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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. Reflecting on Company Outcomes as a Founding CEO We started with Brian flipping the tables a bit and asking Jason a question to kick off the interview: “I know this is a podcast supposed to be interv
Veeva is the dominant cloud software provider for life sciences – serving pharmaceutical, biotech, and medical device companies with mission-critical applications for drug development, clinical trials, regulatory compliance, and commercial operations. Started as “Salesforce for Pharma” in 2007, now the essential technology backbone for companies bringing medicine to market.
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. A failed VP of Sales hire doesn’t just cost you immediate revenue—it creates a devastating ripple effect: You lose the second-order revenue (up to 6x the initial l
The SaaS PE market is heating up again, and Thoma Bravo just made a big statement buying SaaS restaurant pioneer Olo for $2 Billion. Yesterday, Thoma Bravo announced they’re acquiring restaurant tech platform Olo (NYSE: OLO) for $2 billion in an all-cash deal. That’s $10.25 per share — a whopping 65% premium over Olo’s closing price on April 30th (the last trading day before acquisition rumors started swirling).
Dear SaaStr: How Should Founders Build Their First Customer Success Team? Building a Customer Success (CS) team early is critical for SaaS startups. Here’s how early-stage founders should approach it: Hire Early, Even Before It Feels Necessary Don’t wait until churn becomes a problem. Customer Success should be a single-digit hire—ideally, your first 5-10 employees should include at least one CS hire.
Meet Wyatt Jenkins: From Construction Sites to Chief Product Officer If you want to understand how vertical SaaS companies scale to $1B+ in revenue while staying true to their customers, there’s no better person to learn from than Wyatt Jenkins, Chief Product Officer at Procore Technologies. Wyatt’s journey is uniquely suited to leading product at a construction technology company.
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% (!). In the words of founder CEO Andrew Bialecki: “There’s no downturn at Klaviyo.” 5 Interesting Learnings: #1. 110% NRR from 157,000 SMBs Yes, it can be done, 110% NRR from SMBs.
So we’ve covered HubSpot more than any other SaaS leader on this 5 Interesting Learnings series, in part because so many of us use HubSpot ourselves, and in part because its metrics and use cases are so like many of the apps we build and sell ourselves. They recently did an Analyst day though that had some more great data that I thought was super interesting, and worth a deep dive. 5 More Interesting Learnings then: #1. 75% of Customers Are Onboarded By Partners Partners don’t just
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. 2 Cold Emails I Funded For Millions #2.
Dear SaaStr: My Customer Hasn’t Paid. When is it Worth it to Hire a Collections Agency to Get The Money? Never. I know it’s frustrating, but if you’ve turned off the app and they still won’t pay, it’s just time to move on. It’s almost never worth it to hire a collections agency in SaaS. Here’s why: It destroys the relationship.
So Okta rose to rapid growth and IPO as the stand-alone leader in enterprise identity for apps, acquired Auth0 to own it for developers, and now coming up on $3 Billion in ARR, it has settled into a more mature state: $2.75B in ARR Growing 12%, projected to slow to 10% Non-GAAP operating margins of 27% Free Cash Flow margins of 35% (!) $18B market cap, so ~6x ARR Net net it’s a story of new customer growth of 7% combined with slowing NRR of 106%.
Dear SaaStr: What are the most common mistakes first-time founders make when building enterprise sales teams? The most common mistakes first-time founders make when building enterprise sales teams are surprisingly consistent. Ive seen them over and over, and Ive made a few of them myself. Heres the breakdown: Hiring a VP of Sales Too Early : This is a classic.
Dear SaaStr: What Are Some Red Flags an Investor Might Not Be Serious? First, if youre not sure they want to invest they probably dont want to. And its 100% OK to ask. Just ask. The One Question To Ask At The End of Every VC Pitch: What Are The Odds You Would Invest? Just ask what are the odds theyd want to invest, based on what they know now. Beyond that here are clear red flags that an investor might not be serious about investing in your startup include: Overly Complex Terms : If the invest
Dear SaaStr: Our Biggest Potential Customers Are All Asking for Custom Features. When Do We Say Yes? This is a classic enterprise SaaS challengebalancing the need to close big deals with the risk of overextending your team on custom work. Selling 90% out-of-the-box is great, but that 10% custom work can quickly spiral out of control if youre not careful.
What does it take to build and scale a vertical SaaS giant over two decades? According to Tooey Courtemanche, CEO and Founder of Procore, its about focus, perseverance, and a relentless commitment to customer success. In a recent conversation with SaaStr CEO and Founder Jason Lemkin, Tooey shared insights into his 23-year journey as CEO of Procore , the leading SaaS platform for construction management.
