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The Top 3 Reasons AI Sales Tools “Don’t Work” (Spoiler: They Actually Do)

SaaStr

✨ Lemkin (@jasonlk) June 16, 2025 The Top 3 Reasons AI Sales Tools “Don’t Work” (Spoiler: They Actually Do, If You Use The Tools Properly) I get this question at least 3x a week: “Jason, we tried AI sales tools and they just don’t work. I’ve been in B2B and Saa sales for 15+ years.

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The Early Days: How Deel Went From $1m to $100m ARR in Just 20 Months

SaaStr

The Pivot : They interviewed 200 companies and 400 founders in just 6 weeks, asking one simple question: “If you’re open to hiring internationally, what are your biggest challenges?” ” The Discovery : Companies didn’t just need payments—they needed payments plus compliance. ” Training was broken.

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Dear SaaStr: What Are Some Tips For Shortening Enterprise Sales Cycles?

SaaStr

Dear SaaStr: What Are Some Tips For Shortening Enterprise Sales Cycles? A bit more on that here : How to Cope With Long Sales Cycles But there are plenty of things that help : Hire a VP of Sales with Enterprise Experience : A great VP of Sales who’s closed deals at your price point can shave months off your sales cycle.

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The Early Days: 5 Things Vanta Got Right, And 5 It Got Wrong, Getting to First $10m ARR

SaaStr

5 Things Vanta Got Right and 5 They Got Wrong getting to the first $10m ARR When Christina Cacioppo co-founded Vanta in 2017, security compliance was an afterthought for most startups. billion with over 8,000 customers worldwide, having fundamentally transformed how companies think about trust and compliance. A color-coded spreadsheet.

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The Vertical SaaS Gold Rush: Why Non-Tech B2B Is Growing 250%+ Faster

SaaStr

A plumbing company isn’t hiring a Chief AI Officer. Regulatory Requirements Create Infinite Moats Try switching away from Toast when you’ve got 50 restaurant locations with integrated POS, payments, payroll, and compliance systems. Try replacing Samsara when it’s monitoring your entire fleet for DOT compliance.

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The Enterprise Journey: 8 Keys to Going Upmarket Successfully with Workiva’s CEO Julie Iskow

SaaStr

You need: Sales leaders who understand complex, multi-stakeholder deals Customer success teams ready for high-touch support Legal expertise for enterprise contract negotiation Product leaders who can balance current needs with future vision Pro tip: Hire enterprise reps in pairs. If both succeed, you’re ready to scale.

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The #1 and #2 Reasons I See Sales Execs Fail Today

SaaStr

When I look at the VP of Sales / CRO that didnt work out the past 12-18 months across the SaaStr Fund portfolio and my ecosystem, one thing stands out. And its an old SaaStr theme: #1: You have to hire folks in sales where their last job was harder. Security compliance? There may exceptions at rocketships. Voice APIs?