The Hidden Risk of Single-Developer Dependency in SaaS Companies
There’s a risk I see over and over again in SaaS companies — especially founder-led ones — and it’s rarely talked about openly until it becomes a real problem.
ElevenLabs Just Hit $330M ARR in 24 Months. It Took Twilio 8 Years to Get There.
ElevenLabs will probably be worth more than Twilio by mid-2026 Really seems like a missed opportunity there — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) January 13, 2026 ElevenLabs is on track to match Twilio’s market cap in under 5 years from founding....
SaasRise Enterprise Mastermind Call Recap Jan 13, 2026
This is what we discussed today in the Enterprise SaaS CEO and Founder Mastermind
The Most In-Demand AI Services Businesses Will Pay For in 2026
The fastest-growing AI opportunities in 2026 are not tools or apps. They are service businesses that use AI to save time, generate revenue, and reduce risk for buyers with real budgets. The post The Most In-Demand AI Services Businesses Will Pay...
![Eleven Steps to the Epiphany[^1]](https://res.cloudinary.com/dzawgnnlr/image/upload/w8txbopuyfkpsbw6rwka)
Eleven Steps to the Epiphany[^1]
I asked Claude Cowork to read my tools folder. Eleven steps later, it understood how I work. Over the past year, I built a personal operating system inside Claude Code : scripts to send email, update our CRM, research startups, draft...
If You’re Going to Stick with a Mediocre VP for Now, You At Least Have to Micromanage Them
I know this is advice you probably don’t want to hear. We’ve all been told that micromanagement is bad. That great leaders hire great people and get out of their way. That autonomy is the secret to building high-performing teams....
Open APIs Are Over
Salesforce, Datadog & Epic are building walls. After two decades of flourishing through open APIs & data portability, the software industry’s largest incumbents are locking down. Salesforce restricted Slack’s API1 in May 2025, limiting third-party apps to one API call per...
How to Use AI to Design Ads (ChatGPT, Arcads, Omagic, & AdCreative)
If you’d asked me ten years ago what it takes to design good ads, I would’ve told you to hire a graphic designer, brief them carefully, wait a week, revise three times, and hope it worked. That world is gone.
How to See Your Competitors' Ads with Meta Ads Library, Google Ads Library, and LinkedIn Ads Library
One of the biggest advantages B2B SaaS founders have today is transparency.Ten years ago, if a competitor was running ads, you had to guess. You might notice something scroll by in your feed, maybe screenshot it, and try to reverse-engineer...
How to Structure Your Digital Ad Campaigns (Campaigns, Ad Sets, & Ads)
One of the biggest mistakes I see SaaS founders make with paid ads isn’t bad creative or weak copy. It’s messy structure.
The Change You Need Is the Change You Make. SaaStr AI Annual 2026 Will Help You Get There.
Here’s what I’ve learned after 13 years of building SaaStr, investing in 50+ leading B2B companies, and watching thousands of founders navigate moments of massive disruption: The founders who win aren’t the ones who figure it out alone. They’re the...
Trajectory
In 2012, we cared that we used software. Today we care how we use it. The difference is trajectory. In the last decade, adopting software was the priority. Moving from on-premise to the cloud or digitizing a manual workflow promised productivity gains....
Where Agency Revenue Is Heading: Fewer Big Retainers, More Mid-Market Retainers, and Longer Engagements
Recently, Rand and I released the results of the State of Digital Agencies survey for 2025. Our goal of this annual survey is simple – get a temperate check on the digital agency world and give folks a benchmark for...
Beeper & Day One
Pankil Shah writes I replaced WhatsApp, Telegram, and Messenger with this one app. (It’s Beeper.) And Wirecutter picks the 3 best journaling apps of 2026. (It’s Day One.)
How to Get Dangerously Good at AI in 99 Seconds With Better Prompts
Most people get weak results from AI because they ask weak questions. This article explains a simple, repeatable prompting system that turns AI into real leverage while keeping human judgment at the center. The post How to Get Dangerously Good at...
5 Interesting Learnings From Motive at $500,000,000 ARR. And The Match Up With Samsara.
Motive filed its S-1 to IPO, and now we can finally see the real numbers behind one of the fastest-growing fleet management companies ever built. And with somewhat direct competitor Samsara trading at a ~$20B market cap and just hitting...
