DITT Talk: Tax Technology

In this episode, host Shan Sun sits down with Russell Gammon, Chief Innovation Officer at Alphatax, to explore what it actually means to build generative AI into core tax software. They discuss how automation is reshaping daily tasks, the changing approach to training junior staff, and what success looks like as AI transforms tax teams globally.

Discover how adaptable tax professionals can thrive, why human oversight and strategic thinking will take centre-stage, and what the tax jobs of the future will look like.

In this episode, Shan Sun, our host of DITT Talk and a committee member of the Diploma in Tax Technology (DITT), speaks with Graham Tilbury and Stephen Callahan from BCT Partners about how AI governance is necessary in the world of tax technology. They discuss how traditional risk-management frameworks are adapting to the speed of AI, and what HMRC's new rules on adviser conduct mean for tax professionals and finance leaders.

Discover why human judgment is still the most important safeguard against AI errors, and learn how to proactively manage the risks of using AI tools in your day-to-day tax work.

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.

Shan Sun, Tax Technology Lead, Deliveroo and Liz Gallagher, Indirect Tax Director, Meta explore cross-border tax challenges and major regulatory or technology progress that has shaped the indirect tax landscape.  They also discuss fostering collaboration between tax and technology teams, despite complex compliancy issues.

Guest speaker Erica Perry, UK Head of Transfer Pricing KPMG discusses how Machine Learning and Artificial Intelligence is used in Transfer Pricing, as well as future trends in the space of Transfer Pricing adopting technology.  

Shan Sun talks to Alexander Kobakhidze (Ako) investigating why tax technology is critical in today’s business environment, and when is the best time for a business to think about getting a tax technology team. They consider how the tax tech role is evolving in light of AI machine learning and workflow automation tools introduced into the market.

Hosted by Shan Sun, Tax Technology Lead, Deliveroo is joined by guest speaker Pablo Sprechmann, Staff Research Scientist, Google DeepMind explores:

• Advancements and trends in AI

• Practical applications of AI in taxation

• Ensuring accuracy and transparency in tax AI applications

• AI impact on the future of taxation.