Rob was part of Tenzing’s first Sherpa cohort in 2020. He started at Activpayroll and then PSSG, working on the core operational lead-to-cash systems that would underpin the next phase of growth. He has always had a tech and operations leaning, and it did not take long for him to become the person everyone wanted to look at their processes and systems.
In May 2021 he moved from the portfolio into the Growth Team as Subject Specialist on internal technology. He spent three to six months with new investments, helping turn operating models into smoother, more scalable machines — CRM, employee lifecycle, vendor selection and the whole lead-to-cash process. From January 2023 he joined the core Tenzing team as Head of Technology, making sure the Firm had tools that were easy to use, secure and fit for a growing platform, while continuing to support the portfolio on cybersecurity governance and systems architecture.
Rob left Tenzing in 2025 and founded Patching, where he works with founders and business owners looking to ensure they have solid technology foundations that will be an asset rather than a liability when they start an exit process: robust foundations, proportionate security, and practical AI that runs securely inside the business. He remains part of the Sherpa Alumni community and is always happy to be a sounding board for current Sherpas and portfolio teams.
He started his career in the Army, where his character was shaped by the streets of Iraq and the deserts of Afghanistan. Keen to leave whilst still in one piece, and young enough to start again, he followed the well-trodden path into Investment Banking Operations. Independently minded and feeling constrained by another large organisation, he struck out on his own, started a tech business and learned about entrepreneurship and failure the hard way. He then joined a promising health-tech business as an early employee and built a connected medical hardware supply chain from scratch, scaling it to 40+ countries and double-digit million revenues.
The day-to-day operations of any modern business are a function of their systems, and how processes and people fit around those capabilities or limitations. Having the chance to look inside a lot of high-growth PE-backed businesses, and then to help design the architecture that lets them scale, is still one of the most interesting jobs there is. Tenzing was a rare place to do that work — and the Sherpa Programme was the springboard.
– Rob Tregaskes, Sherpa Alumni and Founder of Patching
