SaaStr

NOVEMBER 6, 2023

Dear SaaStr: Should Co-Founders Issue Themselves 100% Vested Shares at Founding, Or Vest Over 4 Years? More here: A Simple Commitment Test For You And Your Co-Founders The post Dear SaaStr: Should Co-Founders Issue Themselves 100% Vested Shares at Founding, Or Vest Over 4 Years? Ideally, 6-7 years or even a decade. It’s demotivating.

242

242

SaaStr

NOVEMBER 19, 2023

Dave Duffield made $10 billion when Oracle took over Peoplesoft … but he still had to go and co-found Workday. So he founded Yammer and sold it for $1B+ cash. What should I do? It’s crazy, but … you’re not alone. And sometimes it almost never ends. David Sacks made tens of millions at PayPal but had to do more.

PayPal 233

PayPal Startup Management Leadership 233

SaaStr

NOVEMBER 3, 2023

Jack is an investor through his founding of Jack Altman Capital where he has invested in WorkOS, NexHealth, Owner.com, Mercury and more. Auren is an investor through his founding of Flex Capital where he has invested in Chime, Checkr, Coinbase, Flexport, Vercel and more. Jason is an investor through his founding of The SaaStr Fund.

Investment 247

Investment Communication SaaS Management 247

SaaStr

FEBRUARY 21, 2024

But whatever company you found, you are its founder forever. Leaving Some of Its Smaller Customers Behind As Blackline standardizes around $250k+ deals as growing mid-market and enterprise companies, it’s found its tough to support the smaller ones. #8. But, but — only a founder CEO can execute a vision over 20+ years.

Payment Features 198

Payment Features Scale Enterprise Software 198

SaaStr

MARCH 11, 2024

You aren’t aligned and “thinking as one” co-founding entity. Dear SaaStr: A Co-Founder is Asking for More Equity Post Fundraising. What Should I Do? It usually means something is wrong. Or at least, off: If you got the equity splits right at first, usually, big issues don’t come up later. This may be a sign you need to fix things here.

Communication 179

Communication Data Leadership 179

Tom Tunguz

JUNE 17, 2022

A round extension that sells another 15% of the company leaves a modern founding team with more ownership than its older brothers founded five or ten years ago. Across financing rounds, dilution from capital has fallen by 30-50% in that decade. Cumulative Dilution Points.

Finance 348

Finance Startup 348

SaaStr

JANUARY 10, 2024

Procore in fact was founded way back in 2002. So we haven’t checked in on Procore since after its IPO, when it was at $500m ARR. It’s a true vertical SaaS leader — “Cloud for Construction” — growing an impressive 33% at $1 Billion (!) in ARR now. And it’s a great story of going long. Not Procore.

Scale 201

Scale Payment Services Payment Features Construction 201

SaaStr

DECEMBER 21, 2023

What it looks like: Founded 2012, service management software for HVAC and more $250,000,000 in ARR in 2021, growing almost 50%, per Reuters $460,000,000 in ARR at 12/31/23, per The Information Today? Reuters are others are reporting ServiceTitan has already filed to IPO in the first half of 2024. Fingers crossed. It should be a good one.

SaaS 286

SaaS Software Marketing Management 286

SaaStr

NOVEMBER 30, 2023

They found: Comp is higher Work-life balance is better Benefits spending has gone up 20% More freedom And yet: Employees are the unhappiest they’d been at least since 2020, and probably longer 34% of employees now dread the start to the workday — up 11% from 2020 (!) This is what I’ve certainly observed. Just not as well.

Retention 231

Retention Data 231

SaaStr

JANUARY 24, 2024

Founded back in 2010, it had steady growth to $100m ARR, IPO’d quietly in 2019, then has grown 30%+ annually every year since. So sometimes steady and even is the right path. SproutSocial is one of those. That’s compounded to $360m in ARR today, and a market cap of $3.4 Billion, so about 9x ARR. Did it have a crazy Covid boost?

Social Media 210

Social Media SMB Enterprise Scaling 210

SaaStr

JANUARY 4, 2024

All of our Managing Directors on the early team have both founded companies and operate at scale. Founding a company feels the same way. When taking on something this ambitious, founder-market fit is paramount, and Poolside has it in spades. What’s the #1 bit of advice you’d give to SaaS founders today?

Management 213

Management CTO Hire New CTO AI 213

SaaStr

APRIL 10, 2024

Many in SaaS have found a way to drive their ACV and ARPU up over the past 18-24 months with price increases, more products, and more. So I’ve been doing SaaS long enough to remember when Dropbox was a super hot SaaS startup. Billion in ARR. It wants efficient growth. And as a result, DropBox’s market cap is $7.8 Billion today.

Scale 215

Scale Churn Scaling Pricing 215

SaaStr

FEBRUARY 8, 2023

So everyone knows Salesforce, founded in 1999, originally to manage your salesforce. But there’s another SaaS leader that almost everyone in B2B software also uses also founded in 1999 — to manage their events. It’s still around, too. A lot of it is a bit old, and hard to use, and expensive. Billion market cap.