SaasRise Enterprise Mastermind Call Recap Jan 6, 2026
This is what we discussed today in the Enterprise SaaS CEO and Founder Mastermind
%20(1).png)
The Path to a Successful $100M+ SaaS Exit
Most SaaS founders say they want a big exit. Very few actually build their company in a way that makes a $100M+ outcome inevitable. That’s not because they lack ambition. It’s because they misunderstand what drives large SaaS exits in...
How to Keep Customers Without Lowering Your Prices: A 7-Step Retention System
Lowering prices does not stop churn. This seven-step retention system shows how to keep customers longer by accelerating value, reducing confusion, and increasing product adoption without discounting. The post How to Keep Customers Without Lowering Your Prices: A 7-Step Retention System...
This Week in SaaS - Dec 22, 2025 - Jan 5, 2026
The top M&A deals, venture deals, news, and blog posts of the week
Hooray, You Got Profitable. That’s Great, But It’s Not Enough. It’s Time To Reaccelerate Growth.
You did the easiest hard thing. You cut the burn the last 6, 12, 24 months. You right-sized the team. You got to profitability—or at least cash-flow positive. You survived when so many others didn’t. And that matters. A lot....
How Much Equity to Give Your First Employees: The Real Data From 50,000 Startups
One of the most common questions I get from seed-stage founders: “How much equity should I give my first hires?” It’s a high-stakes decision. Give too little and you can’t attract talent. Give too much and you’ll regret it by...
OpenAI’s GTM Lead Maggie Hott: No Commissions, 100% Pilot Win Rates, and the Race Against Incumbents
Most of what you hear about sales hiring is recycled advice: look for humility, avoid blamers, hire for grit. Fine. True. Not interesting. But buried in a recent conversation with Harry Stebbings and Maggie Hott — OpenAI’s GTM leader who...
Gross Profit per Token
Meta is acquiring Manus for $2 billion.1 Alongside the announcement, Manus disclosed $100 million in ARR achieved in eight months, 147 trillion tokens processed since launch.2 Can we use those figures to explain the acquisition price? Publicly traded software companies have gross...
This Week on How I AI: How Webflow’s CPO Built an AI Chief of Staff
Your weekly listens from How I AI, part of the Lenny's Podcast Network
One Reason The Best AI B2B Startups Are Growing So Quickly: Truly Insane Value
We talk a lot about what’s driving the fastest-growing AI startups. Is it the technology? The timing? The TAM expansion? Sure, all of that matters. But I want to talk about something simpler. Something that’s easy to overlook because it’s...
Dear SaaStr: My Co-Founder Is Threatening to Quit Unless I Give Him More Equity
Dear SaaStr: My Co-Founder is Threatening to Quit Unless I Give Him More Equity; what should I do? Generally, this is the last, best chance to fix things. Founder equity splits are a tough thing. What seems fair on Day...
AI And The Death of The 2021 Sales Process
The classic sales plays do still work. Hard work, knowing the product cold, showing up. But the classic 2021 playbook? It’s close to dead in the Age of AI. And here’s one example of why. The other day I did...
4 AI Automations Behind Million Dollar Businesses With No New Hires
Modern founders are no longer scaling by adding headcount. They are scaling by installing AI automations across sales, qualification, delivery, and finance to remove bottlenecks and unlock compounding growth. The post 4 AI Automations Behind Million Dollar Businesses With No New...
This Week on How I AI: How to Get Your Whole Team Excited About AI
Your weekly listens from How I AI, part of the Lenny's Podcast Network
Dear SaaStr: When Should You Sell Your Startup?
Dear SaaStr: When Should You Sell Your Startup? Having been through the acquisition process 4x — twice as a founder, twice as a start-up exec, here’s my list of when and if to sell. Don’t take it literally. Most startups...
App of the Week: OpenRouter — The Universal API for All Your LLMs
One API. 300+ Models. 60+ Providers. And Why Every AI-Native Startup Needs This. We’ve featured a lot of amazing AI tools in our App of the Week series. But OpenRouter might be the most foundational one yet. Because if you’re...
🧠 Community Wisdom: What PMs Need to Master in the Age of AI, Testing Product Activation with AI Browsers, Splitting Time Between PM Work and Prompt Engineering, Mixpanel Vs. PostHog, and More
Community Wisdom 166
.png)
B2B Digital Ads Strategy: Meta, Bing, Google, and LinkedIn
For most B2B companies, paid advertising feels frustratingly inconsistent. One month it looks promising. The next month it feels expensive, noisy, and impossible to scale. As a result, many teams either give up too early or over-commit to a single...
