead of integrating by default, he evaluated each system on one criterion: does this add measurable value to the business we’re becoming? The surprising truth? In many cases, the acquired systems were stronger than the parent’s.
Janie and Jack kept its best-in-class OMS, POS, and ecommerce stack, while strategically modernizing ERP, PLM, and data systems where it truly mattered. This selective integration preserved momentum, avoided unnecessary disruption, and created a modernization roadmap aligned with business outcomes.
The lesson for transformation leaders:
Don’t integrate because you can. Integrate because it creates demonstrable value.
The customer-facing first principle: Why rebuilding POS was the true starting point
With five years of deferred investment, Madhav could have begun anywhere - ERP, data warehouse, PLM. But he made a surprising move: modernize customer-facing systems first.
Why? Because legacy POS was directly harming customer experience and therefore revenue.
Old, register-based POS terminals meant store associates were stuck behind the counter instead of guiding customers. They couldn’t check inventory on the floor. They couldn’t create personalized experiences. They couldn’t transact anywhere except one fixed point in the store.
In a premium brand where in-store experience is core to value, this wasn’t a mild inconvenience. It was a revenue leak.
Upgrading to mobile-first POS transformed store operations overnight:
- Associates became consultants, not cashiers
- Customers were served anywhere, not just at checkout
- Real-time inventory became accessible across channels
- Personalized guidance became possible on the floor
This single modernization accelerated conversion, increased basket size, and improved satisfaction - creating early proof points that built confidence across the executive team.
The uptime paradox: Why operational stability isn’t a success metric
Traditional IT celebrates 99.99% uptime. Madhav challenges that outright:
“What’s the purpose of having a 99.99% uptime if the conversion is down?”
— Madhav Kondle, CIO of Janie and Jack
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This is the mindset shift defining next-generation CIO leadership.
Madhav built KPIs around:
- Conversion rate
- Revenue per visit
- Operational efficiency
- Time-to-launch for new initiatives
- Data quality supporting personalization and AI
This shift repositioned technology from a cost center to a commercial growth driver and reframed IT as a partner, not a support function.
Building a scalable, acquisition-ready platform
Janie and Jack wasn’t just modernizing, they were preparing for future brand acquisitions, including Hatch Collection. That meant creating a platform architecture capable of absorbing new brands quickly and cleanly.
Madhav’s blueprint centered on:
- Composable systems
- Clean data architecture
- Modular POS and OMS
- Flexible ecommerce storefronts
- Cloud-first infrastructure
This approach allowed the team to onboard Hatch seamlessly - validating the long-term scalability of the modernization strategy. And with FY26 focused on international expansion, opening the brand’s first London store, and supporting investors’ push to acquire more premium labels, building a platform that can integrate new brands effortlessly has never been more critical.
The bigger picture
Digital transformation often sparks fear - fear of disruption, fear of cost, fear of losing control. Madhav’s journey proves the opposite: when executed with clarity, discipline, and business alignment, transformation becomes a competitive advantage.
By prioritizing customer-facing wins, aligning metrics with commercial outcomes, and modernizing the tech stack without blind uniformity, Janie and Jack built a foundation strong enough to support premium brands today and flexible enough to power acquisitions tomorrow.
Want to hear more from Madhav Kondle on building scalable retail technology and navigating complex transitions? Listen to the full episode of the Ecommerce Toolbox: Expert Perspectives on your favorite podcast platform.
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