Monday.com has been a powerhouse in SaaS, scaling from $10M ARR in 2017 to over $1B — in just eight years (!)

Co-CEO and Co-Founder Eran Zinman recently sat down with SaaStr CEO and Founder Jason Lemkin to share his insights on their journey, including how they’ve leveraged AI, maintained growth, and expanded into multiple product lines.

Here are five AI learnings and 3 non-obvious business takeaways from the discussion.

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So in Salesforce’s most recent earnings report CEO Marc Benioff summarized a bunch of things they’ve been talking about for months.

• 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.  Because they want to own the AI war for the digital worker.

They’ve talked about both before, but I hadn’t seen them explicitly tied by Benioff and Salesforce before.

Is this really the right path? Or is it slightly disguised cost containment as they look to expand their profit margins further? Or is it both?

Benioff says their #1 goal today isn’t winning CRM or Data. No it’s “leading the Digital Labor Revolution.” Being the #1 in the enterprise in deploying agents and more.

So the 2021 GTM Playbook is Dead. Almost all of us agree on that.

That playbook was fueled by a desire to load up on 100s of new SaaS apps to fuel a pandemic-inspired buying spree. Today, SaaS and Cloud is back, and AI-fueled B2B spend is on fire.  But we’re not expanding the total number of apps customers pay for by all that much.  Our app count is staying flat. And competition has exploded. AI has ushered in 100s of new competitors in each category. And changed the game at the product level. Customers now expect so, so much more for their SaaS dollar.

So if the 2021 GTM playbook is dead, what has replaced it? Or will replace it?

It’s still murky.

The reality is, the 2025 GTM Playbook is mostly the 2021 one done much more aggressively, with more effort (not less), with better tools, but tools and AI alone are not the answer. Not yet at least.

What doesn’t work nearly as well today, but so many are still doing:

• Endless generic outbound emails. The hit rates here keep going down.
• Low energy digital “events”. No one comes anymore.
• Break-up emails. It’s not about you.
• 2021 SEO strategies. Still work, but in rapid decline in many cases.
• 2021 mass-scale content strategies (1000s of pages of content).  Google doesn’t like this anymore.
• Spending all day on LinkedIn.  No, for 95% of folks, this isn’t “social selling”.
• Most traditional press and most basic PR strategies.  Who reads to day?
• “Customer Success” teams that are just there to upsell and not help.  This might get you more revenue today. But it doesn’t fuel the word-of-mouth engine and create more new customers and leads.
• Endless price increases on the base.  This may help you hit the plan in the short term but again does not fuel word-of-mouth.  It certainly does not create new leads and customers.

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So Salesforce has now grown into the active granddad of SaaS.  Maybe not growing quite as fast as it once did.  But it’s matured into a true force of nature. Only Microsoft, Oracle and now Salesforce have crossed $40 Billion in enterprise software ARR.

• $40 Billion in ARR
• Growing 9%
• 33% Non-GAAP Operating Margins (19% GAAP)
• Generating $13B of free cash flow a year!!

Perhaps most importantly, Salesforce has leaned deeply into AI … and while the early usage is impressive, so far it hasn’t materially changed growth. So far:

• Since October, closed 5,000 Agentforce deals, including more than 3,000 paid just 90 days after officially launching.
• Salesforce says Agentforce has managed 380,000 conversations, with only 2% escalated to humans and an 84% resolution rate.

So far, at the public company level, it’s the infra players that are seeing the crazy AI growth. Nvidia, Google Cloud, Azure, etc. But how about 2026+?  We’ll see.  As Marc Benioff notes below, Salesforce’s just started.  It’s only been selling AgentForce for a few months. He’s incredibly excited and bullish on where it’s going. It’s clearly rejuvenated him. Maybe AI will for all of us.

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