SaaStr

FEBRUARY 16, 2024

Alex Kayyal and Julie Kainz, Partners at Lightspeed, shared at SaaStr Annual a framework they developed around how to think about this new era of Artificial Intelligence in SaaS, what opportunities are out there for startups, and how to think about incumbents. Together with Abhay Parasnis, founder and CEO of Typeface, they chat about what it looks like to be a builder at the forefront of Generative AI.

AI 208

AI Artificial Intelligence Healthcare New CTO 208

SaaStr

JANUARY 28, 2024

Dear SaaStr: Is There Any “Con” In Giving Our Sales Tool For Free to Early-Stage Startups? Free of course can real work, done right.: Slack Zoom Canva All built massive businesses on the back of very Free editions, even if they later turned more enterprise. Very free, in fact. All of their Free editions are amazing. Should Your Free Edition … Be Even Free-er?

Strategy 209

Strategy Onboarding Enterprise Startup 209

SaaStr

JANUARY 28, 2024

Each week, we round up our most popular content so you can catch up on anything you may have missed. Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: Venture Backed or Bootstrapped? There’s a Third Way. Just Raise One Round My Best Advice for 2024: Work Harder Beware The Overly Self-Promotional CMO (and CRO) Product-Led Growth Is Great.

Scale 194

Scale AI Cloud Enterprise 194

SaaStr

JANUARY 9, 2024

So we’ve been focusing on leveling up a lot in our content game recently: We do terrific, free, live Workshop Wednesdays with the best in SaaS now, every week at 10am PST. Bring your questions! We’ve added the wildly successful CRO Confidential series with Sam Blond, ex-CRO of Brex and now Partner at Founders Fund We’ve upgraded the SaaStr Daily and Weekly newsletters , and they now reach 200,000+ We’ve added the very popular My App Stack to help you see what top apps le

Cloud 218

Cloud SaaS 218

SaaStr

DECEMBER 9, 2023

Dear SaaStr: What’s the #1 Mistake New Sales Leaders Make? Let me just summarize my #1 observation here: the top mistake first-time sales managers make is recruiting. In that — they can’t do it. It is incredibly hard to figure out how to replicate the magic of the first 1 or 2 sales reps that work closely with the CEO. And add in a first-time sales manager who may have limited experience recruiting a team, and it gets risky.

Sales Recruiting 243

Sales Recruiting Sales Hiring Sales Management 243

SaaStr

NOVEMBER 30, 2023

So the Wall Street Journal and Bamboo HR put out a great eNPS survey of 1,600 companies, a large part of them in tech. 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 (!

Retention 231

Retention Data 231

SaaStr

NOVEMBER 30, 2023

A great product, while necessary, isn’t sufficient to build a market leader and eventually a public company. Companies that win a market are just as good at Go-to-Market as they are at building great products. General Partner Doug Pepper and General Partner and Head of Analytics at ICONIQ Growth, Christine Edmonds, share the art and science of scaling GTM at this year’s SaaStr Annual.

Scale 224

Scale Sales Hiring Scaling Outsourced Development 224

SaaStr

NOVEMBER 30, 2023

Dear SaaStr: What Do VCs Do When They Leave Their Position? It depends on if they own the place. A true “Managing General Partner” usually doesn’t so much leave as wind down, step down, slowly retire, etc. Why not? Because VC funds typically last 13–14 years each, and often 20 years to full distribution. And a Managing General Partner will often be running 2–5 of these at the same time.

Investment 220

Investment Management Software 220

SaaStr

NOVEMBER 26, 2023

Each week, we round up our most popular content so you can catch up on anything you may have missed. Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: When The Team Revolts 80% of IPOs Since 2020 Are “Broken” What Are Public SaaS Companies Taken Private At? 7.7x ARR On Average Per SaaSomomics Pilot: 57% of Venture Startups Will Need to Raise More In 2024 5 Ways To Leverage AI in Tech with Freshworks Top Podcasts This Week: 1.

Sales Hiring 187

Sales Hiring AI Startup Acquisition 187

SaaStr

NOVEMBER 19, 2023

Dear SaaStr: I sold my company five years ago and have built a net worth of ~$10 million, but compared to my friends I feel like a loser and still keep trying hard at startups that stress me out and make me miserable. What should I do? It’s crazy, but … you’re not alone. And sometimes it almost never ends. Dave Duffield made $10 billion when Oracle took over Peoplesoft … but he still had to go and co-found Workday.

