Sherpa at PSSG

Rob Tregaskes

Rob is our Sherpa supporting PSSG. He works directly with Eric and the Board improving the core Operational Lead to Cash systems in the company, creating the foundations for accelerated growth.

Rob is one of our first cohort of Sherpas and is the techie ops guy; he loves making businesses into smooth-running, scalable machines and getting stuff done, often with technology.

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 the Army whilst still in one piece, and young enough to start a new career, he followed the well-trodden path into Investment Banking Operations. Independently minded and feeling constrained by another large organisation, Rob decided to strike out on his own, starting a tech business and learning about entrepreneurship and failure the hard way. He then joined a promising health tech business as an early employee and hasn’t looked back – building a connected medical hardware supply chain from scratch and scaling it up to shipping to 40+ countries and delivering double-digit million revenues.

Rob was seeking a new challenge when the opportunity of building the Sherpa programme as an early Sherpa presented itself. As a company builder who shies away from the spotlight and likes to get stuff done quietly, it was the perfect opportunity.

Like any innovative growth focussed role, being a Sherpa has its ups and downs. But the opportunity to influence and shape some of a business’s most strategic growth initiatives, backed up by the incredible talent and support of Glenn, the other Sherpas and the broader Tenzing Growth network, is a rare luxury I am very grateful for.

– Rob Tregaskes, Sherpa at PSSG


  • Spending time with family and close friends
  • Working with great people
  • Reading about business, technology and strategy
  • The sea (on/next to it) and mountains (coming down them, quickly)



  • He uses emojis way too much