RetailCraft 57: "1300 entrepreneurs" - in conversation with Oskar Jacobsson, Director Customer Solutions, ICA Gruppen

What happens when one of the Nordics’ largest grocery retailers empowers 1,300 local entrepreneurs under a single national brand? In this episode, Ian Jindal chats with Oskar Jakobsson, Director of Customer Solutions at ICA Gruppen, to explore the unique federated model in Swedish grocery retail. Oskar shares how ICA balances entrepreneurial autonomy with digital innovation, discusses the challenges of unifying customer experience across diverse store formats, and reflects on the accelerating pace of change in retail technology. The conversation ranges from handwritten signs and local flavour to AI-driven personalisation, the future of agentic shopping, and the enduring joy of simply strolling through great stores.

About the Guest

Oskar Jakobsson is Director of Customer Solutions at ICA Gruppen, where he leads a team of nearly 200 colleagues responsible for all digital customer-facing touchpoints. With over 20 years’ experience in retail, spanning SaaS suppliers, H&M, and Sweden’s alcohol monopoly, Oskar brings deep expertise in digital transformation, customer experience, and the art of retail.

Key Topics & Timestamps

• 00:00 – Welcome & Introduction Oskar’s retail journey, passion for the industry, and why he loves just being in stores.

• 03:00 – ICA’s Unique Model: 1,300 Entrepreneurs How ICA’s structure empowers local ownership, creates lively, differentiated stores, and fosters community connection.

• 08:00 – Store Formats & Family Businesses The four ICA formats, from small convenience stores to hypermarkets, and the generational, entrepreneurial spirit behind them.

• 10:00 – Digital Customer Experience at Scale Oskar’s role in orchestrating all digital touchpoints, from apps to in-store tech, and the challenge of aligning with retailer-facing systems.

• 13:00 – Defining “Best Customer Experience” How ICA uses surveys, A/B testing, and constant feedback to keep the customer at the centre of every digital and in-store decision.

• 15:00 – The Complexity of Grocery Shopping Journeys Why food retail is uniquely challenging, and how ICA leverages data for relevance and personalisation.

• 17:00 – Retail Media, Promotions & Data The balance between central campaigns and local autonomy, and how ICA navigates data sharing and privacy in a federated model.

• 20:00 – The Pace of Change & Flexible Architecture Reflections on the rapid acceleration of retail tech, the need for adaptable IT infrastructure, and lessons from past digital transformations.

• 25:00 – AI, Agents & The Future of Grocery Oskar’s take on the coming wave of agentic shopping, the importance of brand trust, and how AI will reshape both online and in-store experiences.

• 31:00 – AI in Practice at ICA From classic analytics to generative AI and Microsoft Copilot, ICA is using AI for efficiency, decision support, and behind-the-scenes innovation.

• 34:00 – Advice for Retail Technologists Oskar’s career lessons: prioritisation, embracing change, and the value of curiosity and continuous learning.

• 39:00 – Getting Re-energised by Great Retail Why Oskar strolls malls for inspiration, and the importance of reconnecting with what makes retail exciting.

• 40:00 – What’s Next: Strategy & Direction The excitement of strategic planning, aligning teams, and setting direction for ICA’s future.

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Standout Quotes

“ICA isn’t a chain. It’s almost 1,300 separate retailers… Each st