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This week on 20VC x SaaStr, Harry Stebbings, Rory O’Driscoll and I went through Nvidia’s $96.2B quarter and its 70% forward guide, the $12.9B Hugging Face deal, OpenAI cutting off Curso…

36 percent of B2B software companies cut sales development headcount in the last year, per Emergence Capital's survey of 560+ companies (via SaaStr). Most of that was attrition, not layoffs: open roles simply left unfilled. I led sales development for about seven years, and I think the shrinkage is mostly healthy. The high-volume, throw-more-reps-at-it model was never actually durable. You could inflate activity for a couple quarters, but the moment hiring slowed, the whole thing sagged, because output was tied to headcount instead of design. When you can always hire another rep, you never fix the system. Ramp too slow? Hire ahead of it. Reps burning out at ten months? Backfill. Every structural weakness gets a headcount patch, so none of them get solved. Take the headcount lever away, and the design problems surface all at once. The only way to grow output now is to make each rep more effective. That forces three questions teams could avoid before: Why does ramp take six months? Ramp that works is a system of checkpoints, not a week of orientation followed by a void. Why do good reps leave at month ten? A skill ladder beats an activity quota. Reps climbing a defined progression of capabilities have a reason to stay; reps hitting a dial count do not. Why does coaching not stick? A smaller team is more coachable, not less. Fewer reps means each one matters more and the ceiling on each one is higher. The companies that win this next stretch are not the ones with the most reps. They are the ones who finally designed the role. Is your team using the smaller headcount as a forcing function, or just absorbing the cut? #SDR #SalesLeadership #SalesDevelopment

The SaaStr piece on the CPOs of Harvey, Glean and Rubrik has a line that stuck with me: the old CPO job was telling the team what you'd ship this year, then quietly moving half of it to next quarter. When an investor asked for a feature, you said "coming." And eventually it came. That model is dead for anyone shipping agents, and not for the reasons vendors like to say. The hard part isn't the model. It's that agents fail differently than features. A feature either works or it doesn't. An agent works 94% of the time and the other 6% quietly books the wrong GL code or emails the wrong client. I've watched a Salesforce Einstein pilot get pulled in a bank because it summarized case notes beautifully and hallucinated the account balance twice. Two times out of hundreds. That was enough. So the roadmap game changes. You can't defer reliability to next quarter. Either the agent is trustworthy at cutover or it doesn't ship, because the failure mode isn't a missing button, it's a wrong answer nobody caught. The CPOs in that piece get this. Most enterprise buyers I sit with still don't. They're scoping agents like they scoped SuiteBilling modules. For those shipping agents into regulated workflows: what's your actual bar for "good enough" accuracy before it goes live? #EnterpriseAI #AgenticAI #ProductManagement #SaaS

Every AI case study hides one number. Not the one you're thinking of. SaaStr's 254 dollar a month AI VP of Marketing post traveled everywhere this year. The full build it yourself playbook followed in June. Cost, architecture, workflows, all public. One number was missing from both: the reversal rate. The percentage of the agent's decisions a human had to undo before they shipped. Cost tells you what you spent. Reversal rate tells you what you got. An agent that's cheap and gets overridden 40 percent of the time on its highest stakes decisions isn't automation. It's a human doing the job plus a review layer, priced like a discount. The framework I use to measure it, grouped by decision type instead of one blended average: Under 5 percent reversal: autonomous ready. 5 to 20 percent: still learning, human stays in the loop, watch the trend. Above 20 percent: not ready, no matter how much time it looks like it's saving. Running this on a lead routing agent for a fractional client this year, the blended rate looked fine. Split by decision type, standard territory routing sat under 4 percent. Anything touching a named enterprise account sat at 38 percent, because the agent had no visibility into deal context living in a rep's head. That's the gap cost per month never shows you. 2027 budget conversations are going to ask for proof, not invoices.

I'm headed Drive by Exit Five with Mona Csada in Stowe, VT, next week! ✈️ This is my first time attending Drive, but I have been to SaaStr several times as well as SaaStock. I think this one's going to be quite different and I'm very curious to experience it. 🎯 Completely B2B marketing focused 👥 Only 400 attendees ⛰️ Tucked away at a mountain resort 🥾 Networking activities include s'mores and hiking (my jam!!) 🐐 A couple of marketing goats, Ann Handley and Seth Godin are speaking! I'm attending brand, messaging, and marketing strategy sessions put on by Jess Cook, Diane Wiredu 🦁, and Ido Mart and can't wait to learn from them! 🤓 If you're headed to Drive too I'd love to connect!

