Episode 112

Janie and Jack: Turning retail tech into business growth

Madhav Kondle
Madhav Kondle
Chief Information Officer

In this episode we talked about:

  • 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.

🎧 Listen now on Apple Podcasts, Spotify, or YouTube

Episode highlights:

01:56 – Spinning out from Gap: Technical lessons in separation

03:56 – Rebuilding the tech stack: POS, OMS, ERP & data overhaul

05:50 – From foundations to optimization: What comes next

06:53 – Business-first KPIs: Why CIOs must think like operators

08:25 – Unifying data: POS, ecommerce, and customer 360 in Snowflake

15:43 – GenAI’s real role: Insights over instant answers

Madhav's bottom line: Focus on business impact, not tech for tech’s sake. Build a unified, reliable data foundation, choose systems that enable scale, and ensure every technology decision supports traffic, conversion, basket size, and customer value.

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