The 2.0 SaaStr.AI Is Here, and It’s Still FREE: The AI Co-Pilot Every B2B Founder Has Been Waiting For
After 139,156 conversations, millions of interactions, and feedback from thousands of founders across our community, we’ve rebuilt SaaStr.AI.
The new SaaStr.AI 2.0 can:
- Hone your sales pitch with real-time feedback trained on 1,000+ successful B2B pitches
- Review VP candidates together by analyzing resumes, interview notes, and cultural fit against proven scaling frameworks
- Test your financial model with scenario planning based on 20+ years of SaaS data
- Level up your VC pitch using insights from $50B+ in funding rounds we’ve tracked
- Create a sales comp plan that actually drives the behaviors you want (not the ones that destroy your margins)
- And so much more that we’re still discovering ourselves
Try it now at SaaStr.ai — because every minute you’re not using AI to scale your B2B company is a minute your competitors are pulling ahead.
Why It’s Great. And Why For B2B Founders & Execs — It’s Often Better Than ChatGPT
We could have just added some ChatGPT wrapper and called it “AI.” But if you are in B2B, what we’ve done is much better. You get everything from the LLMs … plus the accumulated wisdom of all of SaaStr, and all its content, speakers and more.
The Training Data That Makes it Epic
SaaStr.AI 2.0 is trained on 20,000,000 words of SaaStr content and 1,000+ of the best B2B leaders’ sessions. The depth and breadth of real founder problems we’ve ingested:
- Every pitch deck teardown from our events (the ones that raised $500M+, and the ones that didn’t)
- Real revenue data from 2,000+ SaaS companies at every stage from $0 to $1B+ ARR
- Actual hiring disasters and wins from hundreds of scaling conversations
- The comp plan math that works (and the 47 versions that don’t)
- VC feedback transcripts from 800+ VCs who’ve deployed $10B+ into B2B
This isn’t generic business advice. This is pattern recognition from the largest dataset of B2B scaling intel on the planet.
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It’s Free for SaaStr Community
We’ve put abuse limits in, but that’s it for now.
Our AI is now making product recommendations and many other things we never expected it would. When founders succeed using our AI, they remember where they got help. They come to SaaStr Annual. They invest in our portfolio companies. They become the speakers and mentors for the next generation.
Free isn’t a customer acquisition strategy. It’s an ecosystem investment strategy.
The Real Test: Does It Actually Work?
Numbers don’t lie. Since launching SaaStr.AI, we’ve seen:
- 34,000+ founder conversations in the first month alone
- 94% of users say it gave them actionable insights they couldn’t get elsewhere
- 67% return usage rate within 7 days (higher than most paid B2B tools)
- Average session length: 23 minutes (people don’t spend 23 minutes with bad AI)
But here’s what really validates the 2.0 approach: People are asking our AI about sensitive topics they’d never bring up with me or our team directly. Topics like “I’m thinking about quitting” or deeply personal founder struggles.
That’s not just product-market fit. That’s trust at scale.
The Use Cases That Surprised Us Most
We built SaaStr.AI 2.0 expecting founders to ask about fundraising and scaling. And they do. But the breakout use cases have been completely different:
1. The “Digital Co-Founder” Phenomenon
One of our fastest-growing portfolio companies had all board members and investors provide feedback on their investment memo – and the AI won.
We’re seeing founders literally bring “Digital Jason” into board meetings, strategy sessions, and crucial hiring decisions. Not as a replacement for human judgment, but as the voice that remembers everything we’ve learned about what works and what doesn’t.
2. Sales Pitch Surgery in Real-Time
Upload your pitch deck, paste your email outreach, or just describe your value prop, and SaaStr.AI 2.0 doesn’t just give you generic feedback. It shows you:
- Exactly where similar companies failed in their positioning
- The specific language that closed deals at your stage and industry
- Competitive differentiation angles you haven’t considered
- Pricing psychology mistakes that kill conversion rates
3. VP Candidate Evaluation That Actually Predicts Success
This one blew our minds. Founders are uploading entire candidate profiles — resumes, interview notes, reference calls — and asking SaaStr.AI to evaluate cultural and competency fit.
The AI doesn’t just check boxes. It pattern-matches against the leadership transitions we’ve documented across thousands of scaling companies. It flags the subtle red flags that human intuition misses and highlights the unconventional strengths that could be game-changers.