PayPal 233

PayPal Startup Management Leadership 233

SaaStr

NOVEMBER 19, 2023

Each week, we round up our most popular content so you can catch up on anything you may have missed. Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: HubSpot and ZoomInfo: “Things Aren’t Getting Any Better … Yet” 5 Interesting Learnings From ZoomInfo at ~$1.3 Billion in ARR 80% of IPOs Since 2020 Are “Broken” The 5 Ways AI Will Transform Creativity with Adobe CSO Scott Belsky Before You Start as a VP — Please, Please, Pleas

AI 164

AI Acquisition Startup Strategy 164

SaaStr

NOVEMBER 9, 2023

Dear SaaStr: What are some of the “ultimate sins” in marketing and sales and success in SaaS in the early stages? My list of some bad ones: Sales: Hiring any reps you wouldn’t buy from. This never works out in the early days. Later, once you have a strong VP of Sales, it’s fine though. A bit more here. Hiring a “VP” of Sales before you have 2 scaled reps and a repeating process.

Sales Hiring 224

Sales Hiring Scale Startup Marketing 224

SaaStr

NOVEMBER 9, 2023

Dear SaaStr: What Are Your Thoughts on Co-CEOs? Like many things, I’ve mellowed a bit on this over time. I traditionally thought co-CEOs were a terrible idea. Everyone needs to know who’s the boss in the end. Who’s on the hook for raising capital, managing the board, firing and hiring the executives, etc. I thought a CEO and a President were OK, for example, but two CEOs was just a bunch of headaches in the making.

Startup 235

Startup Scaling Management Business 235

SaaStr

OCTOBER 29, 2023

Each week, we round up our most popular content so you can catch up on anything you may have missed. Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: Are We Back to a 6x World? 10+ Actionable Things You Can Do To Scale Faster In The Early Days The Chat GPT Growth Story: How AI is Changing the Way We Work The Challenge with SMB SaaS: High Growth Can Only Mask High Churn For Just So Long (Updated) Dear SaaStr: My Top Sales Rep Made $600,000 a Year —

ChatGPT 227

ChatGPT Scale SMB AI 227

SaaStr

OCTOBER 29, 2023

“My App Stack” is a new series where we dig in with top CMOs, CROs, CTOs and CEOs on just what apps they’re really using to run their business. 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 Chandar Pattabhiram, CMO at Coupa, check it out here. This week we have Nivas Ravichandran, Head of Marketing at Spendflo!

Marketing 218

Marketing Product Marketing Startup Engagement 218

SaaStr

OCTOBER 18, 2023

This year has been tougher for almost everyone — hiring freezes, budget cuts, layoffs, and macroeconomic headwinds. For those in the business of getting customers for their companies, you might be expected to cut down on spend, yet you’re still expected to grow the company and find ways to sell. Datadog CMO Alex Rosemblat took the stage at SaaStr Annual 2023 to share how marketing teams can get more deals done with less budget.

Sales Hiring 233

Sales Hiring Underperforming Technical Team Engineering Sales 233

SaaStr

OCTOBER 18, 2023

So Domo is an interesting case study on SaaS entrepreneurship. 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. Omniture is still big and it dominated web analytics especially for bigger companies in the earlier days of the internet. After a less-than-fun time being acquired, he came back and founded a next-generation enterprise analytics company, Domo.

Entrepreneurship 231

Entrepreneurship Enterprise Pricing Churn 231

SaaStr

SEPTEMBER 26, 2023

Dear SaaStr: What is The Biggest Difference Between Running a 10 Person Startup and a 100 Person Startup? The biggest structural difference is you have to hire all the VPs by employee 50–100. You won’t be able to scale this far without a full management team — VPs of Sales, Marketing, Product, Engineering, Customer Success at least. But the toughest personal challenge for many CEOs is letting go.

