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How to Train Your Sales Leaders: Key Learnings from HubSpot and BILL with Michelle Benfer

SaaStr

Former Head of Revenue at BILL and HubSpot Americas leader Michelle Benfer recently joined us on a SaaStr Workshop Wednesday share her insights on one of the most critical roles in any SaaS organization: the frontline sales manager. “At HubSpot, I had over 100 frontline sales managers reporting to me.

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AI, Sales + GTM in 2025/2026: This Changes Everything with Jason Lemkin and Owner CRO Kyle Norton

SaaStr

At SaaStr + AI Summit 2025, Jason Lemkin and Kyle Norton CRO of $1B+ vertical SaaS leader Owner (where Jason is on the board) did a deep dive on AI in Sales today. By the end of this quarter, team members who aren’t genuinely AI-curious should be let go. The 50/50 Team Is Coming Fast. And where it will be very soon.

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Is AI Penetration … Slowing Down? Ramp Says Possibly

SaaStr

The shift from “innovation budget” to “operational budget” means AI tools must compete directly with established software investments—and many aren’t winning those comparisons yet. Companies are discovering that hiring AI talent or upskilling existing teams takes much longer than anticipated.

AI 269
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The $939B Question: Is AI Eating SaaS or Feeding It?

SaaStr

The Billion-Dollar AI Unicorn Factory The scale of AI startup funding isn’t just impressive — it’s existential for SaaS: The AI Billion-Dollar Club: OpenAI : $8.4 billion valuation after 175M round Scale AI : $29 billion valuation / “sale” with Meta’s $14.3 billion in funding xAI : $6.4

AI Search 233
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Scaling Success: Digital Entrepreneurship and SaaS Exits

FastSpring

Listen for the full insights into: How Flippa.com works to connect for-sale businesses with buyers while managing the complexities of valuation and seller expectations. How selling an investment business is very different from getting VC funding. And that’s substantial scale in. That’s now a billion dollar company.

Scale 118
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Okta’s Playbook to PLG, Developer Experience, and Enterprise ARR

SaaStr

Okta’s VP of Engineering, Monica Bajaj, and Senior Director of Platform Product Marketing, Priya Ramamurthi, share Okta’s playbook to PLG, developer experience, and Enterprise ARR. Product-led outperformers generate ten percentage points higher in ARR and 50% higher in valuations than sales-led growth outperformers.

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How Revenue Leaders at Box, Calendly, and Lattice Scaled From $0 to $100M+ and Beyond

SaaStr

Mark Roberge , SaaStr fan-favorite and Co-Founder and Managing Director of Stage 2 Capital brought together some of the top CROs in SaaS during the SaaStr Annual to share some of their greatest learnings and pivotal moments leading some of the Cloud 100 SaaS companies. The bad news is it wasn’t driving the results they wanted.

Scale 271