SaaStr

DECEMBER 30, 2024

Dear SaaStr: What is it like to be pitched by startups as an investor? There are really three modes from a VC perspective during a fundraising pitch: You Almost immediately want to do the investment. This is 80%+ of the investments Ive done. The post Dear SaaStr: What Is It Like to be Pitched by Startups as an Investor?

Startup 261

Startup CTO Investment Marketing 261

SaaStr

OCTOBER 13, 2024

Lemkin Change his Point of View on The Value of a COO for Earlier Stage Startups? I try to work with (and invest in) CEOs that are better than me. Lemkin Change his Point of View on The Value of a COO for Earlier Stage Startups? Dear SaaStr: Why did Jason M. they all failed or came up way short. appeared first on SaaStr.

Sales Hiring 260

Sales Hiring CTO Hire Scale Startup 260

SaaStr

JUNE 22, 2025

Growth rates are normalizing, companies are focusing more on profitability, and the market is rewarding sustainable business models over growth-at-all-costs.

B2B 219

B2B Data Scale Startup 219

Tom Tunguz

MARCH 4, 2025

As startups scale, effective management becomes the difference between chaotic growth and sustainable success. After analyzing hundreds of posts on startup management, I’ve distilled the key pieces of advice that founders and leaders should keep in mind.

Startup 270

Startup Management Scale Construction 270

SaaStr

JUNE 20, 2025

And the evidence is mounting that AI startups aren’t just complementing SaaS — they’re actively hunting traditional SaaS incumbents for lunch. The Billion-Dollar AI Unicorn Factory The scale of AI startup funding isn’t just impressive — it’s existential for SaaS: The AI Billion-Dollar Club: OpenAI : $8.4

AI Search 289

AI Search Artificial Intelligence AI CTO Hire 289

SaaStr

JUNE 13, 2025

Andreesen Horowitz recently pulled some great data from the deals its invested in and looked at. What “Working” Means in the Era of AI Apps: The New Enterprise Benchmarks That Matter One of the most common refrains in the generative AI era is that “startups are growing faster than ever” — often with fewer resources.

Enterprise 175

Enterprise AI Startup Benchmarks 175

SaaStr

JUNE 5, 2025

The New Rules of AI Investing: Why Speed Beats Strategy and Labor Budget Is the New Software Budget The pace of AI advancement has fundamentally broken our traditional frameworks for thinking about technology adoption, market timing, and competitive moats. ” This represents a fundamental shift in venture investing criteria.

Software Review 249

Software Review Technical Review AI Development Team Review 249

SaaStr

MARCH 14, 2023

Q: What are some common mistakes that investors make when evaluating potential startup investments (such as Seed or Series A)? A few I’ve made and watched others around me make: Invest in good traction with a pretty good but not great CEO. Investing when you aren’t sure but someone else really successful is investing.

Investment 346

Investment Startup Scaling SaaS 346

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 312

Venture Capital Software Review Investment Startup 312

SaaStr

OCTOBER 25, 2024

Tomasz Tunguz , General Partner at Theory Ventures, shares nine observations from a Go-To-Market survey Theory Ventures did with hundreds of startups, 68% of them early-stage, well-funded, mostly mid-market ACV, and 25% remote. Six months ago, security was the number one prohibition preventing businesses and software companies from buying AI.

Venture Capital 331

Venture Capital Marketing AI SaaS 331

SaaStr

DECEMBER 27, 2024

AI in B2B SaaS: The Incumbent Advantage On the AI revolution in B2B software, it’s the age-old ‘startups are innovating and racing to get distribution, and the bigger companies have distribution and are racing to innovate.’ ’ The twist this time is the data is very hard for startups to acquire or accumulate.

AI 284

AI Marketing SaaS Interviewing 284

SaaStr

APRIL 1, 2023

The same things happened in VC and investing. I did some of this myself, both on people and investments. Better to do with fewer people, fewer investments, fewer initiatives. The post Lowering the Hiring (And Investing) Bar Didn’t Work appeared first on SaaStr. They just assumed it would come.

Sales Hiring 312

Sales Hiring Investment Leadership Startup 312

SaaStr

NOVEMBER 13, 2024

But it’s clear that it’s still in the investing phase, and increasing spend in sales & marketing. New Startups and Companies and Enterprise Strong. Outside of a pre-IPO phase, Klaviyo has been cash-flow positive or close for most of its history. Just not as quickly as overall revenue growth. #4. SMB Weaker.

