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Sill first entered show business as a nightclub owner, but in 1945, he joined the sales and promotion staff of the [[Bihari brothers]]' [[Modern Records]], first as a regonal sale manager and then producing sessions for R&B acts including [[Charles Brown (musician)|Charles Brown]] and [[Hadda Brooks]].<ref name="Talevski 2010 p. 592">{{cite book | last=Talevski | first=N. | title=Rock Obituaries: Knocking On Heaven's Door | publisher=Music Sales | year=2010 | isbn=978-0-85712-117-2 | url=https://books.google.com/books?id=DykffzkFALoC&pg=PA592 | access-date=2019-11-07 | page=592}}</ref> Sill shepherded the fledgling career of the songwriting team of [[Jerry Leiber and Mike Stoller]]. In 1950, Sill met Leiber at Modern Records,<ref name="Palmer 1978">{{cite book |last= Palmer |first= Robert |date= 1978 |title= Baby, That Was Rock' N Roll |location= United States |publisher= A Harvest / HBJ book |page= <!-- or pages= --> |isbn= 0156101556 |author-link=}}</ref> where the aspiring lyricist worked as a retail clerk and suggested he find a partner who could read and write music, spurring the beginning of Leiber's collaboration with Mike Stoller.<ref name="Simpson 2003 p. 135">{{cite book | last=Simpson | first=P. | title=The Rough Guide to Cult Pop | publisher=Rough Guides | series=Music rough guide | year=2003 | isbn=978-1-84353-229-3 | url=https://books.google.com/books?id=F7hpXcrqA-8C&pg=PA135 | access-date=2019-11-07 | page=135}}</ref> Sill produced the 1951 [[Jimmy Witherspoon]] effort "Real Ugly Woman"," the first recorded Leiber and Stoller collaboration.<ref name="Simpson 2003 p. 135"/>