The debate around if outbound still works, how well, and what AI’s role will be, I think a huge point is missed:

You’re wasting your shot.

Email remains special. Literally every executive manages their >own< inbox. Every day I open 20-30 cold emails. So do the CEOs and CXOs of almost every public company, almost every buyer, etc.

Almost everyone is thinking about email wrong. Are fewer, better emails better than spray and pray? Most of us now agree. But it’s more than that.

Any emails that gets opened by a buyer is a gift. It’s your shot, your audience.

Hey SaaStr Community,

As you're building and scaling a SaaS company, there’s only one place you have to be this year: SaaStr Annual 2025, May 13-15 in the Bay Area.

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Build and ship AI-native products

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Scale Smarter with AI—Join SaaStr Annual 2025. Save 20% before prices go up March 31st.

2025 is year that AI takes over all of support and customer success … that isn’t sales.

This is how the 2 related but different categories are segmenting out.

A lot of support is questions and problems from existing customers.  Almost all of this is going to AI, as much as possible. And this trend is accelerating. Many are already seeing 40% or more of tickets resolved by AI in Intercom, Zendesk, Gorgias, Dialpad, Talkdesk, etc. And some are pushing this much higher.

But, where support is really sales, humans will handle it still.  We’re already seeing this bifurcation in e-commerce, because there the “support” chat is often used for sales questions. Which shoes, which size, does this run large, etc. AI for returns, humans to convince you to buy. Etc.

The same is happening, just more slowly across customer success.

Humans are still deployed in customer success for upsell. To get you to buy more stuff. Directly, or in “QBRs” and similar which now have become mainly about upsell.

And the rest is being handed off to AI, support, etc. Or just being eliminated for now, to be replaced by AI soon.

So we’ve all watched the mega VC rounds for OpenAI, Databricks, Anthropic etc as VCs deploy billions into the AI winners at scale.

But just how much of venture capital overall is going to … the top names?

Far more than ever, per Redpoint’s latest data.

In 2024, 31% of all VC capital went into just 20 deals.  A record.

From 2020-2022, the top 20 deals were just 6%-8% of all VC capital.

Now there’s a lot going on here and part of the rush in 2024 and 2025 is that more capital is coming into VC again.

But it still shows where the energy and momentum are.  Massive investments, at massive valuations, into the biggest leaders of AI.

At a scale we haven’t seen before.

So many VCs I’ve known for years are all-in on massive checks to the break-out winners here.  It’s the game most, at least by dollars, are playing today.

GBGH is back — with vengeance — in venture capital.

This edition of the SaaStr Daily is sponsored in part by Prismatic

Unlock product growth with a solid integration strategy. Download our guide for info on tools, requirements, priorities and more.

So when growth slows, the conversations change.

You start to hear:

A ton of talk about raising prices. A lot. There are reasons to do this, but not because you are missing the plan.

Deleting low-end and free editions. To force users and customers to pay more.

Forcing customers to buy multi-year contracts. This hides churn, but really only defers it.  If smaller customers want to pay monthly and are happy, why force them otherwise?

Threatening to sue customers over autorenewals, nonpayment, etc. You’re really going to go sue a customer?

Hanging on to low performers. Because recruiting gets harder.  You start to hear a lot of excuses for underperforming management when growth slows.

Moving customer success into sales. But then who will care about the customers, really?

The founders may be the only ones to fight here.  That energy has to go into winning, into gaining market share, into getting back to growth.  Not into getting more pain out of the base.

So Dropbox was the fastest B2B app of the last era to rocket to $1 Billion in ARR.  It seemed crazy at the time, and even in the age of OpenAI and Wiz, it still seems a bit crazy today.

Since then, it has IPO’d and transitioned to a new mature phase, where it’s highly profitable and focused on efficient scaling.  And now it’s transitioning to its third phase, investing big in its more AI focused business offering, Dash, while managing its classic but mature file sharing business efficiently.

Phase 3 of Dropbox:  “We are evolving from traditional file sync and share to AI-powered universal search and content intelligence.”

Drew Houston has been CEO since Day 1 in 2008 and we’re super excited to have him speaking at 2025 SaaStr Annual, May 13-15 in SF Bay!

So Pitchbook has some new data out on how much M&A of VC-backed start-ups … is by other VC-backed start-ups.

And it’s a record: 33.7% of all VC-backed start-ups that are acquired are by VC-backed buyers. Up from 20% in 2018. 

Now this isn’t necessarily bad:

• First, it’s not new.  20% of deals even in 2018 were start-ups buying start-ups.
• And the dollar value has gone up, it’s doubled since 2018, although down from a 2023 peak.
• And start-ups have gotten bigger.  So they can pay more..  Stripe, Databricks, etc. have done $1B+ acquisitions before their IPO.
• Sometimes, it gives you a chance to double down.  Get bought for stock early by Coinbase or Snowflake, sometimes the value can grow dramatically after the acquisition. Sometimes.

But a lot of these deals may be sort of “better than nothing” deals.  Better than shutting down. Better than running out of money. And they often are better than that.

Either way, a lot of this is start-ups looking for an exit … finding it at another start-up.

So if nothing else, build those relationships too. Not just with the big public Cloud companies.

This edition of the SaaStr Weekly is sponsored in part by Stripe

We've partnered with Stripe to give you access to the internet economy conference. Stripe Sessions brings together the payments and financial technology community to share ideas that drive progress.

So enterprise Cloud security leader Zscaler has its latest theats report out, and by the sheer nature of its scale in the enterprise, it has a massive dataset on just what apps are being used how in the enterprise.

The big take-aways:

• AI/ML transactions up 36x over past 12 months (!) or 3,464.6% :). (I know those don’t quite tie).
• ChatGPT is 45.2% of all transactions, but also the most blocked
• Grammarly is #2 in the enterprise. I knew it was popular, but I didn’t know it was that popular.

The Top 3 categories of AI apps in the enterprise are Productivity (ChatGPT, MSFT Copilot), Writing (Grammarly et al), and Language Translation (DeepL).

Join SaaStr CEO and Founder Jason Lemkin and Chris Dean from Treasury Prime as they delve into the intricate world of Banking as a Service (BaaS) and FinTech. The discussion spans a host of critical topics, including the fallout from Silicon Valley Bank, the complexities of reconciliation, Synapse and Evolve's banking controversy, and the evolving financial landscape.

They also explore the resurgence of FinTech, the impact of AI on banking operations, and Treasury Prime's upcoming AI-powered operational tools. A must-watch for anyone interested in the future of banking and financial technology. 

• SaaStr 795: The AI Impact on Banking and Finance with CEO and Co-founder at Treasury Prime, Chris Dean

• SaaStr 794: The Top 10 Customer Success Metrics Investors Care About in 2025 with Gainsight CEO Nick Mehta

• SaaStr 793: The 10-Point Checklist For When You Sell Your Company with David Frankel Managing Partner at Founder Collective and SaaStr CEO and Founder Jason Lemkin

Listen on Apple Podcast, Spotify or Google Podcasts

Every successful start-up had a Magical Sales Rep in the early days:

* often from a non-traditional background

* >really< got the product, + every use case

* knew how use the product to >truly< solve prospects' problems

* clever enough to work around big gaps

* part evangelist

A brutal truth of VC investing:

If you aren't 100% sure a founder is great ...they aren't great enough

And you won't make any real money

© SaaStr 2025

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