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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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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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The 3 Secret Ingredients for Scaling to $100M ARR with Bitly CEO and CPO

SaaStr

Bitly CEO Toby Gabriner and CPO Kelsey Stevenson share the three secret ingredients that helped them when scaling to $100M ARR and what they could have done differently. Around 2012, the focus became solely on the Enterprise, which is interesting considering they had a full-blown PLG engine. Bitly had an Enterprise sales-focused team.

Scale 306
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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. What should you look for in an Enterprise rep vs. a Mid-Market rep?

Scale 278
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Scaling Faster, An AMA with SaaStr Founder & CEO Jason Lemkin (Pod 577)

SaaStr

Jason recently opened up an AMA on Twitter Spaces to answer questions about how to scale faster. Those are all a bit enterprise biased. And I’ve watched them fairly quickly scale, to soon they’ll be at 10 million in revenue. As they scaled, they radically changed how they did sales. Jason Lemkin: Okay.

Scale 277
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Scaling from $1 to $10M, an AMA with SaaStr CEO and Founder Jason Lemkin (Pod 573)

SaaStr

Jason recently opened up an AMA on Twitter Spaces to answer questions about scaling from $1M to $10M. We did a good AMA on this scaling at SaaStr Europa in Barcelona, a couple weeks back. That will scale, and then take those emails after four great pieces of content and do a weekly webinar and do a weekly get-together for them.

Scale 298
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20 YC Startups Demoing at SaaStr 2025 Pushing the AI Frontier! From Abundant AI to Mosaic to Veriflow and More!!

SaaStr

Companies can meet stringent quality requirements at a fraction of the cost of in-house teams, while accelerating their AI initiatives. Why It Matters : Customer support teams are drowning in tickets, with resolution times getting longer, not shorter. All while maintaining 90% customer satisfaction score.

AI Search 178