Sales Hiring 265

Sales Hiring Startup Scale Scaling 265

SaaStr

SEPTEMBER 26, 2023

So Klaviyo and Instacart reopened the IPO markets — from a 20 year low. We are back. At least, for the very best. Mostly. Two great leaders, worth almost $10B now and public, and both “priced” at the high end of the IPO ranges. Klaviyo is the more relevant for us in SaaS, and it’s a monster : $650,000,000 in ARR (!) Growing a stunning 56.5% at this scale (!!

Marketing 156

Marketing B2C Scaling Engineering 156

SaaStr

SEPTEMBER 26, 2023

How is AI going to impact the software and SaaS landscape of the next couple of years and also the next 5-10 years? Kristina Shen, General Partner at a16z, shares some insights into the present and future of generative AI at this week’s Workshop Wednesday, held every Wednesday at 10 a.m. PST. The Most Surprising Thing About VC This Year Shen has been in venture capital for 12 years now, and it’s been a crazy ride to watch the whole bull market back in ‘10 and ‘11 when 10x revenue was insanely ex

AI 245

AI Generative AI Venture Capital SaaS 245

SaaStr

SEPTEMBER 14, 2023

So first a caveat: I know just enough about financial accounting to be dangerous. Second caveat: I’m way, way oversimplifying things. 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 195

Acquisition Investment Headcount Banking 195

SaaStr

AUGUST 27, 2023

Dear SaaStr: How are Funds Invested by Venture Capital Firms? It varies of course, but roughly for bigger funds: Funds tend to invest in 20–40 startups over 2–4 years. Big and tiny funds may do more, but in general, this is the sweet spot. Funds use about 40% of their fund for initial, first checks They earmark another 40% for follow-on checks into later rounds in those investments over the next 2–10 years And 20% of the fund is used for fees and expenses, at least initially So a $200m VC fund m

Venture Capital 179

Venture Capital Investment Startup 179

SaaStr

AUGUST 27, 2023

Each week, we round up our most popular content so you can catch up on anything you may have missed. Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: The Irreplaceable But Toxic Employee SaaStr Annual 2023 Will Return Sept 6-8, 2023, SF Bay Area The Official Guide to SaaStr Annual 2023 Parties and Side Events!

Startup 206

Startup Scaling Metrics SaaS 206

SaaStr

AUGUST 26, 2023

Data Doesn’t Have to be Hard: Three Data Myths and How to Bust Them with Mailchimp with John Humphrey, former Head of Data Platform Product at Mailchimp John Humphrey, former head of data platform product at MailChimp and current principal at mfact, joined SaaStr live at Workshop Wednesday to discuss three data myths and how to debunk them. The first myth is that working with data is hard, but John emphasizes that anyone can start working with data by leveraging their business knowledge.

Technical Advisors 201

Technical Advisors Data Technical Review Sales Hiring 201

SaaStr

AUGUST 26, 2023

So I get a lot of podcast requests, and I think podcasts are great. They are an incredible way to communicate with your customers and prospects. Even if the absolute number of listeners and viewers is low, the quality is often high. Yet, folks tend to do the ask … wrong. Let me tell you what folks do wrong (and folks like Harry Stebbings never do): Don’t drop me on an EA to schedule.

Business 182

Business Communication Marketing 182

SaaStr

AUGUST 7, 2023

Learn about the most important SaaS metrics for founders in 2023 with the CEOs of the most metric-oriented company, monday.com, and the founder of SaaStr. Jason Lemkin, Founder of SaaStr, and co-founders and CEOs, Eran Zinman and Roy Mann of the wildly successful monday.com chat with Startup For Startup about ARR, NRR, CAC, and what it takes to beat the odds in a tougher environment.

Metrics 183

Metrics SaaS Sales Hiring Finance 183

SaaStr

AUGUST 7, 2023

Dear SaaStr: Do CEOs of big companies answer and read emails by themselves, or their assistant? Are they working on a PC at all or are they just attending meetings? This is such a great question. I remember wondering the very same thing when my last startup was acquired by Adobe. Yes, I was a VP then, but there were SVPs and EVPs and Presidents and more above me.

Startup 196

Startup 196

SaaStr

JULY 27, 2023

Dear SaaStr: What Happens To Employees When a Company Gets Acquired? The truth is, it varies, and it’s fair to have anxiety here. Generally speaking in most acquisitions: All engineering and most/all product employees will be retained. Many times, with a retention package. Sales + success individual contributors are retained, but sometimes with short-term goals.