Scale 301

Scale SMB Scaling Enterprise 301

SaaStr

FEBRUARY 11, 2025

This is epic opportunity to showcase your AI Startup. The winner(s) will receive funding from the Mayfield AI Garage, who are at the forefront of investing in cutting-edge tools at the intersection of SaaS and AI. If you’re building the next AI breakthrough in SaaS, pitch your startup at the MayfieldAI AI Demo Stage at SaaStr.

AI 300

AI Startup Innovation Investment 300

SaaStr

JULY 6, 2025

Gross contributed his expertise in early-stage investing and startup acceleration from his tenure at Y Combinator, where he helped identify and nurture some of the accelerator’s most successful companies. It’s just too much litigation risk People say dumb things they shouldn’t every single day — Jason ✨👾SaaStr.Ai✨

Venture Capital 312

Venture Capital Artificial Intelligence Technical Advisors Scale 312

SaaStr

JULY 11, 2025

The Investment Story Syllable has raised $103M total funding, including a $40M Series C led by TCV, with backing from Oak HC/FT, Section32, and Verily. Recognized as CB Insights’ most promising startup in healthcare for 2022, picked as a leader from a pool of 7,000 companies. Who Should Evaluate Syllable.ai

Payment Solutions 267

Payment Solutions Scale AI Payment Services 267

SaaStr

JANUARY 5, 2023

Salesforce is ceding the startup CRM market to HubSpot. But I would tell every startup I invested in or worked with to move onto Salesforce — at least once they hire a real VP of Sales. Now I just see so many fast-growing startups now just starting on HubSpot, but staying on HubSpot. Does it matter?

Startup 71

Startup Sales Hiring Scale Investment 71

SaaStr

SEPTEMBER 2, 2024

Dear SaaStr: Should You Always Ask a Co-founder to Invest Their Own Money? Yes, you need money one way or another to startup. And many times even a small investment will be very stressful for some co-founders. I made 12x on that investment. Especially if they haven’t really made any money yet, and you have more.

Investment 307

Investment Startup Leadership 307

SaaStr

JULY 3, 2025

✨ Lemkin (@jasonlk) July 1, 2025 While everyone’s watching the flashy AI startups and hyperscalers duke it out, two enterprise software giants are quietly crushing it in the Age of AI. These companies have legacy codebases, technical debt, and organizational complexity that would make most startup founders break out in cold sweats.

AI 236

AI Enterprise Cloud Scale 236

SaaStr

DECEMBER 23, 2024

Share everything anyone would want to know to invest in you. But unless you are raising from folks that truly invest pre-revenue, investors are going to want to see 3 strong months of growth in a row. If nothing else, point out an existing investment or two theyve made that is somewhat similar to yours. # Share it all.

Venture Capital 274

Venture Capital Investment AI Metrics 274

SaaStr

JULY 24, 2024

In a recent Workshop Wednesday, SaaStr Founder and CEO, Jason Lemkin sat down to discuss 9 signs a startup isn’t going to make it. So, let’s look at the nine signs a startup will likely not be a real success. Sign #2: You’re Too Slow to Hire VPs If you want to gauge momentum in a startup, see how quickly they hire VPs.

Sales Hiring 301

Sales Hiring Startup Scale SMB 301

Tom Tunguz

SEPTEMBER 15, 2022

Not too long before the public market correction, high-growth startups routinely commanded 100x ARR multiples. When modeling investment cases, VCs often use a basket of comparables - not a single transaction - to justify prices, even if that single transaction is a firecracker that lights up the entire night sky.

Startup 355

Startup Acquisition Pricing Revenue 355

SaaStr

MAY 12, 2023

This is consistent with my experience and across 30+ investments. More at the full report here : The post SaaS Capital: Across 1,500 SaaS Startups, Yearly Contracts Don’t Actually Increase NRR appeared first on SaaStr. So keep increasing that NRR target as you march to $20m ARR!

Startup 362

Startup SaaS Retention Churn 362

Sales Hacker

NOVEMBER 29, 2024

GTMfund’s 3 Areas of Focus for Investing Thanksgiving weekend is always a period of reflection and gratitude. Reflection across go-to-market trends, but also on the investment front (not to mention community !). A common misconception is that the name is representative of the type of software we invest in.

Investment 110

Investment Technical Review Development Team Review Scale 110

SaaStr

SEPTEMBER 14, 2023

But with that out of the way, let’s talk just enough about financial accounting to explain why Big Tech Companies both acquire smaller ones — and do corporate VC investment. Because in the short-term, it often costs basically close to nothing to acquire a smaller startup with cash on hand, or do a corporate VC investment.

