A new breed

In response to inflexibility in the industry, Jessica has carved the way for a new breed of accountants, proving by her own success that modern, client focused, family friendly practices also make good business sense.

As managing director of Pillow May and as a thought leader, speaker, expert adviser, software consultant, not forgetting mum of two,  Jessica continues to be a force for positive change in the industry.


Women in Accountancy and Finance Awards 2020 – May 6th 2020

Jessica Pillow – Finalist in Woman of the Year – Practice (Small)

Shelley Pritchard – Finalist in Role Model of the Year – Practice (small)



Technology for a better life

Jessica has been at the forefront of the digital revolution, advocating cloud accounting software from its inception. A strong advocate for using technology to enable efficient, flexible working, her views on the benefits of a flexible workforce have had industry wide influence; and her expertise is now greatly sought after.

She is currently working with a leading accountancy software provider on a consultancy basis.

lnfluence and know how

Jessica is a Chartered Accountant, Chartered Tax Adviser and respected business adviser, whose strategic advice and mentoring has enabled some fantastic small businesses to grow. Read one of her success stories here.

An industry speaker and panel expert for FreeAgent, Receipt Bank and Xero; Jessica regularly features at conferences such as Xerocon, Alternative IT and Synergy Conference. She’s also a contributing author for the ICAEW magazine.

Jessica’s view

  • 11 October 2019

The latest IR35 case law

This article highlights some of the latest IR35 cases, and uses what we’ve learned from them to draw up a list of the most influential factors.


  • 01 February 2019

Remote possibilities

Jessica looks at the management challenges of moving to a cloud-based accounting practice.

  • 07 November 2018

How not to fall prey to a cyber attack

A very personal account of why cultivating a culture of questioning to fight fraud is vital.

Connect with Jessica