Mon.May 26, 2025

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On Insularity

Partners in Excellence

We live in overlapping circles on “Insularity.” Our families, friends, communities. Our teammates, functions, organizations, industries. These insular communities provide us different levels of security and comfort. From a professional point of view, they are made up of people doing similar things, facing similar issues/challenges. While we may compete with each other in the markets, we learn from each other, see differing approaches, sometimes seeing new opportunities.

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The 2026 Sales Team: 50% Humans, 50% AIs. All 1 Team.

SaaStr

We’ve already seen something happen in support. You can’t automate 100% of support with AI yet. At least, not reliably. But you can automate 30%-40% of support for real … with top 10% CSAT. So what does that mean for inside sales? Probably something similar by 2026. A 50/50 Sales Team. 50% of your team are humans. 50% are AI. At least for SMB and more routine mid-market sales.

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How sales, training, and revops leaders use learning analytics to boost results

Highspot

Key takeaways Learning analytics connects training investments directly to business results, helping teams prove impact and make faster, smarter decisions. Sales enablement, training, and RevOps teams can leverage analytics tools uniquely. 61% of high-performing organizations actively monitor performance metrics , while less than one-third of low performers do.

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Dear SaaStr: Our Champion Left The Company. How Do I Ensure a Shaky Deal Doesn’t Collapse?

SaaStr

Dear SaaStr: Our Champion Left The Company. How Do I Ensure a Shaky Deal Doesn’t Collapse? When your champion leaves, youre essentially starting from scratch with the account. Youve lost your internal advocate, and now you need to rebuild trust and prove value to the new stakeholders. Heres how you can stabilize the deal and prevent churn: Treat it like a brand-new deal.This is critical.

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Welcome to the Future of Hospitality: Smart Rooms Start Here

Speaker: Jady West, VP of Hospitality & Chris Bennett, Head of Sales & Engineering

The modern hotel room is no longer just a place to stay—it’s an experience to remember. Today’s guests expect seamless 5G connectivity, personalized comfort, and high-tech convenience. From AI-powered smart room controls to in-room entertainment and app-based services, technology is redefining hospitality from the inside out. In this new session featuring industry pros Jady West and Chris Bennett, we’ll explore how high-speed, high-bandwidth connectivity powers the innovations that are enabling

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How I get fired up for my cold calls, insights from my 18 years in sales (+ tips for reps)

Hubspot

When I was in 5th grade, I was voted Most Reserved in the yearbook at Dewey Elementary School in Cherry Hill, NJ. I had just moved back to Jersey after bouncing around SoCal. I was a shy kid, nervous about making new friends. No one would expect me to go into sales, a field thats all about forging new relationships. Yet, I started my career in sales at 19 years old.

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Perplexity’s CBO: Speed is The New Moat in AI Sales

SaaStr

New!! @perplexity_ai 's CBO @dmitry140 + @samdblond on AI in Sales: You Must Move Much Faster – No excuse to not be moving much faster than 12 months ago – Every question you'd ask in a meeting you can just ask an AI in advance. No excuses. – No excuses to be doing pic.twitter.com/NWjVbLL71C — Jason SaaStr.Ai Lemkin (@jasonlk) May 24, 2025 Perplexity’s CBO Dmitry Shevelenko joined Sam Blond ex-CEO of Brex at 2025 SaaStr + AI Summit for a deep dive on AI and