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SaaStr’s own Jason Lemkin shares the top 10 mistakes he sees during the hiring process during Workshop Wednesday, held every Wednesday at 10 a.m. But for a non-sales or marketing product, a tech or development product, or products that are more complicated than the last sale are likely to implode because they can’t learn it on the fly.
During one of our BIG RYG Hyper-Workshops on budgeting for Customer Success headcount, Kristen Hayer of The Success League, framed this shift by explaining that as a CS leader, you’re not running a happiness team, you’re running a revenue team. Your team will start to get pushed on the money side of things.
Sam Blond and Jason Lemkin joined together for a live SaaStr Workshop Wednesday looking at what has and what hasn’t changed in 2025 in GTM in general and in the age of AI. Wiz discovered a direct correlation between territory size and productivity: the tighter the territories, the more effective their sales team became.
At the time, expansion and upsell were handled by the CS team, whose primary focus was retention and customer success, not sales. The fix: moving upsell and expansion to a dedicated sales team. While aggressive hiring can be tempting, a learning from Levelsets growth was the importance of hiring for leverage, not headcount.
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