SaaStr

MAY 27, 2025

So we’ve been proponents of customer success at SaaStr since the earliest days, since our first SaaStr posts in 2012. The magic of high NRR and a strong CS team was something we were preaching and doing deep dives on since well before it was well understood. Especially the power of it leading to second order revenue, from upgrades to referrals to word of mouth and more: CLTV Isn’t The Whole Story.

AI 176

AI Onboarding Customer Success Scale 176

SaaStr

MAY 27, 2025

Dear SaaStr: How Long Should I Wait to Follow Up After A Big Customer Pitch? You shouldnt wait at all. Follow upimmediatelyafter the initial pitch meeting. Ideally, within the same day. The best always do. If you cant do it that quickly, make sure its no later than 24 hours. Heres why: 1. Momentum Matters After a pitch meeting, the clients interest is at its peak.

Onboarding 125

Onboarding Sales Business 125

SaaStr

MAY 26, 2025

We’ve already seen something happen in support. You can’t automate 100% of support with AI yet. At least, not reliably. But you can automate 30%-40% of support for real … with top 10% CSAT. So what does that mean for inside sales? Probably something similar by 2026. A 50/50 Sales Team. 50% of your team are humans. 50% are AI. At least for SMB and more routine mid-market sales.

Scale 249

Scale Sales Hiring AI Sales 249

SaaStr

MAY 25, 2025

Top Posts You May Have Missed: #1. The Great AI Reset: Its Time to Refound Your Start-Up. Now. #2. OpenAI to Hit $12.7 Billion in Revenue This Year. But Wont Be Profitable Until $125 Billion in Revenue #3. The 250,000 Customer Club: How HubSpot and Monday Both Created SMB+ Empires #4. The Bar Today for a Series B #5. Dear SaaStr: How Do I Become a Great Sales Rep?

AI 242

AI SMB Revenue Startup 242

SaaStr

MAY 25, 2025

So I’m mostly made good investing decisions. My first VC investments were Pipedrive ($1.5B cash exit to Vista), Algolia (IPO candidate), Talkdesk ($10B last round, IPO candidate), Salesloft ($2.3B cash exit to Vista). And I have a few rocketships in the next batch, from Gorgias to RevenueCat to $1B+ Owner and more. A huge congrats to @RevenueCat to adding $50m at a big valuation increase to its Series C!

Investment 144

Investment New CTO CTO ChatGPT 144

SaaStr

MAY 25, 2025

Dear SaaStr: We Have a Ton of VC Interest But Are Profitable. Should We Still Raise? Summary thoughts: Yes, if your balance sheet is weak. Yes, if your gut tells you you need it. Not just want it. But — Probably No if your balance sheet is strong and you’re not sure where to deploy it. Many founders end up regretting taking capital they didn’t need in the end.

Sales Hiring 239

Sales Hiring Scale Banking Scaling 239

SaaStr

MAY 24, 2025

Top 10 Strategies Toasts CRO Uses to Crush Sales Quotas So a little while ago Toasts CRO Jonathan Vassil joined Sam Blond on SaaStr CRO Confidential on how Toast built one of the strongest but toughest rocketship in sales: a lower gross margin, lower ACV ($10k), sales-led SMB sales motion. 5 Interesting Learnings from Toast at $1.1 Billion in ARR The company now serves approximately 85,000 customers and 140,000 locations using Toast across the US, Canada, and the UK, and has reached over a billi

Strategy 144

Strategy Payment Solutions Payment Methods SMB 144

SaaStr

MAY 24, 2025

Dear SaaStr: Were At $3m ARR Growing 35%. What Does The Future Look Like? 1. Its going to be a grind. At 35% growth, youll likely double ARR every 2-3 years. That means you could hit $6M ARR in 2 years and importantly, $12M ARR in 4-5 years. While this isnt hypergrowth, its steady. If you can maintain this pace and improve your metrics (like NRR and sales efficiency), you could still build a significant, valuable B2B business over time.

Sales Hiring 201

Sales Hiring B2B Churn Retention 201

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. And more importantly, revenue and user growth that is accelerating at scale.