Acquisition 299

Acquisition Investment Headcount Banking 299

SaaStr

SEPTEMBER 9, 2024

When I look across my investment portfolio for past 11 years , the #1 issue I think isn’t pricing, or TAM, or making a terrible mishire, or competition. I’m seeing all across my investments that are 5, 8, 10, 12+ years out. I’m seeing all across my investments that are 5, 8, 10, 12+ years out. They’re not truly multi-product.

Startup 300

Startup SaaS Investment Enterprise 300

SaaStr

JUNE 14, 2025

Successful startups balance optimism with realism by presenting a compelling vision while grounding their projections in credible, data-backed assumptions. Use a Bottom-Up Approach for Projections Startups often get into trouble by pitching top-down projections, like “If we capture 1% of a $10B market, we’ll hit $100M ARR.”

Scale 235

Scale Sales Hiring Benchmarks Churn 235

SaaStr

JANUARY 27, 2024

Dear SaaStr: What are some common reasons for the failure of startups? My experience across leading 30+ seed investments, including 4 billion+ exits so far, on why startups fail: Not 200% committed to winning no matter what. How can these mistakes be avoided to increase their chances of success? Just not a huge one.

Startup 282

Startup Scale CTO Pricing 282

SaaStr

DECEMBER 25, 2023

G2 had us back for another great deep dive on just where SaaS investing is there days, and it was a great panel: Accel Partner Arun Mathew Inspired Capital Founder & Managing Partner Alexa von Tobel Salesforce Ventures Managing Partner Paul Drews and Jason Lemkin! Low investment multiples pose a key challenge.

B2B 282

B2B Investment Venture Capital SaaS 282

SaaStr

JANUARY 2, 2024

ARR, Zendesk today gets 14% of new business from startups. On top of that, if you look at their top accounts globally, 33 of the top 50 customers by ARR are startups. This is where they started, but startups weren’t adopting the product as much with a discount, and there was a lot of conflict with the sales team. A free term.

Startup 262

Startup Scale Underperforming Technical Team AWS 262

SaaStr

JULY 9, 2024

Imagine a $150m seed VC fund that buys 15% stakes in each startup. Yes, you get more time to see how the startups are doing, so that’s easier. Those rare investments that return enough money to the VC fund to pay off at least 1x the total fund size. Investing in the #3 or #4 in a space? An epic amount! A 1% stake?

Investment 302

Investment Venture Capital Social Media Startup 302

SaaStr

APRIL 6, 2024

Dear SaaStr: What Will Venture Capitalists Do if Our Startup is a Loss? Bill said] ‘most startups do fail, so the odds were that Fanbase would fail , not succeed. A VC fund will typically do 30-ish investments per fund. of the fund, on average, per investment. Typically, though, that’s over 3–4 rounds of investment.

Startup 292

Startup Investment Leadership 292

SaaStr

OCTOBER 31, 2023

Dear SaaStr: What Did You Learn From Your Worst Venture Capital Investment? You can’t keep investing in the same companies, at the exact same stage, same valuations, etc. When I’ve cut a corner here and invested in startups with customers that aren’t super-happy, it hasn’t worked out as well. You want to move quickly.

Venture Capital 273

Venture Capital Investment CTO Churn 273

SaaStr

JUNE 25, 2025

This wasn’t just a startup necessity—it was a cultural decision that permeated the entire organization. But we will invest in this, and in six months we’ll be able to deliver it to you. “There was an early-stage customer—a law firm at 4 PM—that had an email system issue.

Cybersecurity 256

Cybersecurity AI Scale CTO Hire 256

SaaStr

JANUARY 8, 2024

But it isn’t, so I’m going to try to help by being brutally direct: No VC on Planet Earth Wants to Invest in a Startup with Mediocre Growth None. Ask them if they’d invest again. Snail image from here ) The post Look, No VC Wants to Fund a Startup With So-So Growth. They’re in for a dollar.

Startup 339

Startup Investment Business 339

SaaStr

MAY 30, 2024

So I firmly you believe you can build an incredible SaaS startup from anywhere now, or at least, any major-ish tech center. VCs really don’t want to invest 100% on Zoom anymore. Of Pre-Seed Rounds Are to California Startups per Carta appeared first on SaaStr. Heck, Oracle apparently is moving to Nashville! What do I mean?

Startup 307

Startup Investment SaaS Data 307

SaaStr

NOVEMBER 28, 2024

I try to look at two things in Vertical SaaS startups, at least when investing : Will everyone in the vertical / industry use it? Dear SaaStr: How Big Should The Addressable Market Be to Go into Vertical SaaS? and Is the app so core, or at least is on a path to become so core, that they can charge $20,000+ a year for it?

Payment Solutions 261

Payment Solutions Inbound Sales Team Marketing Scale 261