Publisher Faber gave Freedman his first major commission, an assignment to design and illustrate Siegfried Sassoon's Memoirs of an Infantry Officer. Published in 1931, the book was the subject of controversial reviews but brought him into prominence. Freedman had by that time become interested in the difficult medium of auto-lithography, where the artist draws his own designs on to the stones without the intervention of a trade craftsmen or photomechanical means. Freedman received advice from T. E. Griffits, the most influential lithographer of the time, who held sway at Vincent Brooks, Day & Son.
Following work on an annual report for the Post Office, Freedman was chosen to design the 1935 postage stamp issues to commemorate the Silver Jubilee of King George V. The distinctive and handsome nature of this work brought him to wider public notice. His work - which took him just a weekend - and the subsequent printing of the stamps was the subject of The King's Stamp, a documentary film by the GPO Film Unit. Freedman also designed Jubilee postal orders, in various values from sixpence to £1. Freedman was now recognised as a force in autolithographic printmaking, and his down-to-earth attitude and lack of pretension made him welcome among the craftsmen at the Curwen Press, the Baynard Press and Chromoworks, the leading firms in the industry. For the Baynard Press, he also designed the Baynard Claudia typeface, which he named after his wife, Beatrice Claudia Guercio. Guercio was also an artist of some repute and had herself been commissioned to design a new GPO greetings telegram to commemorate the 1937 Coronation of George VI.