Payments 287

Payments Payment Solutions Underperforming Technical Team Payment Methods 287

SaaStr

MAY 23, 2025

Dear SaaStr: What Is It Like After Your Startup is Acquired? Its different. Go into it knowing that, clearly. Its not yours anymore. Post-acquisition life is a whole new world for a founder. Its not just about the money or the dealits about adjusting to a different pace, different pressures, and a different role. Heres what Ive learned from my own experience selling EchoSign to Adobe and watching other founders go through it: The Pressure Changes : The insane founder-CEO pressure youve lived wi

Startup 144

Startup Scale Acquisition Leadership 144

SaaStr

MAY 21, 2025

So there’s the 10x ARR club … hard enough today in B2B and SaaS for public companies. And then there is Palantir. By far the most highly valued B2B software company. 78x ARR as we write this! Why? It’s just a powerhouse right now: $3.5 Billion ARR Growing a stunning 39% (!) … and accelerating (!) Fueled by AI demand, it closed 139 $1B+ deals last quarter … And 31 $10M+ deals … in just 1 quarter And … it’s raining cash. 24% GAAP profit margins!

Artificial Intelligence 157

Artificial Intelligence Government AI Benchmarks 157

SaaStr

MAY 21, 2025

Dear SaaStr: How Do I Become a Great Sales Rep? To become a great sales rep, you need to focus on a few key principles and habits that separate the top performers from the rest: 1. Truly Solve Problems, Dont Just Sell The best sales reps dont just pitch productsthey solve problems. Start every conversation with a version of, How can I help you [achieve X]?

Sales 177

Sales Enterprise Business 177

SaaStr

MAY 20, 2025

So in any interesting bit of convergent evolution, both Monday and HubSpot have now passed 250,000 customers. Both started SMB (Monday even more so), and Both have now gone more enterprise (Monday even more) But still with the vast majority of their customers SMB. Both have also evolved from different roots (marketing for HubSpot, team management for Monday) to now have CRMs as their core.

SMB 280

SMB Scale Education AI 280

SaaStr

MAY 19, 2025

We’ll do deep dives on all the SaaStr + AI Summit 2025 speakers soon! We wanted to kick it off with some of the key insights with Box CEO Aaron Levie and IBM VP AI Raj Datta: The Numbers Don’t Lie – ChatGPT Hit 500M Users in Just ~2 Years Let’s start with the cold, hard metrics that SaaS leaders seem to underestimate: AI adoption is happening at an unprecedented velocity.

AI 215

AI Technology ChatGPT Cloud 215

SaaStr

MAY 19, 2025

Is your B2B startup now part of the past … because it was founded before 2023? Maybe. Be honest. Has growth slowed while new AI entrants in your space are growting at epic rates? No one’s coming to save you. But … but … it’s too late to refound your start-up in the Age of AI. It’s not too late. We are early. [link] — Akshay Krishnaswamy (@hyperindexed) May 5, 2025 The Pre-AI Stigma Is Real If you founded your SaaS company before 2023, you’re wearin

AI Search 189

AI Search AI ChatGPT Innovation 189

SaaStr

MAY 19, 2025

Dear SaaStr: We’re Thinking of Bringing in an Outside CEO to Help Us Scale. How Much Should We Pay Them? First, before you go down this path — are you sure? 90% of SaaS companies that IPO … IPO with the founder as CEO. That data here: SaaS CEOs That Go The Distance, To IPO … Tend To Be Founder-CEOs (Updated) Are you sure the better answer isn’t to go find a great VP or two to help you scale?

Scaling 177

Scaling Compensation Retention Startup 177

SaaStr

MAY 18, 2025

So a little while ago we did a very deep dive with Brian Halligan, co-founder and chair of HubSpot. One of the topics we did a deep dive on was mergers & acquisitions, and it was so good I wanted to just break out that portion of the convo: Net Net: Acquisition offers are far less common than you think. Despite HubSpot’s success, Brian Halligan reveals they “didn’t get any acquisition offers” in 18 years.

Technical Review 176

Technical Review CTO Hire CTO Sales Hiring 176

SaaStr

MAY 18, 2025

Dear SaaStr: How Should I Specialize My Sales Team? One thing is clear: most founders and VPs of Sales and CROs look back and wish they’d specialized their sales team earlier. And not have everyone work in a round-robin or similar format on all the leads, just split across their reps. You should split your AE team based on what will drive the most efficiency and results for your specific business.

