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The Top 10 Mistakes People Make When Hiring a VP of Sales with SaaStr CEO and Founder Jason Lemkin

SaaStr

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.

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Where Is Customer Success Headed in 2022?

ChurnZero

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.

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Sam Blond + Jason Lemkin “GTM in 2025: How It’s Changed, How It’s Changing, and What Hasn’t Changed (Yet)”

SaaStr

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.

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How Levelset scaled to $25M ARR, then sold for $500M

Sales Hacker

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.

Scale 69