Acquisition 158

Acquisition Finance Engineering Retention 158

SaaStr

JULY 27, 2023

Founders of 2023 ask themselves, “What does it take to raise money right now in this uncertain market environment?” Peter Specht, Partner at Creandum, shares a data-driven perspective and real-time insights into the market of very recent rounds and current VC expectations. Unfortunately, raising money isn’t the same as it used to be. Specht walks you through what has happened in the last 12 months and the best practices for today.

AI 177

AI Trends Banking Pricing 177

SaaStr

JULY 27, 2023

So this is a niche post on a niche issue, but I think an important one because I see it creating real problems all the time. The Arrogant Chief of Staff that is empowered to make big decisions, but goes rogue and makes bad ones. Or at least, lacks the life experience and maturity to make good ones. Three recent examples from just the past few weeks: Example #1: CEO of $10B+ Public SaaS Company’s Chief of Staff Never Follows Up A little while back, a CEO of a $10B+ Public SaaS Company tha

Startup 197

Startup SaaS Leadership 197

SaaStr

JULY 27, 2023

Year after year, VCs show up to SaaStr Annual locked and loaded, term sheets in hands , on the hunt for soon-to-be Unicorns to add to their portfolios. From the Founding Partners, Managing Directors and big name SaaS VCs who grace the stage. to the firms that send over a dozen of their Partners and Associates — everyone who invests in SaaS has a presence at SaaStr Annual.

Venture Capital 187

Venture Capital Banking Cloud Investment 187

SaaStr

JULY 19, 2023

Datadog is at $2 Billion in ARR and let's pause for a moment for our jaws to drop: – It's still growing 33% – It's still growing new customers 29% – It still has 130%+ NRR and 90%+ GRR – It's cash-flow positive with 19% operating margins That's why it's worth 18x ARR — Jason ✨Be Kind✨ Lemkin  (@jasonlk) July 17, 2023 So Datadog is just the SaaS and Cloud leader that just … has never stopped.

Cloud 198

Cloud Scaling Engineering Revenue 198

SaaStr

JUNE 23, 2023

Dear SaaStr: Should Your Ask a Prospect What Competitors They Are Looking At? You’ll find 90% of the time you’ll want to not just tell a client who you are competing with — but do so aggressively. And box the competition out at the start. “Great to learn about your business! Is there anyone else you are looking at to _”? Then, sales rep looks up latest tear sheer or FUD (Fear, Uncertainty & Doubt) on that Competitor.

Mobile 183

Mobile Branding Sales Business 183

SaaStr

JUNE 16, 2023

Dear SaaStr: How Many Sales Reps Do I Need? More than you probably would think. You can back into how many sales reps you’ll need in SaaS. First, figure out how much revenue you need to close in the next twelve months. Because that’s more than now. Second, calculate a reasonable attainable quota for your closers, your Account Executives. This is generally derivate of your deal size.

Scale 242

Scale Sales Hiring Sales Headcount 242

SaaStr

JUNE 16, 2023

So Carta recently put together some dat a on a topic I’ve wondered about: just how many startups allow option exercises beyond the traditional 90 day window? The answer: the general trend is just over 10% of startups have extended windows beyond the traditional 90 days for departing employees to exercise stock options. But that is extended in tougher times, like just after lockdown in 2020 … and in 2023.

Startup 222

Startup Trends Data Compensation 222

SaaStr

JUNE 16, 2023

As someone that’s been a founder, an investor, and a student of startups and SaaS for a while now, when I look back at my top mistakes, leaving any relationship broken is high on the list. Nick Mehta, CEO of Gainsight, put this high on his list of Top 10 Mistakes as well in his look back the other day : Mistake #6: Not parting ways well always In startups, relationships end.

Startup 201

Startup SaaS Business 201

SaaStr

JUNE 2, 2023

Dear SaaStr: Does Bootstrapping Through an Agency/Services Business Work? Running two businesses at once well is really, really hard. But I think if you are thoughtful about it, using an agency/services business can be a viable way to bootstrap your way into a SaaS business — as long as you transition over fairly early to doing your SaaS business 100%.

Business 216

Business Investment Software Scaling 216