AI Surprises: From Chatbot to Product Guru

SaaStr's AI assistant, initially designed for basic support, has taken on unexpected roles. In just five weeks, it has conducted over 30,000 conversations with B2B executives, offering insights beyond its original scope.

Notably, the AI has:

• Reviewed hundreds of VC pitch decks and board packages

• Drafted compensation plans for sales leaders

• Rewritten outbound sales scripts

• Coached founders through business slowdowns

• Evaluated candidates and advised on hiring decisions

• Assessed speaker submissions for SaaStr events(SaaStr)

Perhaps most impressively, it has begun making unsolicited product recommendations, such as comparing tools like Clay and Apollo, despite not being programmed for this function.(SaaStr)

This evolution underscores a key insight:

“A great AI can do many things. Perhaps especially, do things you never expected it to do.”

The takeaway for sales professionals? AI's capabilities are expanding rapidly, often in unforeseen ways. Embracing these developments can unlock new efficiencies and insights in the sales process.

Reference: Lemkin, J. (2025, April 24). Our AI is Now Making Product Recommendations. And Many Other Things We Never Expected It Would. SaaStr.

From Zero to Unicorn: The Codeium Playbook

In just under a year, Codeium skyrocketed from a three-person sales team to a $1B+ AI powerhouse. Their secret? A blend of founder-led sales, strategic hiring, and a culture that rewards performance.

Graham Moreno, VP of Worldwide Sales, shared in SaaStr’s CRO Confidential:

“Before hiring their first sales reps, the founders personally closed millions in revenue.”

This hands-on approach laid a solid foundation for scaling. By bringing in proven talent from companies like MongoDB and Snowflake, they ensured a high-performing, culturally aligned team. Their compensation models? So effective that 70% of early hires exceeded annual quotas, with some on track for seven-figure earnings.

Codeium’s AI assistant isn’t just a tool—it’s transformative. Generating 45% of developers’ code, it’s turning weeks of work into hours. And by investing early in RevOps and enablement, they built a scalable, data-driven sales machine.

Reference: Lemkin, J. (2025, March 5). CRO Confidential: How Codeium Built A Billion-Dollar AI Company and a Winning Sales Machine with VP of Worldwide Sales, Graham Moreno. SaaStr.

Smarter Than 90% of Your Team

Here’s a bold claim: AI can’t sell (yet), but it’s already smarter than most of your sales team.

That’s the take from SaaStr’s Jason Lemkin—and it’s not just hype. Today’s AI knows your product better than your average rep, never forgets a detail, and can instantly pull from a knowledge base of millions of data points.

Here’s the line that really stings (or inspires):

“It probably already knows your product better than 90% of your sales team.”

What does that mean for sales leaders? You can’t afford to ignore the gap. The reps who treat AI as a threat will get left behind. The ones who treat it as a coach, assistant, and strategic partner will thrive.

AI might not close the deal today, but it’s setting the table, running the playbook, and prepping every rep to perform better—if they’re willing to lean in.

Want to stay valuable? Make sure you're doing what AI can’t—building trust, adapting on the fly, and influencing decisions. The rest? Let the machines handle it.

Reference: Lemkin, J. (2025, April 15). AI Can’t Sell (Yet) — But It’s Probably Already Smarter Than 90% of Your Sales Team. SaaStr.

AI Is Disrupting B2B Startups

AI isn't just a buzzword—it's reshaping the B2B SaaS landscape. Traditional startups face mounting challenges as AI becomes integral to product offerings.

Jason Lemkin outlines six reasons why AI poses a threat to conventional B2B startups:

1. AI as a Baseline: Customers now expect AI capabilities as standard. Without them, products seem outdated.

2. Increased Competition: AI tools have lowered entry barriers, leading to a surge of new competitors.

3. Elevated Customer Expectations: Users demand smarter, faster, and more automated solutions.

4. Pricing Pressures: AI-driven efficiencies are pushing prices down, challenging traditional pricing models.

5. Feature Parity: Even basic AI features can sway customer decisions, making it essential to keep up.

6. Innovation Acceleration: AI is fueling rapid innovation, and startups must adapt quickly to stay relevant.

The message is clear: integrating AI isn't optional—it's imperative for survival and growth in the evolving B2B SaaS market.

Reference: Lemkin, J. (2025, April 13). 6 Practical Reasons AI is a Threat to Traditional B2B Startups Today. SaaStr.

AI Will Join Your Sales Calls

If you think AI is coming someday, think again. It’s already here—and it’s stepping into your meetings.

According to Jason Lemkin, we’re just 12–18 months away from AI attending every sales call. Not just listening in—but actively contributing, answering questions, and eliminating those awkward “I’ll get back to you” moments.

Here’s the quote that hits hard:

“AI will join your sales calls – Within 12–18 months, your AI will be on every call, knowing your product cold and eliminating ‘I’ll get back to you’ moments.”

But that’s just one part of the shift. AI is also expected to handle up to 50% of all low-value sales—especially deals under $10K. That frees you up to focus on the bigger stuff: strategic selling, deeper discovery, and building real trust.

AI isn’t here to replace top salespeople. It’s here to empower them. If you can adapt and embrace the tools, you’ll move faster, close more, and stay miles ahead of reps stuck in manual mode.

The message is clear: start working with AI now—or risk being left behind.

Reference: Lemkin, J. (2025, April 28). 10 Ways AI Will Change Sales Forever. It’s Already Happening, In Fact. SaaStr.