The Technical Architecture That Makes This Possible
Here’s what makes SaaStr.AI 2.0 fundamentally different:
Context That Compounds
Every conversation makes every future conversation better — not just for that user, but for every founder in our community. When someone asks about Series A positioning, the AI learns from every similar conversation that’s happened before, while maintaining complete privacy.
Real-Time Learning That Actually Works
When I see a mistake (e.g., the AI got the dates wrong for SaaStr Europa 2025, which is probably because we haven’t launched yet so it’s “guessing”), I just make a quick voice note and the model is almost instantly updated. And the hallucination goes away.
This isn’t theoretical. The AI gets better every single day based on real founder feedback.
Multi-Modal Input Processing
Upload documents, paste links, describe verbal conversations, share spreadsheets — SaaStr.AI 2.0 processes it all and gives you synthesis that considers every data point simultaneously.
What Every B2B Founder Should Do Right Now
Stop reading this post and go try SaaStr.AI 2.0. Seriously.
But when you do, don’t just ask generic questions. Here are the prompts that are generating the most breakthrough insights:
For Sales Leaders:
“Here’s our current sales pitch deck [upload]. We’re converting 12% of qualified demos to closed deals. Show me exactly what’s broken and how to fix it, based on companies that have solved similar conversion problems.”
For Fundraising Founders:
“I’m raising a Series A in Q2. Here’s our deck [upload], our financial model [upload], and our competitive landscape [paste]. What are the 3 biggest objections VCs will have, and what’s the specific evidence I need to overcome each one?”
For Scaling CEOs:
“I need to hire my first VP of Sales. Here’s our current revenue trajectory [describe], our product complexity [explain], and our target market [detail]. What profile should I hire, how much should I pay them, and what are the red flags I should watch for?”
For Product Strategy:
“We’re debating our roadmap priorities for 2025. Here’s what customers are asking for [list], here’s our technical constraints [explain], and here’s our competitive pressure [describe]. Help me sequence this roadmap for maximum business impact.”
It’s Your S-Tier SaaS Mentor
Think about this for your app, if you haven’t gone all-in on AI. What if your competitor can handle millions of interactions effortlessly a month? Automate almost all those workflows that today aren’t automated?
SaaStr.AI 2.0 isn’t just a tool for founders to use. It’s a proof point for what every B2B company should be building.
We’re a 5-person team that now handles more founder conversations than teams 100x our size. Before AI, we maybe could respond to a handful of email-based issues, and a few chats. And we could not provide any direct 1-on-1 advice.
Now? We’re providing personalized scaling advice to thousands of founders simultaneously, with quality that often exceeds what they’d get in a $500/hour consulting session.
If we can do this with community content and event recordings, imagine what you can do with your actual product data, customer interactions, and domain expertise.
The Competitive Implications Nobody’s Talking About
Here’s what keeps me up at night (in a good way): We’ve democratized access to world-class B2B scaling knowledge.
A first-time founder in Mumbai now has the same access to proven B2B frameworks as a serial entrepreneur with 20 years of Silicon Valley networks. A bootstrapped company in Ohio can test their pricing strategy against the same data that billion-dollar unicorns use.
This levels the playing field in unprecedented ways. Geographic advantages diminish. Network effects become less crucial. What matters is execution speed and the willingness to learn from the accumulated wisdom of the entire B2B ecosystem.
But here’s the flip side: If everyone has access to best practices, the competition for exceptional execution intensifies dramatically. The founders who combine AI-assisted insights with world-class execution will pull away from the pack faster than ever before.
AI Isn’t Coming. It’s Here.
The AI revolution isn’t coming. It’s already reshaping how the smartest founders operate.
The question isn’t whether AI will transform B2B. The question is whether you’ll be leading that transformation or scrambling to catch up.
SaaStr.AI 2.0 is free, it’s live, and it’s waiting for you to test its limits.
Go break it. Push it harder than you think it can handle. Ask it the questions that keep you awake at 3 AM. Upload the documents you’re afraid to show investors. Test the strategies you’re not sure will work.
Because every minute you spend learning what’s possible is a minute you’re ahead of every founder who’s still waiting for someone else to figure this out.
Try SaaStr.AI 2.0 at SaaStr.ai
And when it helps you close that deal, nail that hire, or fix that broken process, remember: This is just the beginning.
The future of B2B belongs to founders who learn fastest. AI just made learning exponentially faster.
P.S. — We’re hosting SaaStr AI London December 2-3 and SaaStr Annual + AI Summit May 12-14, 2026. Come see what the future of B2B looks like when 10,000+ founders, executives, and investors gather to figure it out together. Early bird pricing ends soon.
