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Chronicles

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Microsoft dealmaker Bruce Jaffe going startup

While Microsoft has yet to come up with a search engine that wows consumers, it has successfully wooed Wall Street with its push into online advertising.  Alas for Microsoft, it's losing a key dealmaker.  Bruce Jaffe, a top corporate-development executive …

Valleywag Owen Thomas

Context & Ripple Effects

Bruce Jaffe's exit lands in the middle of a rough stretch for Microsoft's consumer-facing ambitions. The company's top search executive had already left in March 2007, and by mid-year a Silicon Valley team was reportedly building a stealth search engine to close the gap with Google. What has worked instead, per the confirmed reporting, is the advertising push that won over Wall Street even as consumer search lagged.

Jaffe ran the corporate-development machine behind that strategy — he was the acquisitions point man whose departure MarketWatch also picked up — and he leaves one day after Microsoft announced its $1.2 billion acquisition of Norway's Fast Search & Transfer, part of a renewed challenge to Google and IBM in enterprise search.

First-order effects

  • Microsoft loses its lead dealmaker while an acquisition agenda is actively running — the Fast Search deal closed January 8, and integrating it plus any further ad-market purchases now falls to whoever inherits the role.
  • Jaffe exits at the top of his franchise rather than after a stumble, trading a corporate-development seat for a startup bet of his own.

Second-order effects

  • Succession risk compounds: with search leadership already churning since 2007, Microsoft must rebuild both product and M&A leadership simultaneously while competitors exploit the perception of drift.
  • Every senior operator who leaves a platform incumbent to found a firm becomes a competing buyer of talent and targets in the same startup market Microsoft's own dealmaking depends on.

Third-order effects

  • If departures like this keep tracking the search-and-advertising wars, the pattern points toward incumbent platforms losing their most experienced strategists precisely when competitive pressure peaks — weakening the internal capacity that large-scale M&A requires.
  • The episode feeds the broader question of whether Microsoft's ad-driven Wall Street narrative can survive continued attrition on the consumer-search side where the revenue actually gets contested.

The trend: As the search and online-advertising wars intensify, senior dealmakers and product leaders are leaving platform incumbents like Microsoft to launch their own ventures.