Navigating New Terrain – The Rise of the Entrepreneurial CFO: Tom O’Hara, Kick ICT Group

Rutherford Cross welcomed Tom O’Hara (CA), Chief Executive of Kick ICT Group, to speak at the latest boardroom lunch where the marked increase of entrepreneurial finance leaders in recent years was discussed.

We were delighted to partner with Lyn Calder, Managing Partner (Edinburgh) & Chief Growth Officer at AAB, to host a number of Scotland’s leading CFOs and Finance Directors for what proved to be a hugely enjoyable presentation and lively discussion.

Over recent years, the role of the CFO has evolved, transcending the financial function to embrace entrepreneurial ventures, operating as a strategic partner and key driver of growth. CFOs are now catalysts for change, unlocking new revenue streams, driving innovation, and identifying new commercial opportunities. We were fortunate to have Tom with us for a couple of hours, sharing his journey as well as valuable insights into how finance professionals can become the entrepreneurial leaders of the future.


The Journey

Tom’s early career started traditionally enough, graduating from Heriot-Watt University with a degree in Accountancy & Finance before training as a Chartered Accountant with what is now EY. His first finance job outside the profession was with a company called ComputerLand, which was subsequently acquired by the then-listed SkillsGroup plc. It was here that he started to move from the world of accountancy into a more commercial and business development role.

Tom’s entrepreneurial journey accelerated as he co-founded ISI Group, which purchased and created a number of businesses, including McLaren Consulting and Cadspace before selling them on to Private Equity at the height of the dot-com bubble. In 2002, Tom set up ISI Systems to acquire a Pegasus consultancy business, but within a year, a deal was agreed to sell ISI to TSG, the tech company started by Sage co-founder Graham Wylie, and Tom took on the opportunity to build the TSG business in Scotland for the better part of the next ten years.

Tom enjoyed many aspects of the TSG journey, however, it was at this time that he first discovered the art of “knowing when to go,” even though he had not contemplated, let alone fully planned, his next steps. However, after a year working as the Director of Finance & IT at a charity (Enable) during his restrictive covenant phase, he established Kick ICT in 2015, along with long-standing friend Alan Turnbull and colleague David Chazan.

Since its formation, Kick has swiftly become one of the UK’s leading providers of IT solutions, network infrastructure, and support, establishing itself as a distinguished leader in the IT-managed service industry through a blend of organic growth and strategic acquisitions. As the CEO of Kick, Tom has been instrumental in steering the company to quickly seize strategic market opportunities, a tactic that has led to the acquisition of nine companies to date. This dynamic approach under Tom’s leadership continues to shape Kick’s respected position within the industry, which has most recently led to new investment by LDC at the end of 2023, triggering a successful exit for BGF who invested £8.7m in 2021.



It was clear from the discussion that Tom’s journey resonated with many of the finance leaders around the table, especially those who have been involved in scale-up businesses which have either significant private equity involvement and/or are founder led. Certainly, many of the guests find their roles transcending the traditional finance responsibilities into areas such as business development, general management and, increasingly, into the new agendas of ESG, Data, and AI.

Tom attributes his successful business leadership transition to a blend of financial pragmatism, strategic vision, and common sense. This includes thorough documentation and data analysis, identifying potential acquisition targets, and maintaining positive relationships to facilitate future business opportunities.

Tom emphasised the importance of understanding the human element in managing companies and making acquisitions, recognising when one is best suited to lead. He often navigated the balance between talent and commercial reality, acknowledging that the smartest person may not always be the best leader. In essence, Tom underscored the critical ability to translate vision into practical action for the benefit of all shareholders.


Closing Remarks

Some of Tom’s key recommendations for our group included:

  • Recognise when you are losing control of your own destiny and know when to leave if you can no longer effect change
  • Build robust networks; maintaining positive relationships makes business easier and ensures future opportunities
  • Prioritise deals that benefit the collective, not just the individual
  • Ignore those who criticise without substance; their influence is already diminished
  • Conduct deals with trusted individuals and be ready to walk away if that trust is broken
  • Establish your boundaries early and adhere to them consistently


To find out more about our events programme, or to discuss how Rutherford Cross can help you or your business, please contact Mark Lewis on [email protected].