Cagan's claim that organizations already led by engineering are the easiest to move toward the Product Model (vs. Roadmap Model), because engineering already commands organizational attention and investment — unlike organizations that outsource engineering entirely (see Software Factory Delivery Model), which lack that internal foothold and must build credibility for the function from scratch.
When assessing how hard a transformation will be, check whether engineering is in-house and already influential — that's a head start, not a coincidence.
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