Marketplace as a Service 272

Marketplace as a Service Software Review Cloud B2B 272

SaaStr

NOVEMBER 15, 2023

Only Founded in 2011. The company is still growing a jaw-dropping 37% at almost $3B ARR — and it’s generating incredible free cash flow. Security remains hot. And in fact, the stock is up 94.7% this year! It’s market cap is almost $50 Billion. nottooshabbby pic.twitter.com/VOlpHaWcVd — Jason ✨Be Kind✨ Lemkin  ??

Cybersecurity 249

Cybersecurity AWS Benchmarks Cloud 249

SaaStr

MAY 4, 2021

It’s old, founded in 2001. But Five9 found a way to reignite new logo growth. Five9 is a $12B SaaS company many of you haven’t heard of, but it’s an interesting beneficiary of Covid in many ways. While we all saw Zoom and Shopify explode during Covid, Cloud call centers boomed just as much. 12 Billion! at $550m ARR.

Systems Review 341

Systems Review Technical Review Software Review Cloud 341

SaaStr

DECEMBER 20, 2023

or at least cash flow positive) all just in Year 10 since founding. But we at least know enough to put together 5 Interesting Learnings! They were $1.7B+ ARR in October , so let’s call it close to $2B at the end of the year, growing 40%+ at that scale –and profitable! (or That’s … pretty epic. Wow, what a story!

AWS 245

AWS B2C AI Scaling 245

Tom Tunguz

MARCH 24, 2024

A 2020 MIT study found 1 robot in a manufacturing facility replaced 3.3 In 2016, the question was easy to answer : sell Ironman not Robocop. Technology hadn’t reached the level of sophistication we have attained today where AI is 90% as capable as a high-school student, the MMLU benchmark for AI is precisely this. more productive.

AI 158

AI Software Engineering Benchmarks Startup 158

SaaStr

AUGUST 5, 2023

Usually, the founding partners or the more senior partners control both (1) most of the profits, the “carry” and (2) own the management company, and keep more of the “fees”. Many folks are “general partners” but the founding investors still run the place. Dear SaaStr: Why Do VCs Leave Their Firms to Start Their Own Funds?

Leadership 181

Leadership Management 181

SaaStr

SEPTEMBER 20, 2021

Still, I was wondering — how old are founders of top SaaS companies at IPO (when the real job starts in some ways), and at founding? The answer: of the current batch of newer public SaaS companies, the average CEO is 43 at IPO and 32 at founding. Does “age” even matter any more for SaaS founders, if it ever did?

SaaS 311

SaaS Cloud Startup Scaling 311

SaaStr

FEBRUARY 14, 2024

This is the fourth annual Customer Success Leadership Study brought together by ChurnZero, ESG, SaaStr, and Hubspot. The report provides a definitive overview of the customer success landscape and features insight from more than 1,200 CS leaders worldwide — making it the largest study in the industry for customer success. What’s in the pipeline?”

Customer Success 224

Customer Success Sales Hiring Scale AI 224

SaaStr

OCTOBER 5, 2023

In my second start-up, I found this help more in my management team. Dear SaaStr: As a Founder, How Do You Deal With Stress In a Startup? Dealing with stress is important, especially for founders, who do have to hide … some of it. More than in 21+ years. For me at least, 4 things made a material impact: #1. Get to cash-flow positive.

Startup 245

Startup Management Business Leadership 245

SaaStr

MARCH 12, 2021

A few: eLance was founded in 1998 as an early freelancing website. More here : GoDaddy was founded in 1997 remains a leader in domain names but expanded into web sites, ecommerce and more — and is worth $13B today ! More here : On24 was founded in 1998 is a niche Zoom competitor you might have heard of if you do webinars.

SaaS 273

SaaS B2B Enterprise Revenue 273

SaaStr

NOVEMBER 13, 2023

It worked out but maybe I should have found at least one person who would hire me before I did that. Dear SaaStr: What Has Been Your Biggest Career Mistake? Maybe not slowing down just a little bit. I had no idea what I would do next and had zero savings. Maybe could have gone a little more slowly. for the team, and just started doing it.

Venture Capital 236

Venture Capital Startup Investment Leadership 236

SaaStr

SEPTEMBER 28, 2023

But I found it interesting how Salesforce has come up with 2 clear policies on engineering vs. sales & marketing. So most everyone is still working on figuring out just how distributed, hybrid, etc. we all want to be — and can be. ” These are tough issues and I don’t think there are perfect answers.

Scale 169

Scale Engineering Marketing Sales 169

SaaStr

OCTOBER 24, 2023

Founded back on April 1, 1972? The ones folks want, but could cut because they already have some of that functionality in their core suite. Who’s winning these days: often the core suite itself. Salesforce is back to aggressive hiring. And ooooold SAP? Their Cloud business is on fire. From a vendor they truly trust. And rebuild.