The New Era of Customer Success: Deep Insights from Slack, Mulesoft and OpenAI Leaders What happens when you get customer success leaders from three of tech’s most iconic companies in one room? You get a masterclass in how modern SaaS businesses are transforming CS from a cost center into their secret weapon for hypergrowth. Why Traditional Customer Success Is Dead The old playbook of treating CS as your renewals team is officially obsolete.
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. In a recent conversation between HubSpot Chairman and co-founder Brian Halligan and SaaStr Founder and CEO Jason Lemkin, they shared their advice on what actually works when hiring VPs and building your SaaS executive team.
Dear SaaStr: How Much Does a Typical B2B SaaS Company Spend on Digital Marketing per Year? It’s tough to spend even $1m a year effectively on most digital spend for most categories of B2B software: Putting aside Unicorns and folks that have raised monster rounds, in my experience, most enterprise SaaS companies struggle to deploy more than $40k-$50k a month on Adwords effectively.
Former Head of Revenue at BILL and HubSpot Americas leader Michelle Benfer recently joined us on a SaaStr Workshop Wednesday share her insights on one of the most critical roles in any SaaS organization: the frontline sales manager. Having led sales teams of 500+ at BILL and 800+ at HubSpot, Michelle has unique insights into what makes great frontline managers and why investing in them is crucial for sustainable growth.
So clearly AI is rapidly changing the way we do sales, but how will it all shake out? Over in the contact center and post-sales space, we can already see 20%+ of customer support execs been routinely replaced by AI. But what about the more personal sales side? AI SDRs have taken off more quickly than AI AEs (although personally, I suspect more value will be in AI SEs and AEs that can answer my deep product and pricing questions instantly, without games).
So some Cloud and SaaS stocks are on fire, even now. And then … there is Palantir. The fire of the fire. It’s up +162% in the past year, and is now worth $95 Billion (!) at $2.7 Billion ARR. That’s a jaw-dropping 35x ARR. Goodness. Why is Palantir the highest valued public SaaS and Cloud stock? $2.7 Billion in ARR Growing 27%, and importantly — re-accelerating. 22% free-cash margins, and now GAAP profitable Customer count up 41% year-over-year It’s the bright, AI
Don’t look now but guess who’s crushing it in the frenetic age of AI? Oracle. SAP. And enterprise leader ServiceNow. Crushing it. 22% growth at $12.5 Billion in ARR — and accelerating. And AI is the accelerant. Even for some of the established leaders in SaaS and enterprise software. ServiceNow: the renewal rate every B2B company dreams of Even at $12.5B ARR, they just … never leave pic.twitter.com/6oGigsHnON — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) July 23,
Dear SaaStr: How Do You Best Pick and Choose Board Members and Senior Advisors? Choosing board members and advisors is one of the most critical decisions you’ll make as a founder. These are the people who will guide you through the toughest challenges, help you scale, and, frankly, have a huge impact on your happiness as a founder. A few thoughts: Prioritize Trust Above All Else : You’re going to be working with these people for years, through good times and bad.
Dear SaaStr: How Should I Calculate Gross Dollar Retention For Our Investors? Gross Dollar Retention (GRR) is a critical metric for SaaS businesses, especially when presenting to investors. It tells them how much of your revenue base you’re retaining, excluding any upsells or expansions. Here’s the best-practice way to calculate it: Start with your Beginning ARR (Annual Recurring Revenue) : This is the ARR from your existing customers at the start of the period you’re measuring.
The major SaaS providers have announced another round of significant price increases for 2025, continuing a trend that’s putting pressure on enterprise software budgets across the board. After years of relatively stable pricing, these companies are leveraging their market positions to drive revenue growth through higher per-seat costs. Salesforce: The 6% AI-Driven Increase Salesforce implemented a 6% price increase for its Enterprise and Unlimited Editions, effective August 1, 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. This isn’t just about getting deals done—it’s about deeply understanding your sales process, your customers, and what works (and doesn’t) in your pitch.
So Jamin Ball of Altimeter has a great summary of the cumulative revenue growth of all public SaaS companies … and it’s not a great story: Aggregate net new ARR added in Q1 from the software universe isn't looking good! Down nearly 30% YoY from Q1 last year pic.twitter.com/9MLyLe3XXf — Jamin Ball (@jaminball) June 5, 2025 Bottom Line Up Front : The aggregate cloud software market just delivered its worst quarterly performance in years, with net new ARR additions plummeting
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. And more importantly, revenue and user growth that is accelerating at scale.
Dear SaaStr: What Should I Do in a Sales Audit? A sales audit should be comprehensive and focus on identifying strengths, weaknesses, and opportunities across your sales process. Heres what to include: Pipeline Health : Review the pipeline metricsdeal velocity, win rates, average deal size, and pipeline coverage. Are there enough opportunities at each stage to hit your targets?
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%. It’s been a tale of two worlds.
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. 53% EBITDA.
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. The second time, my first co-founder and I started working together before the idea came together.
