by Jason Lemkin | May 27, 2026 | Blog Posts, Early, Sales, Sales |
A while back on LinkedIn and Twitter we had over 200,000 views and engagements on a quick post on “The Magical Sales Rep”, and another 500+ likes on a follow-up. It’s worth a deeper dive. Especially now in 2026, where the role of that first rep has...
by Jason Lemkin | May 26, 2026 | Artificial Intelligence (AI), Blog Posts, Sales
At SaaStr AI 2026, Kyle Norton, CRO of vertical AI leader for restaurants Owner.com, walked through how his team is generating outcomes that look almost impossible on paper for traditional B2B. Owner sells vertical AI to independent mom-and-pop restaurants (think...
by Jason Lemkin | May 26, 2026 | Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
So I spent the other day writing a fairly dark post about how most traditional B2B leaders will slowly atrophy to nothingness. Maybe seven survivors, everyone else decays, Medallia as the cautionary tale, but just one of many: Medallia Is Just the Opening Act: 12+ PE...
by Jason Lemkin | May 25, 2026 | Blog Posts
We’ve now rolled out 21+ AI agents and 12+ vibe coded apps at SaaStr AI, used 1,100,000+ times. AI SDRs. An AI VP of Marketing (10K) that in many ways now manages us, not the other way around. AI-powered VC tools that have run over a million startup valuations....
by Jason Lemkin | May 25, 2026 | Blog Posts |
So when I look back on my many failings as an entrepreneur, in the end, it’s all about the team. Almost all my failings as a CEO and founder came from failing to get that one extra great VP hired, that one critical hire. And cofounder is the most complicated of all....
by Jason Lemkin | May 24, 2026 | Early
Every B2B company right now is staring at the same problem: they need more Forward Deployed Engineers, they don’t have enough of them, and they’re looking at their CS team wondering if they can bridge the gap. Usually, they can’t. Here’s why —...
by Jason Lemkin | May 24, 2026 | Blog Posts, The Agents
Amelia and I just recorded Episode 005 of The Agents right before 2026 SaaStr AI Annual. You may have missed it in all the fun of the big event, here’s your chance to catch up! Most importantly: we both got the cost number completely wrong for our AI Agents....
by Jason Lemkin | May 24, 2026 | Blog Posts, Early, Marketing, Marketing, Metrics, Q&A |
Dear SaaStr: As a Startup, What Are Some Effective Ways For an Underdog to Take Down Their Competition? It depends on the gap. In B2B historically, I’d argue if your competitor is larger than you, at $8M-$10M+ in ARR and growing quickly, with even reasonably...
by Jason Lemkin | May 23, 2026 | Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
Here’s the exact prompt I typed into Replit the other day “ok i have an idea where we built a new speaker card page, where if you upload a headshot, we build you a 1080×1080 card on a background you pick from (one is attached) and show your headshot...
by Jason Lemkin | May 23, 2026 | AI App of Week, Blog Posts
The Bottom Line: Alex Turnbull bootstrapped Groove from $0 to $5M ARR as a solo founder over a decade. Then he bet against his own playbook. Helply is the AI-native B2B support platform he’s building in public. The support platform itself is free forever. No...
