SaaStr

OCTOBER 27, 2024

Dear SaaStr: What Are Some of the Most Common Mistakes Entrepreneurs Make Pitching VCs? I’ve invested almost $200m as part of SaaStr Fund / 2024. A few top mistakes founders make: #1. Not making cold email truly great. Don’t ask to pick someone’s brain, or coffee. Make the cold email so great, you’d want to invest based on just it alone.

CTO 315

CTO Investment Revenue Marketing 315

SaaStr

NOVEMBER 30, 2024

Here’s an uncomfortable truth about SaaS companies: the majority of first-time VPs of Sales don’t make it past 12 months. As someone who has both succeeded and failed at making this critical hire, I can tell you that when it works, it’s transformative. When it doesn’t, it’s potentially catastrophic.

Sales Hiring 301

Sales Hiring Sales Recruiting Sales Headcount 301

SaaStr

DECEMBER 31, 2024

So I caught up the other day with the CTO of a leading SaaS company with tens of thousands of customers, growing quickly. AI is all over their homepage and website and comms. I asked him about a particular use case for AI, and his answer shocked me a bit: Honestly, our AI is basically still in beta.

AI 329

AI CTO Hire Sales Hiring CTO 329

SaaStr

NOVEMBER 13, 2024

So the latest SaaS leader to cross $1B ARR is Klaviyo. Klaviyo dominates marketing in the Shopify ecosystem and in ecommerce, and just keeps on scaling. It was the only SaaS IPO on 2023. The only one! And at almost $1B ARR, it’s still growing a stunning 34% (!). ” 5 Interesting Learnings: #1.

Scale 301

Scale SMB Scaling Enterprise 301

SaaStr

OCTOBER 25, 2024

When Marc Benioff started Salesforce, he codified the sales playbook. Then Mark Roberge , former Hubspot CRO, wrote The Sales Acceleration Formula with deep insights into quota structures. For the subsequent ten years in software, we’ve optimized every little bit of how we sell it.

Venture Capital 331

Venture Capital Marketing AI SaaS 331

SaaStr

DECEMBER 27, 2024

SaaStr CEO and Founder Jason Lemkin recently sat down with HubSpot Chairman and co-founder Brian Halligan , who shared valuable insights on the current state of SaaS, evolving board meeting formats, and how AI is reshaping the industry. Here are the key takeaways from part 1 of this interview.

AI 284

AI Marketing SaaS Interviewing 284

SaaStr

MAY 23, 2025

When SaaStr Fund made the first investment in RevenueCat back in 2018, nobody could have predicted that this “simple API for managing in-app subscriptions” would become the infrastructure powering 33% of all mobile subscription apps and reach a $500M valuation in 2025.

Payments 265

Payments Payment Solutions Underperforming Technical Team Payment Methods 265

SaaStr

JANUARY 8, 2025

So the overall “project management” space has seen widely disparate impacts from the SaaS partial downturn of 2022-2024. Asana, strong in B2B2B and selling to tech, was perhaps hit hardest, with growth slowing to 10%. Monday.com by contrast, selling mainly outside of tech, saw growth remain strong at 34%.

AI 301

AI B2B Scaling Trends 301

SaaStr

OCTOBER 31, 2024

What are the most common mistakes I see first time SaaS founders make? Second-time SaaS founders make other mistakes. They think they know more than they do. They spend too much. They often struggle to do things a new way. First-time founders have many positives. But they also make mistakes we tend not to make with experience.

Scale 307

Scale Social Media SaaS Business Model 307

SaaStr

DECEMBER 5, 2024

So it’s interesting how folks craft headlines from data. Carta release its latest funding data the other data for 2024 Year-To-Date here : What you can see is that large, hot AI later stage deals overall are indeed driving venture capital deployments up ~ +17% the year. But that’s for late-stage capital. Most of it AI driven.

Venture Capital 300

Venture Capital AI Data 300

SaaStr

OCTOBER 30, 2024

We’re obviously written up a lot about Fundraising and Investing here on SaaStr.com, but time and time again, SaaStr CEO and Founder Jason Lemkin has seen so many Founders sign a bad term sheet based on gut instinct, VC celebrity or vibes, and while that may be fine, it’s not enough.

Venture Capital 311

Venture Capital Software Review Investment Startup 311

SaaStr

JANUARY 3, 2025

The success rate for executive hires at high-growth SaaS companies can be surprisingly low – you’re often lucky if 50-60% of your management team works out long-term.

