DITT Talk: Tax Technology

In this episode Shan Sun, Tax Technology Lead at Deliveroo and Simon York CBE former HMRC FIS, J5 Lead discuss how HMRC uses data to protect revenue and improve services. Shan and Simon explore what HMRC’s “Connect” system + behavioural models mean for smarter, risk-based compliance. Also ethics, public trust, and data: where HMRC drew the line—and why it matters. If you work in tax, data, or public sector transformation, this one is packed with practical takeaways.

Our host Shan Sun, Tax Technology Lead, Deliveroo interviews two special HMRC guests Jonathan Athow, the Director General for Customer Strategy and Tax Design at HMRC and Paul Aplin, Deputy President of CIOT and Chairs the Diploma in Tax Technology Committee.  Jonathan and Paul provide insights into HMRC's Transformation Roadmap, its goal to be 90% digital by 2030 and the necessary steps to achieve that vision. They also discuss the complexities and main risks associated with the Single Customer Account.Finally, they delve into how HMRC is approaching AIintegration in a way that ensures fairness and maintains trust and aligns with the department’s wider accountability standards.

Shan Sun, Tax Technology Lead, Deliveroo and Evan Croen, Head of Bloomberg Tax explore the technical and data challenges when integrating generative AI into tax workflows. They also discuss how to balance cutting-edge technology with reliability and how to maintain alignment between technical development teams and product/business strategy.

In this episode, Shan Sun, Tax Technology Lead, Deliveroo and Anna Elphick, Global Head of Tax, Treasury & Insurance at Unilever Ice Cream dive into Unilever’s global tax transformation journey.  This includes setting up a centralised tax operations centre to driving efficiency, accuracy, and control across jurisdictions. Discover how strategic decisions, advanced technologies, and a focus on talent and compliance are shaping the future of tax. Packed with practical insights for tax leaders navigating change at scale.

Our host Shan Sun, Tax Technology, Lead Deliveroo and guest speaker Antonio Lanotte, Chartered Tax Adviser explore how blockchain technology is altering tax compliance and reporting, also tax implications on crypto-related activities.  They discuss common tax issues and pitfalls that individuals and businesses face when dealing with crypto-assets and how tax authorities track and monitor crypto transactions.