Gregory has worked in the rail industry for 17 years, the majority spent working in rail freight, since joining Network Rail’s Operations and Customer Service Graduate scheme back in 2009. Following the completion of the scheme, which included 'passing out' as a fully trained signaller, he joined Network Rail’s internal freight team, initially as a Route Freight Manager covering Anglia and South East before moving into a role managing the customer relationships with major end users as Port & Terminal Account Manager.

In 2015, Gregory moved to Colas Rail, a Freight Operating Company (FOC) as a Freight Customer Account Manager responsible for the commercial and operational relationship with existing and new customers. The latter responsibility included setting up new contracts such as the Scottish Tarmac cement flows. This role was followed by moving into a role as Performance & Policy Manager which included managing Colas’ Train Planning function.

In 2019, Gregory joined Rail Operations Group, a specialist FOC and Rail Services operator as Head of Planning & Resource managing the creation and output of the daily and weekly train plans. This was eventually followed by a move back into the world of policy as Head of Policy & Access.

The publication of the Williams Review on rail and the creation of the Great British Railways Transition Team (GBRTT) saw a unique opportunity for Gregory to undertake an industry secondment in the role of Freight Business Development Manager. This was followed by a permanent appointment to the role within the Network Rail Railfreight Team in 2024. This role involves working with the industry and both existing and new to rail customers to enable greater modal shift of freight to rail. This role is both varied and far reaching and covers everything for development of the land freight estate through to cultivating and using market intelligence to help inform key decisions. Successes to date have seen the re-establishment of mothballed freight terminals at Thorney Mill and Rugby into active rail served sites. 

As part of his work around developing new markets for rail, Gregory has been engaging and working with the wider industry and Government departments on developing the prospects of moving ‘new energies’ (hydrogen, Carbon Capture Usage & Storage and Sustainable Aviation Fuel) by rail as part of a Non-Pipeline Transport solution. In tandem, Gregory has been working on the 'Building Freight Britain' project which aims to identify, detail, focus and raise industry awareness on upcoming large-scale National infrastructure schemes and to help enable rail freight to successfully support the construction phase logistics solution.