Sales Hiring 284

Sales Hiring Scale Systems Review Interviewing 284

SaaStr

JUNE 11, 2025

Dear SaaStr: How Does a Founder Mindset Change As You Go From Startup to Scaleup? The big changes I see: Moving (Over Time) From Hustler to Strategist. Though Stay a Hustler, Too 😉 In the early days, you’re in the trenches—selling, building, and doing whatever it takes to survive. But as you scale, you have to step back and focus on strategy.

Startup 263

Startup Interviewing Scaling Metrics 263

SaaStr

OCTOBER 23, 2024

In 2006, BILL CEO and Founder René Lacerte set out to define a category around financial operations for small and midsize businesses (SMBs). Needless to say, he succeeded. At SaaStr’s AI Summit during the SaaStr Annual , René chatted with SaaStr CEO and founder Jason Lemkin about how BILL has reached half a million customers and $1.3B

SMB 307

SMB Payment Services Payments Payment Methods 307

SaaStr

OCTOBER 18, 2024

SaaStr CEO Jason Lemkin joined ZoomInfo’s Season 2 of its ZI Labs Podcast as the opening guest alongside ZoomInfo CEO Henry Schuck. Along with co-host Ben Salzman, Jason and Henry discuss the transformative power of AI within SaaS and the evolving dynamics that are reshaping the landscape of software as a service.

Sales Recruiting 304

Sales Recruiting Sales Hiring Scale AI 304

SaaStr

OCTOBER 25, 2024

Dear SaaStr: How Much Should a SaaS Company Invest in Professional Services? A rough yardstick is that most enterprise-focused SaaS companies tend to get about 8%-10% of their revenues from professional services. A few data points: At $800m ARR, Qualtrics was still getting 25% of revenue from professional services.

Investment 297

Investment SaaS SMB Enterprise 297

SaaStr

OCTOBER 10, 2024

So Thomasz Tunguz put together a great chart summarizing one of my top worries over the past 24+ months in SaaS. He summarized the M&A (acquisitions) of The Top 10 Software Acquirers. And what you can see is there is really almost no liquidity for startups and scale-ups in SaaS and Cloud at the moment.

SaaS 309

SaaS Acquisition Cloud AI 309

SaaStr

DECEMBER 4, 2024

Pricing is more than just a number on a contract — when used thoughtfully, it can become a strategic tool for your SaaS product that can drive product adoption, customer satisfaction, and business growth.

Payments 284

Payments Pricing Scale Revenue 284

SaaStr

NOVEMBER 29, 2024

I know for many, this seems a much harder time to find a new job What I can tell you is this. It’s not the crazy hiring market of 2021.

Sales Hiring 284

Sales Hiring Scale Marketing SaaS 284

SaaStr

JANUARY 5, 2025

So does being a solo founder … work in SaaS? We’ve dug into this topic several times at SaaStr. Of the post ~40 SaaS IPOs, only 5 or so had solo co-founders. So let’s call that 10%-12% or so. Still, they are some good ones: Zoom, Scaler, New Relic, Elastic, etc.

Cloud 329

Cloud SaaS Data 329

SaaStr

DECEMBER 19, 2024

Salesforce, Nov 2024: We're hiring 1,000 new sales execs to sell AI!

Sales Hiring 306

Sales Hiring AI Headcount Sales 306

SaaStr

OCTOBER 26, 2024

Dear SaaStr: What’s It Like Being Beaten Up by Investors? It’s a gift, if you view it in the right context. First, don’t take it personally. Everyone that is smart can be tough critic. Everyone with a High IQ that’s been in tech a while can come up with 10-20 reasons why you will fail.

compliance 298

compliance Mobile Sales 298

SaaStr

JANUARY 12, 2025

So when Microsoft paid $26 Billion to buy LinkedIn, it seemed like they were getting a pretty good deal. Fast forward to today, it looks like a great one. LinkedIn is at $17 Billion in ARR, still growing 10%, and its whole division is wildly profitable with 50%+ operating margins! There may be better M&A deals in the history of B2B.

Acquisition 317

Acquisition B2B 317

SaaStr

DECEMBER 11, 2024

So one of the quiet SaaS leaders that has just crushed it in 2024 is Doximity: At $550m in ARR, it’s worth a cool $10.4 Billion (!) — or 20x ARR. And its stock it up a stunning +90% this year. What’s going on? A combination of: Growth re-accelerating. Doximity is growing 20% now, vs. 18% at $450m ARR. Insane profitability.