Dear SaaStr: What is RevOps Responsible For in a B2B Company? Managing revenue operations (RevOps) in a SaaS company is all about aligning sales, marketing, and customer success to drive growth efficiently. Here are some best practices that I’d recommend: Centralize Data and Metrics RevOps thrives on data. Build a single source of truth for all revenue-related metrics—pipeline, churn, CAC, LTV, NRR, etc.
We took a look at the SaaS leaders that are doing well today, in today’s world and that have IPO’d in the past few years. Samsara, Toast, Klaviyo, ServiceTitan and Procore. Their Average Growth Rate in Year Before IPO: 63% (excluding prior generation) The Numbers *Top performer from prior generation of SaaS IPOs (2010-2015 era) The SaaS Leaders: 1.
Dear SaaStr: How Do I Know If My New VP of Sales is Working Out? This is one of the most discussed topics on SaaStr, and a deep dive here: The 30-Day Test: How to Know if Your VP of Sales Will Succeed In a nutshell, you’ll know if your VP of Sales is working out by looking at two things: results and team-building ability. A great VP of Sales should start showing meaningful progress within one sales cycle—no excuses.
How Canva’s CCO Built a $7B Enterprise Motion While Preserving PLG Culture Rob Giglio, Canva’s Chief Customer Officer, shares the playbook for scaling from 170M to 230M monthly active users while building enterprise sales without compromising company culture. Top 5 Takeaways 1. PLG-to-SLG is Far Easier Than SLG-to-PLG Going from product-led growth to sales-led growth is significantly easier than the reverse.
Dear SaaStr: What Are The Top Worries Founders Have As They Start to Scale? B2B SaaS founders tend to share a lot of common concerns, especially as they navigate the different stages of growth. Here are some of the big ones I’ve seen repeatedly: 1. Customer Concentration Risk: Founders often worry about having too much revenue tied to a single customer.
Dear SaaStr: How Do I Hire a Great VP of Sales? It’s a classic SaaStr topic and a great deep dive is here: Hiring a Great VP of Sales: The New, Latest Edition with Jason Lemkin (Video + Pod) Hiring a great VP of Sales is one of the most critical decisions you’ll make as a founder. Get it right, and they’ll scale your revenue and team. Get it wrong, and you’ll lose a year—or more.
Dear SaaStr: How Long of a Ramp Period Should I Give a New VP of Sales? Look, to be clear, the best ones just hit the ground running. Their first week and really even their first day. Everyone else … looks a little lost when they start 😉 For a Head of Sales at a seed or Series A startup, you should give them one full sales cycle —usually 90 days—to show meaningful progress.
Dear SaaStr: How Do I Ramp a New Sales Rep at a Seed Stage Start-Up? Ramping a sales rep quickly at a seed-stage company is critical because you don’t have the luxury of time or resources to wait for them to figure things out. Or usually, a VP of Sales to handhold them for a while when they start. Here’s how you can accelerate their ramp effectively: Start with Hands-On Training Don’t throw them straight into selling.
Figma has just unleashed its non-confidential IPO filing, and it’s … epic. Here’s what Figma looks like today: 📊 Core Metrics $821M LTM revenue (46% YoY growth) $913M ARR at Q1’2025 91% gross margins (best-in-class) 18% non-GAAP operating margin (profitable!) 132% net dollar retention $1.5B+ cash, zero debt 🏢 Market Position 78% of Fortune 2000 use Figma 76% of customers use 2+ products Millions of weekly active users 13 years from founding to IPO filing 🚨 FIGMA S-1 DR
Dear SaaStr: I’m Joining a Start-Up as Head of Sales At Just $1m ARR. What Should I Do First? First off, congrats on the role—it’s a big deal. But seed stage is tough. You’re building from scratch, and there’s no playbook handed to you. And you really are going to have to be both an AE yourself as well as the “boss” for a while. So let’s get you on track to crush it: Master the Product and ICP (Ideal Customer Profile) on Day 0.
So ICONIQ Growth is back with their 2025 State of AI Report: Survey Overview It has some great data from 300 high growth software companies building AI products. Survey Methodology & Sample Size 300 executives surveyed at software companies building AI products (April 2025) Respondent roles: CEOs, Heads of Engineering, Heads of AI, Heads of Product Geographic split: 88% North America, 12% Europe Data collection: Anonymous external survey including some (but not all) ICONIQ portfolio companie
Dear SaaStr: How Should Startup Founders Approach Early-Stage Hiring? Early-stage hiring is one of the most critical things a founder will do—it sets the foundation for everything else. Here’s how you should approach it: Be relentless about recruiting. Relentless. To be a great CEO, you have to force yourself to be a great recruiter. This means dedicating serious time—15 hours a week minimum—to sourcing, interviewing, and closing candidates.
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