Scale 163

Scale Sales Healthcare SMB 163

SaaStr

MAY 16, 2025

Dear SaaStr: We Have a $7m ARR Business But Our CAC is Way Too High. Should We Cut and Marketing To The Bone? Look don’t throw money away on sales & marketing. If your sales team can’t close anything , you need to part ways. If you are doing intiatives in marketing and they are bringing in zero customers, just stop those things. But more often, sales and marketing is closing some deals, just not enough.

Marketing 163

Marketing Scale Churn Content Marketing 163

SaaStr

MAY 16, 2025

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

Investment 177

Investment Startup Communication Engagement 177

SaaStr

MAY 13, 2025

So this is a seemingly simple post, but it’s a point I find many founders, CROs, CMOs and more get wrong. I got it wrong for a while too, until I started invest in and working with more vertical SaaS companies. And that is something somewhat counterintuitive: It may be easier to sell your second product to new customers than your existing ones.

SMB 209

SMB Engineering Branding Investment 209

SaaStr

MAY 13, 2025

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.

Outsourcing Services 195

Outsourcing Services Outsourced Development Enterprise Pricing 195

SaaStr

MAY 11, 2025

So far for SaaStr + AI Summit 2025, May 13-15, we have 711 VCs coming from 298 unique VC firms. A lot of VCs register … a bit late … so we should hit almost 800 by the time SaaStr 2025 is in full swing. Some of the notable VC firms on the list include Accel, A16Z, Base10 Partners, Emergence Capital, ICONIQ Growth, Innovation Endeavors, Mayfield, Redpoint Ventures, and Softbank, among many others.

Venture Capital 177

Venture Capital Technical Review Innovation AI 177

SaaStr

MAY 11, 2025

Dear SaaStr: How Do I Become a Better SDR? To become a better SDR, you need to focus on three key areas: precision, persistence, and value-add. Heres how you can level up: Stop Spraying and Praying : The era of blasting 10,000 generic emails is mostly over. Even with AI. Instead, focus on quality over quantity. Target 50 great prospects a week and make your outreach personalized and thoughtful.

Scale 148

Scale AI Churn Investment 148

SaaStr

MAY 10, 2025

We’re almost there! 2025 SaaStr Annual + AI Summit is THIS WEEK, May 13-15 in SF Bay!! Here are 20 Fun Things to Do at SaaStr 2025: 1. Explore the SaaStr AI Summit. This year, the SaaStr AI Summit is taking over two stages, featuring 100+ top AI startups demoing their products live. We’ve also got 20 of the top AI Ycombinator start-ups in a special demo pavillion.

AI 209

AI B2B Startup Interviewing 209

SaaStr

MAY 10, 2025

Dear SaaStr: What Is the Playbook for a Successful Customer Success Team? A good playbook for customer success is all about driving retention, expansion, and customer happiness while making it scalable: Hire Truly Product-Savvy Customer Success Managers at First Focus on hiring people who customer-focused product nerds to start. They need to just love your product, and know how to deal with its issues and solve them.

Sales Hiring 236

Sales Hiring Customer Success Scale Retention 236

SaaStr

MAY 9, 2025

SaaStr Annual + AI Summit 2025 is just around the corner , taking place at the San Mateo County Event Center from May 13-15, 2025. This comprehensive guide will help you navigate this expansive event and make the most of your experience. Event Overview & Venue The SaaStr Annual campus spans over 40 acres at the San Mateo County Event Center, featuring both indoor and outdoor spaces.

AI Search 177

AI Search AI Artificial Intelligence Transportation 177

SaaStr

MAY 9, 2025

So I’d just about given up on the second worst SaaS vendor in our stack at SaaStr. I only paid for it because literally it was a niche use case and I couldn’t find any better vendor. I hadn’t seen a feature release in years and sort of assumed they’d half given up. They cancelled their Free edition a few months back — an even worse sign of a vendor in trouble.

Social Media 177

Social Media Outsourced Development Interviewing Retention 177

SaaStr

MAY 9, 2025

Dear SaaStr: How Hard Should We Push to Get Cash Upfront in Deals? Offer it. Even make it the default for all bigger deals. But be careful in smaller ones, and where it’s not natural. In theory, collecting upfront for annual and even multi-year contracts can be a fantastic strategy, especially in the earlier days of your B2B business when cash is tight.