Business Model 274

Business Model SaaS Revenue Marketing 274

SaaStr

OCTOBER 16, 2024

So RingCental is both an incredibly impressive SaaS and Cloud company — but also a bit of a cautionary tale. It’s been around for decades but has continued to iterate, expanding into the enterprise, the contact center, and so much more. Fast forward to today, it’s at: $2.43 ARR Now they have $1.5

Scale 284

Scale Compensation SMB Cloud 284

SaaStr

DECEMBER 26, 2024

Gong has its 2025 State of Revenue out. You can grab it here. In general, the report ties to what were seeing everywhere in SaaS. Were ending the year in general with stronger growth that the prior year. Gong also looked across its entire customer base to measure deal velocity.

Scale 284

Scale Benchmarks B2B Enterprise 284

SaaStr

NOVEMBER 4, 2024

Dear SaaStr: What’s the #1 Reason You See Sales Reps Fail These Days? The #1 reason I see sales execs struggling today in new roles: they are convinced their playbook is better. And refuse to run the one that is already working. They are convinced they know better.

Sales Hiring 284

Sales Hiring Sales 284

SaaStr

DECEMBER 10, 2024

Dear SaaStr: What Was Your First Step When You Decided to Do a Startup? For me, both times, it was to find my co-founder. In my first start-up, arguably I invented the idea of the company , but my co-founder invented the technology. It was really all her. Step 1 was seeing if we wanted to do this crazy idea together.

Startup 272

Startup Technology Revenue Leadership 272

SaaStr

NOVEMBER 17, 2024

So the other day on Workshop Wednesday Andy Wilson, founder CEO of Logikull , and I did a deep dive on what it’s really like selling your company to Private Equity for almost $300,000,000!

Sales Hiring 293

Sales Hiring Banking Sales SaaS 293

SaaStr

JUNE 18, 2025

Dear SaaStr: Should I Hire a Sales Consultant as My First Sales Rep? No, you shouldn’t hire a sales consultant as your first sales rep. Here’s why: As the founder, you need to be the one to close the first 10–20 customers yourself.

Sales Hiring 228

Sales Hiring Consulting Scale Sales 228

SaaStr

OCTOBER 14, 2024

Dear SaaStr: What is The Strangest Thing You Have Learned About Entrepreneurship? To me the “strangest” thing I learned is that you get pretty good around Year 3–4. Almost automatically. And somewhere around Year 5 at least, if you make it that long — you know exactly what to do. I always had imposter syndrome as a CEO and founder — and still do.

Entrepreneurship 281

Entrepreneurship Revenue Management 281

SaaStr

OCTOBER 27, 2024

Top Posts: #1. The Bar Has Gone Up: The New Era of HyperFunctional SaaS with Jason Lemkin #2. 5 Pros, and 5 Cons, to Taking a VC Round at a Very High Valuation #3. Pitchbook: The Number of Active VCs is Down 62% From Its Peak. And Down Again in 2024. #4. Zuora Goes Private for $1.7 Why This is Good News for SaaS. #5.

AI 292

AI Cloud Startup SaaS 292

SaaStr

JANUARY 6, 2025

So some folks are going to disagree with me on this post, but I’m close to 100% right on it, and it will save you a ton of pain and time and money. Never hire someone who describes themselves as a “Strategist” unless that’s what you really, really want. Especially today.

Consulting 273

Consulting Strategy 273

SaaStr

NOVEMBER 14, 2024

Dear SaaStr: I Just Got My First SaaS Job 6 Months Ago and Now I Want to Quit. How Do I Tell My Boss? Almost everyone quits these days without giving a cr*p about the company: Zero notice. Instead, give 30 days if you can. No help finding a replacement. Instead, if you know someone else for the role, make the intro. No transition memo.

SaaS 284

SaaS Management 284

SaaStr

NOVEMBER 19, 2024

Most startup companies in earlier stages don’t have the most mature product. While differentiating your product against the competition is important, you have to differentiate yourself elsewhere as you build your company. This is where customer success comes in.

Customer Success 284

Customer Success Scaling Social Media Enterprise readiness 284

SaaStr

NOVEMBER 10, 2024

Top SaaStr Posts of the Week: #1. “A Lot of Great Sales Leaders — Just Aren’t Great at Selling Anymore. And Why You Really Need a VP of Sales, and Not a CRO.” ” #2. The Cloud Bubble Lasted About 18 Months. How Long Will the AI Bubble Last? #3. 83% Percent of You Haven’t Gotten AI SDRs to Work … Yet #5.

Cloud 301

Cloud AI Startup Strategy 301