#21 GTM Growing Pains, AI Subscriptions, and the Next SaaS Transformation
March 27th, 2025
Insights, real stories and food for thought about “healthy” SaaS and AI agent go-to-market strategies, customer-centric growth and efficient recurring revenue models in both Tech and Traditional Industries.
Manually curated by Luigi Mallardo.
GTM Growing Pains at 10M+ ARR: Lessons from Cloud Academy
In the last edition, I shared an article about a typical Enterprise SaaS GTM struggle. What happens when growth slows between $5M and $15M ARR and how to fix it. A few CEOs I know thought I was talking about their company… interesting.
This time, I’m sharing another real-world case—Cloud Academy—one I have worked with.
Even profitable scale-ups surpassing $10M ARR with strong 50% YoY growth can hit GTM walls that make scaling to $20M–$30M much harder. Cloud Academy’s story is full of insights for companies in similar situations. How do you spot these issues early? What course corrections actually work?
The AI Wave Keeps Accelerating
The last time I felt this level of excitement about market shifts was back in 2010–2012, when I was learning how SaaS was changing GTM forever. AI is having a similar and even more powerful moment.
Here are some key moves I’ve been watching in the last few months:
SaaSing-up
Sam Altman’s Vision for AI Subscriptions
“Currently, I am more excited to figure out how we can charge people a lot of money for a really great automated software engineer or other kind of agent than I am making some number of dimes with an advertising-based model.” Link.
AI Getting Into Telco Bundles
Singapore telco Singtel is bundling Perplexity Pro as a free add-on. Just like Spotify or Netflix. Found this in Benedict Evans’ newsletter, and it caught my eye. Link.
YouTube Launches a $7.99 Subscription
YouTube, the goliath of online video, is now Netflix’s biggest rival for attention. Link.
SaaS Market Moves
Is Deflation Coming to SaaS?
Suddenly, those old pricing models look outdated and heavy. Let’s talk about the elephant in the room. Link.
SaaS Resilience: 2024 KeyBanc Report
Growth may be slowing, but SaaS remains strong. Key insights from the latest KeyBanc Capital Markets report. Link.
Microsoft vs. Adobe: AI Pricing Smoke & Mirrors
Microsoft’s Copilot pushes an extra charge on subscriptions. Adobe plays a different game. Are we paying for real AI breakthroughs or just their profit margins? Cut the crap and demand real value. Dig here.
AI, Agents as a Service & Robots
OpenAI Explores ‘Salaries’ for AI Agents
Call it ‘salaries’ or ‘subscription fees’. it’s still SaaS. Link.
Global Robot Density in Factories Doubled in 7 Years
We’ve gone from 74 robots per 10,000 employees in 2016 to 162 in 2023. Link.
Klarna’s AI-First Transformation
Klarna made waves last year by replacing SaaS vendors with ChatGPT. Now, they’ve cut 20% of their workforce, largely through attrition. Peers remain skeptical. Link.
Klarna CEO recently clarified their perspective. Linkedin post.
ChatGPT Subscribers Nearly Tripled to 15.5 Million in 2024. Link.
Grok3 vs. ChatGPT: Who Wins the SaaS Battle?
Grok3 is setting new performance records, but will users actually switch from ChatGPT? With 300M users already integrated, OpenAI holds the advantage. Unless Grok proves overwhelmingly better. Link.
By the way I’m using Grok and I’m starting to really like it.
Microsoft’s Copilot mess here.
Everyone Is Building AI Agents—But No One Agrees on What They Are. Link.
Interesting reads
Europe’s Cloud Shift
European firms and agencies are eyeing a switch from US cloud giants to local providers, fearing data privacy risks under Trump. Concerns over security and sovereignty are driving the shift. Link.
AI Hype & Bull Festivals
Scientists found that large crowds don’t move randomly but flow like a vortex. Isn’t this what is happening to the AI Hype? Link.
That’s all for this edition. What’s your take? Let’s discuss. Reply or DM me.