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Dear Quota Team,

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My company just offered me a promotion to regional sales manager, overseeing 12 reps across three states—something I've worked toward for years. The same week, a former colleague approached me about joining his new venture capital firm as a "sales enablement partner," helping their portfolio companies scale their sales operations. The VC role pays less initially but offers exposure to multiple industries, equity stakes in various startups, and potential pathways into investing. Do I take the traditional management promotion I've earned, or pivot into this unique hybrid role that could open doors I never imagined but has no clear precedent for success?

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Deciding in California 

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Dear Deciding,

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The VC opportunity presents a rare chance to leverage your sales expertise in a completely different arena with higher upside potential — these roles don't come around often and could fundamentally change your career trajectory. However, consider your risk tolerance and financial obligations: the management role offers predictable advancement and proven income, while the VC path is essentially a startup bet with your career. If you can afford the initial pay cut and uncertainty, the VC role's exposure to multiple companies, equity opportunities, and potential transition into investing could be huge, not to mention a great learning opportunity. Ask yourself which job you'd regret not taking in five years — that's usually your answer.