.png)
How to Set up Third Party Ad Tracking with Cometly
As B2B marketing becomes more complex, attribution becomes harder—not easier. Buyers move across channels, devices, and platforms over weeks or months before they ever convert. Yet most ad platforms still try to assign credit in isolation, as if they were...
Is Zendesk Building a Glean Competitor with Its Unleash Acquisition? Not Exactly, But Here’s What’s Really Happening
Zendesk just announced the acquisition of Unleash, an Israeli AI-powered enterprise search startup with 70+ connectors to things like Google Drive, Confluence, and SharePoint. The pitch is “permission-based RAG” and AI agents that live inside Slack and Microsoft Teams. Sound...
Wolfram Automattica
It’s exciting to announce that Stephen Wolfram has joined as a special advisor to Automattic. I promise this is not just because he is such an incredible blogger, using WordPress, natch. If you don’t know about Stephen Wolfram, his about...
Databricks Vs. Snowflake at $5B ARR: Same Revenue, 2x Valuation Gap. Here’s Why.
Two Giants, Same Revenue, Completely Different Trajectories This is one of those moments in enterprise software history worth pausing on. Databricks and Snowflake — the two companies that have defined the modern data stack — are now both at just...
The Best Growth Tactics of 2025
50+ things that actually worked, as submitted by readers
The $7,500 Migration Fee That Just Cost a Vendor $80,000 ARR. Really, $240,000.
I almost switched vendors today. After many, many years with our current solution, I was ready to make the jump. New vendor lined up. Budget approved. $80,000 a year contract ready to sign. Then I saw it: $7,500 migration fee....
Klaviyo Adds Co-CEO To Get Back To Product. The Dream, But Does It Work?
So Andrew Bialecki, co-founder and CEO of Klaviyo, just made the announcement every technical founder dreams about: He’s bringing in Chano Fernandez (the ex co-CEO of Workday) as co-CEO so he can go back to product. Chano will run GTM,...
Cloudflare CMS Stats
Cloudflare released their Radar report for 2025, one fun stat was they analyzed the top 5,000 domains, and it had some interesting results for website technologies. Open Source tech came in at 47% for WordPress and 4.7% for Drupal, which...
The Bifurcation in the AI Market
Despite open-source AI models being 10-100x cheaper, proprietary providers haven’t lost pricing power. OpenRouter’s data reveals a market splitting in two. Over the last year, open-source models’ market share has remained stable around 22-25%, briefly spiking to 35% during the explosive...
SaaStr AI App of the Week: Kintsugi — The AI That Puts Sales Tax on Autopilot
Every week, we highlight an AI-powered app that’s actually solving real problems for B2B and Cloud companies. This week: Kintsugi. The next generation AI agent for B2B tax compliance. The Problem Nobody Wants to Talk About One dirty little secret...
The First $100,000,000 ARR at Samsara: How Founder CEO Sanjit Biswas Built a Platform Giant by Digitizing the Physical World
Samsara is one of the most successful vertical SaaS companies of all time. They’ve just crossed a stunning $1.75 Billion in ARR — growing 29%. That’s about as good as it gets, folks. CEO Sanjit Biswas, the co-founder and CEO...
SaasRise Mastermind Recap - Dec 10, 2025
The SaasRise Mastermind meeting on December 10, 2025, featured discussions among SaaS CEOs and founders on these topics.
55% of All Departmental AI Spend Is Now on Coding. And It’s Not Slowing Down
So why are we talking so much about Cursor, Claude Code, etc? Well for a good reason. Not only did both rocket to $1B ARR in less than one year, no it’s more than that. Coding is 55% of all...
Want to Get In Front of 3,500 B2B + AI Buyers a Week? Submit Your AI Agent to SaaStr
So we quietly launched something last week that’s taken off faster than we expected. The SaaStr AI Agents Directory. It’s now getting 3,500 visitors a week — and these aren’t tire-kickers. These are B2B founders, revenue leaders, and ops teams...
Dries OSS
A more accurate framing would be that Fizzy is source available. You can read it, run it, and modify it. But DHH’s company is keeping the SaaS rights because they want to be able to build a sustainable business. That is...
The Two Context Databases Powering Enterprise AI
Enterprises learned a lesson from cloud data warehouses. They handed over both data & compute, then watched as the most strategic asset in their business, how they operate, became someone else’s leverage, which created an opportunity for Iceberg. Fool me once… Leaders...