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My Weird Prompts · August 14 · 26 min

Software Evaluation as a Career Path

What do you call someone who loves deep-diving into software options, building evaluation matrices, and becoming the person everyone asks "which one should we buy?" In this episode, we map a career path that's surprisingly ill-defined for how much it matters. We break down the three tiers of software evaluation roles—from in-house procurement to external advisory at firms like Gartner and Forrester—and look at salary data for 2026. We also unpack how the build-versus-buy decision changes at different company sizes, why 78% of large organizations prefer buying over building, and how compliance overhead is reshaping the entire landscape. Plus, we explore the emerging category of the AI-augmented evaluator and what that means for the future of the field. Episode #851829 — open it directly at myweirdprompts.com/851829

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What do you call someone who loves deep-diving into software options, building evaluation matrices, and becoming the person everyone asks "which one should we buy?" In this episode, we map a career path that's surprisingly ill-defined for how much it matters. We break down the three tiers of software evaluation roles—from in-house procurement to external advisory at firms like Gartner and Forrester—and look at salary data for 2026. We also unpack how the build-versus-buy decision changes at different company sizes, why 78% of large organizations prefer buying over building, and how compliance overhead is reshaping the entire landscape. Plus, we explore the emerging category of the AI-augmented evaluator and what that means for the future of the field.

Episode #851829 — open it directly at myweirdprompts.com/851829

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