Payments 177

Payments Churn B2B Branding 177

SaaStr

MAY 5, 2025

Ok about 2,000 of you have already picked your 2025 SaaStr Annual + AI Summit sessions so far and here are the top sessions … for now: 1. The New Rules of SaaS Growth: Whats Next for AI, PLG, and Revenue Scale with HubSpots CEO 2. From Startup to $10B+: Lessons on Scaling, AI, and the Future of SaaS with Dropboxs Founder and CEO 3. Kick-off to SaaStr Annual 2025 with SaaStrs Founder & CEO 4.

Scale 177

Scale New CTO CTO AI 177

SaaStr

MAY 5, 2025

Dear SaaStr: Why Do Enterprise Customers Insist on Pilots? I know your sales team probably hates pilots, because in a sense, it means they have to sell the deal twice. Once for the pilot, and again to convert the pilot for a longer deal. Having an “opt out” clause after a pilot ends helps, but still, it’s a double sale. But the thing is, net net it might be less work.

Enterprise 243

Enterprise Leadership Investment Metrics 243

SaaStr

MAY 4, 2025

Dear SaaStr: How will Ai Change Sales in The Next 12 Months? Within a year, an AI sales rep will join every human sales rep on every Zoom and call 95% of I dont knows and Uh Ill get back to you will be gone Within a year, an AI BDR will answer all inbound sales questions 98% of humans setting up appointments with AEs will be — Jason SaaStr 2025 is May 13-15 Lemkin (@jasonlk) April 20, 2025 AI is going to fundamentally reshape sales over the next 12 months, and were already seeing the earl

AI 163

AI Scale Sales SMB 163

SaaStr

MAY 4, 2025

Top Posts: #1. 10 Ways AI Will Change Sales Forever. Its Already Happening, In Fact. #2. The #1 Thing That Makes Enterprise Customers See Value: A Great Dashboard #3. 20VC + SaaStr: The Hidden Game of Silicon Valley: Decoding Venture Capitals New Rules #4. The Official SaaStr Annual 2025 Party Guide: Official, Semi-Official and Unofficial Parties and Side Events!!

AI 274

AI Venture Capital Sales B2B 274

SaaStr

MAY 3, 2025

So our own SaaStr AI has now logged over 30,000 conversations (!) — and it’s pretty awesome. You can try it right here below embedded in this post, or just click here. It can answers tons of questions, from how to hire a VP of Sales and where and whom to meet at SaaStr Annual. But it can also do some pretty epic things you might not think about.

Sales Hiring 161

Sales Hiring AI Interviewing B2B 161

SaaStr

MAY 3, 2025

Dear SaaStr: From 0 to $10m ARR, At What Point Do We Start Hiring and Whom? From 0 t o $ 10M ARR, the hiring roadmap is critical because every hire has a disproportionate impact on your trajectory. Heres how Id break it down: 0 t o $ 1M ARR: Founder-Led Everything Sales : Founders should lead sales. You need to be in the trenches, hearing objections, refining the pitch, and closing deals.

Sales Hiring 250

Sales Hiring Part-Time VPE CTO Hire Scale 250

SaaStr

MAY 1, 2025

Your first few sales reps have to be … different. A bit of a product savant. A passion for the product and space that almost doesn’t make sense. And someone you can trust with your few, precious leads. "That early sales team … they have to be product gurus. They have to be product experts" @lennysan + @jasonlk pic.twitter.com/kWdOBxtnjz — Jason SaaStr 2025 is May 13-15 Lemkin (@jasonlk) May 23, 2024 Here’s a checklist to get it right: 1.

Sales Hiring 266

Sales Hiring Scale Sales Interviewing 266

SaaStr

MAY 1, 2025

Dear SaaStr: How Do I Write a Great Cold Email To VCs? If youre going to cold email SaaStr Fund or any VCyou need to make it amazing. Startups I invested in from cold email from founder: Salesloft (exited $2.4B) Talkdesk ($10B) Pipedrive (exited $1.5B) Logikcull (exited $270m) Owner Mangomint etc. I mean it can work Take your shot. Just make it great. — Jason SaaStr 2025 is May 13-15 Lemkin (@jasonlk) December 2, 2024 A great cold email can absolutely work, and does work.

Scale 162

Scale Startup Investment Scaling 162