For years, software CEOs courted his goodwill but lived in fear of his pronouncements. Charles ‘Chuck’ Phillips, the lead enterprise software analyst at investment bank Morgan Stanley, commanded such respect – from investors, from software industry management, and, indeed as a former data processing executive himself, from CIOs – that few ever called into question his judgement.

That was until mid-May. After years of fierce independence, the 43-year-old former Marine quit Wall Street to take up the singular position of ‘executive VP in charge of customer-facing activities in the office of the CEO’ at software giant Oracle – a company whose fortunes he tracked (and influenced) for the best part of his 17 years as an analyst. Throughout that period Phillips was certainly well informed.

Weeks before his surprise move, Information Age profiled Phillips and highlighted how his advice to investors drew heavily on the in-depth polling of the spending plans of 250 of the world’s top CIOs – contacts Morgan Stanley had cultivated over the years. Now Oracle, implicitly admitting it needs to align its product strategy more closely with customer needs, has asked Phillips to lead an intelligence gathering operation to do the same, helping it to better channel its R&D cash.

Looking back through Phillips’ past reports on Oracle, though, perhaps the writing was on the wall:

“The good news is that Oracle is there with [a CRM] suite, while its competition is largely absent from this higher growth market…Oracle’s applications business is holding up better than the pack.” (March 1999)

“We think Oracle’s competitive position is its strongest ever.” (Sept 1999)

“They’ve done a masterful job of consistently hammering home [the Internet] theme.” (October 2000)

“The tech industry will evolve into a small number of companies that corporations buy their software from – and Oracle is one of them.” (Nov 2002)