Inside a 5-year tech gap: How Madhav Kondle upgraded Janie and Jack’s 17-year-old systems

Rebuilding retail tech isn’t just about shiny, new tools and platforms, it’s about creating a foundation that accelerates growth, integrates acquisitions seamlessly, and gives every team a single version of the truth. And Madhav Kondle, CIO of Janie and Jack, did just this. In this conversation, he reveals how he executed a company-wide technology overhaul following a major spin-out. When Madhav stepped in, the stack was years behind - legacy POS, broken data pipelines, disconnected ecommerce systems, and a backlog of tech debt that had compounded since 2017.

And Madhav Kondle, CIO of Janie and Jack, did just this. In this conversation, he reveals how he executed a company-wide technology overhaul following a major spin-out. When Madhav stepped in, the stack was years behind - legacy POS, broken data pipelines, disconnected ecommerce systems, and a backlog of tech debt that had compounded since 2017.

In just two years, Madhav rebuilt the company’s entire ecosystem - modernizing POS, OMS, and ecommerce with Salesforce and Snowflake, unifying all omnichannel data into a single warehouse, eliminating the dashboard inconsistencies that frustrated merchandising, finance, and marketing, and shifting C-suite reporting from technical uptime to the business KPIs that actually drive revenue.

So, if you're navigating M&A transitions, eliminating data silos, modernizing legacy retail infrastructure, or trying to build an analytics foundation fit for AI, this episode gives you a blueprint for doing it right.

What You’ll Learn

How to evaluate systems during M&A transitions: When to adopt the acquirer’s stack, when to retain best-in-class tools, and how to avoid unnecessary system consolidation.
Why legacy tech debt compounds faster than most leaders expect and how to prioritize modernization without breaking the business.
How to shift C-suite conversations from technical KPIs to business KPIs, aligning technology directly to revenue growth.
The blueprint for creating a single source of truth across POS, ecommerce, marketing, and operations using Salesforce OMS + Snowflake.
Why clean, consistent, semantically aligned data is the true prerequisite for GenAI, not models or tooling.
How to architect scalable, acquisition-ready platforms that can onboard new brands quickly and cleanly.
The importance of sequencing system transitions, starting with customer-facing touchpoints before reworking backend infrastructure.
How to eliminate the “different numbers in different dashboards” problem that slows decision-making and creates cross-functional misalignment.

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