Cloud 222

Cloud Scale Sales Hiring Business 222

SaaStr

DECEMBER 29, 2023

He found it didn’t really matter how long the trial was, 14 vs 21 vs 30-day free trials didn’t matter. Dear SaaStr: How Long Should a Free Trial Be for SaaS Products? It doesn’t really matter. What I mean is, this is one of those things in SaaS that is over-analyzed, as if it will make a magical difference. Say, 30 days.

SaaS 189

SaaS User Experience Startup Investment 189

SaaStr

JUNE 19, 2022

I found and hired my VP of Marketing). I went to meet with one of my angels and mentors when things were probably toughest at my last start-up. My co-founder had walked out the door. We had about 4 months left of cash. I was out of ideas. Yes, we had customers — hundreds — but not nearly enough. Enough, he said. Go get on some jets, he said.

Pricing 310

Pricing Marketing 310

SaaStr

JUNE 21, 2023

It seems simple enough, but it’s not always easy, as founding CEO and co-founder of LaunchDarkly, Edith Harbaugh, learned firsthand as she took the company from zero to over $100M. $100M ARR doesn’t happen overnight. After LaunchDarkly got their series A, things took a turn. But as you can guess, it didn’t work out. And it was true.

Sales Recruiting 238

Sales Recruiting Sales Hiring Underperforming Technical Team Pricing 238

SaaStr

DECEMBER 11, 2021

But those early customers that somehow found you, with no brand, no PR team, no Platinum Booth at Dreamforce. They had an extreme need, so they found you, and … you won’t lose them. We’ve talked about how all the Second Timers are hiring in customer success way early , ahead of sales, ahead of revenue.

Sales Hiring 271

Sales Hiring Customer Success Headcount Churn 271

SaaStr

DECEMBER 17, 2023

Additionally, Kyle is a founding member of the Toronto chapter of Pavilion, a global community of revenue leaders and operators. Last week we had a great one with Udi Ledergor, Chief Evangelist at Gong, check it out here. This week we have Kyle Norton, CRO at Owner! #1. What’s your core stack of apps today? Game changing addition for us. #3.

Scale 236

Scale AI Leadership Innovation 236

SaaStr

JULY 7, 2023

But I wish I’d found a way to take another 60 or 90 days to solidify the team before we truly hit the ground running. Dear SaaStr: What Were the Biggest Mistakes You Made as a Founder-CEO? I’ve made so many, it’s hard to boil it down to two. But let’s focus on the earliest days, in Year 1. Not really. The demands are high.

SaaS 224

SaaS Management Marketing Leadership 224

SaaStr

FEBRUARY 7, 2024

But, what Morgane found was that their newly minted large team of SDRs didn’t actually know how to go outbound to the developer audience. But, what Morgane found was that their newly minted large team of SDRs didn’t actually know how to go outbound to the developer audience. No humans involved.

Scale 216

Scale Sales Hiring Strategy Marketing 216

SaaStr

JULY 9, 2021

We took a look at this a while back on SaaStr, and found that roughly 20% had a “core founder” or solo founder. E.g., companies like Elastic, Fastly and Twilio weren’t literally solo founded, but in the end basically ended up that way. More on that here: At the Top SaaS Companies, Founder-CEOs Own ~15% at IPO.

Startup 237

Startup Cloud SaaS 237

SaaStr

NOVEMBER 22, 2023

Steady, Strong Growth — Since 2006 Appfolio was founded way back in 2006, and they never quit. There are several big leaders in property management software, and AppFolio is one of them. It’s doing well, especially in today’s markets. Billion market cap, even with lower than standard gross margins. Let’s dig in.

Payment Services 227

Payment Services Payment Solutions SaaS Payments Payments 227

SaaStr

MARCH 14, 2024

Prior to Inspired Capital, Lucy was on the founding team at Paperless Post, where she spent a decade as COO building the company to serve over 100M hosts and guests. What’s your pulse check on the venture markets right now, today? Lucy is a General Partner at Inspired Capital.

Scale 187

Scale B2B Investment Acquisition 187

SaaStr

OCTOBER 18, 2023

After a less-than-fun time being acquired, he came back and founded a next-generation enterprise analytics company, Domo. Founder Josh James had one of the earliest $1B+ exits in SaaS when Adobe bought his first start-up, Omniture, for $1.8 Billion way back in 2008. But then … things slowed down, to 5% a year at $360 million in ARR.

Entrepreneurship 231

Entrepreneurship Enterprise Pricing Churn 231

SaaStr

SEPTEMBER 24, 2023

Previously, she co-founded Fraiche Yogurt, a successful chain of yogurt stores in the Bay Area. I always learn a lot from these — they are in essence a best practices list from each leader. Last week we had a great one with Sarah Scharf, VP of Marketing of Vanta, check it out here. What’s your core stack of apps today?

Marketing 242

Marketing Leadership Engineering Enterprise 242