Transforming Sales: How to Sell Harder Products and Succeed

In this segment, Jason M. Lemkin argues that hiring salespeople who have experience selling more difficult, complex products yields immediate performance gains. He likens such hires to “weight being released from their feet,” because they have already mastered the challenges of selling hard-to-sell solutions. Lemkin illustrates the point with a concrete example: his first Sales Development Representative (SDR), Sam Blonde, who previously sold an online financial‑software product at Intact (later acquired for $1 billion). After joining Lemkin’s company, Blonde quickly excelled, later becoming CRO at Brex and now a partner at Founders Fund. The anecdote underscores the broader principle that a modest increase in product difficulty in a candidate’s prior experience translates into outsized sales effectiveness in a new, easier‑to‑sell environment.