Otter.ai’s $1B Sales-Free Growth Hack

Imagine building a billion-dollar SaaS empire without a single sales rep. Otter.ai did just that.

Their secret? A bold, bottom-up strategy powered by AI, virality, and a freemium model that felt almost too generous.

Here’s the standout insight:

“In AI SaaS, your free tier should be uncomfortably generous if you want rapid bottom-up adoption.”

Otter offered 600 free minutes of transcription—while competitors charged $1 per minute. That’s not just generous; it’s strategic. By owning their AI infrastructure, they made this model sustainable.

But they didn’t stop there. By encouraging sign-ups with work emails and calendar integrations, Otter unlocked a goldmine of enterprise data. This allowed them to map usage patterns, identify decision-makers, and target enterprises effectively—without a traditional sales team.

Every meeting became a growth engine. Shared notes introduced new users, who then brought Otter to their own meetings, creating a viral loop that fueled exponential growth.

The takeaway? In the AI era, building a product that sells itself isn’t just possible—it might be the smartest play in the book.

Reference: Lemkin, J. (2025, March 25). From 0 to 1 Billion Meetings: How Otter.ai Built a Bottom-Up AI SaaS Without a Single Sales Rep. SaaStr.

Small AI Startups, Big Scaling Problems

“Small but mighty” AI startups are making waves—some even hitting $20M to $100M in ARR with lean teams. But as Jason Lemkin points out, this model has a hidden flaw: it often doesn't scale.

These startups thrive on early momentum, but when it comes time to expand, they face significant challenges. The very lean structures that propelled their initial success can become obstacles, making it difficult to build robust sales, marketing, and customer success teams.

The key takeaway? Early efficiency is impressive, but without a plan for scaling operations and teams, even the most promising AI startups can hit a growth ceiling.

Reference: Lemkin, J. (2025, April 8). The Problem with “Small But Mighty” AI Start-Ups. SaaStr.

Salesforce's Bold Bet on AI and Sales

In a surprising move, Salesforce announced that in 2025, it will hire zero new engineers, citing a 30% productivity boost from AI. Instead, the company plans to expand its sales team by 20% to capitalize on the growing demand for AI solutions.

CEO Marc Benioff emphasized the company's strategic shift:

“In 2025, they are hiring 0 new engineers. None. Because they think AI makes them 30% more productive; and In 2025, they’re expanding their sales team by up to 20%. Because they want to win in selling AI.”

This approach underscores Salesforce's commitment to leading the "Digital Labor Revolution" by focusing on deploying AI agents and enhancing enterprise sales efforts.

Reference: Lemkin, J. (2025, May 12). Salesforce: We Are Hiring 0 Engineers This Year. But We’re Growing The Sales Team +20%. Because AI. SaaStr.

AI Is Already Changing Sales

If you think AI is a future trend, think again. It's already transforming the sales landscape.

According to Jason Lemkin's article, "10 Ways AI Will Change Sales Forever. It’s Already Happening, In Fact," AI is poised to revolutionize B2B sales within the next 12–18 months. One of the most compelling insights from the article is:

“AI will join your sales calls – Within 12–18 months, your AI will be on every call, knowing your product cold and eliminating ‘I’ll get back to you’ moments.”

This means that AI won't just assist with administrative tasks; it will actively participate in sales calls, providing real-time, accurate information, and enhancing the overall customer experience.

Furthermore, AI is expected to handle up to 50% of routine sales, especially for transactional deals under $10K. This shift will allow sales professionals to focus more on complex, high-value interactions that require human intuition and relationship-building skills.

The integration of AI into sales processes is not a distant future—it's happening now. Sales professionals who embrace AI tools will be better equipped to meet increasing customer expectations and stay ahead in a rapidly evolving market.

Reference: Lemkin, J. (2025, April 28). 10 Ways AI Will Change Sales Forever. It’s Already Happening, In Fact. SaaStr.

AI Is Already Remaking SaaS

AI is no longer a futuristic concept in the SaaS world—it's the present reality. As Jason Lemkin notes, "AI isn’t a differentiator anymore per se — it’s the baseline." Customers now expect AI capabilities to be seamlessly integrated into products, enhancing workflows, onboarding, and predictive insights.(SaaStr)

This shift has led to skyrocketing customer expectations. Users demand faster, smarter, and more automated experiences. Onboarding should be seamless, communications should be automated, and insights should be readily available. To meet these expectations, products must be significantly better than they were even a year ago.(SaaStr)

AI is also revitalizing freemium and product-led growth (PLG) models. With AI enhancing onboarding and initial usage, customers can quickly realize value, making PLG strategies more effective than ever.(SaaStr)

However, AI is also disrupting pricing structures. Software categories that rely heavily on manual processes are being challenged by AI-driven alternatives that offer faster and cheaper solutions. Companies that fail to leverage AI to improve efficiency may find themselves under pricing pressure.(SaaStr)

On the upside, AI is improving gross margins for SaaS companies. By effectively integrating AI, companies can deliver more value at a lower cost, gaining a competitive advantage. As Lemkin observes, "Gross margins will improve for AI-driven SaaS. Don’t let costs be an excuse."(SaaStr)

In summary, AI is fundamentally transforming the SaaS landscape. Companies that embrace AI and integrate it effectively into their products and strategies will be well-positioned to thrive in this new era.

Reference: Lemkin, J. (2025, March 24). AI is Already Remaking SaaS. 10 Trends To Watch Right Now. And Not Fall Behind On. SaaStr.