The line in the SaaStr piece that stuck with me: they still pay for Salesforce, still depend on the data, they just stopped opening the UI. Six months of running it "headless" through their own Claude layer. I get the appeal. The Salesforce UI has accumulated fifteen years of tabs, related lists, and page layouts that nobody fully remembers configuring. If your team lives in Slack anyway, asking Claude "what changed on the Acme opportunity this week" beats four clicks and a report builder. But headless Salesforce isn't free. You're now the one owning field-level security in your prompt layer. Salesforce's UI enforces sharing rules, validation rules, and record-level access whether you like it or not. The moment you go API-first through an LLM, you're responsible for making sure a rep can't query pipeline they were never supposed to see. That logic lived in the platform. Now it lives in your middleware, and your auditor is going to want to see it. SaaStr is a small, technical team where this works. In a bank with 400 seats and a compliance function that reads every SOQL query, "we stopped using the UI" is a sentence that ends a meeting badly. For those who've tried API-first CRM access at scale — how did you handle sharing rules outside the UI? #Salesforce #CRM #EnterpriseAI #SystemsIntegration

The next evolution of Vertical SaaS is already happening. Look 👀 at Toast They started by solving real problems for restaurants with software. 1️⃣ then they added payments. 💵 2️⃣ then capital. 🏦 Today, fintech represents 81% of Toast’s reported revenue Now comes AI, they’re adding AI, with 40,000 locations already using Toast IQ every week. Software → Payments → Capital → AI Toast already has the customer, the data and a place inside the day to day workflow. Toast IQ can use that context to answer questions, surface opportunities and actually help operators take action. Software → Payments → Capital → AI That’s the advantage vertical SaaS companies have. They don't have to figure out where AI fits. They already understand the problems their customers are trying to solve. I think we’re going to see a lot more companies follow this path. Here's a great breakdown from SaaStr. https://lnkd.in/g-aA4PYv #VerticalSaaS #EmbeddedFinance #Fintech #Partnerships #Payments #AI #toast #saastr

Couple of interesting news pieces that tell an interesting story when put side-by-side when looking at the state of B2B sales. Yes, reading about this taught me some stuff about B2B sales. No. This isn't a meme. Yes, the image is AI generated. One: Forrester asked about 18,000 buyers where they actually get their information. 94% now use AI in the purchase process, and twice as many named genAI as their most meaningful source than named anything else. Vendor websites. Product experts. Salespeople. All of us, comfortably beaten by a chatbot. Two: Woodpecker looked at 20 million sent emails. Reply rates have slid from 5.1% in 2024 to 3.43% today. SaaStr's AI agents were each firing off 3,221 emails a month. That's roughly one every three minutes of the working day. A human SDR manages somewhere between 75 and 285, and also needs lunch. So. We built machines that can read the entire internet... and set them to work writing "Hi {FirstName}, hope this finds you well!" The AI SDR category is now churning at 50 to 70% a year, which means the robots are getting fired faster than the humans they were hired to replace. There's a lesson in there somewhere. For the record, I'm firmly pro-AI. I use it every day, and I'd hand over my CRM admin tomorrow (please, someone, take it). However, we've aimed the thing squarely at the one part of the job nobody was asking for more of. Meanwhile, your buyer turns up already briefed, already halfway to a business case, and 20% of them are quietly less sure than when they started, because some of what the AI told them was rubbish.

📣 MARKETERS — SAVE THIS LIST! I asked this community which marketing + business conferences are actually worth attending, and y’all delivered. 👇🏽 Here are some to have on your 2026–2027 calendar: 🌍 Marketing • UNBOUND (HubSpot) — Sept. 16–18, 2026 | Boston, MA 🔗 https://lnkd.in/eg8ER4gj • Content Marketing World — Oct. 5–7, 2026 | Denver, CO 🔗 https://lnkd.in/etE5BUkM • Social Media Marketing World — Apr. 1–3, 2027 | Anaheim, CA 🔗 https://lnkd.in/eET5pggq 📈 B2B / SaaS • B2B Marketing Exchange — Feb. 22–24, 2027 | Carlsbad, CA 🔗 https://lnkd.in/excmkTSR • SaaStr Annual — May 11–12, 2027 | San Francisco Bay Area, CA 🔗 https://lnkd.in/esYEmMXC 🚀 Growth / Networking • SXSW — Mar. 15–21, 2027 | Austin, TX 🔗 https://sxsw.com/ • Turing Fest — Sept. 22–23, 2026 | Edinburgh, Scotland 🔗 https://turingfest.com/ ✈️ International • Marketing Festival — Apr. 20–21, 2027 | Brno, Czech Republic 🔗 https://lnkd.in/e62swAkV Which one are you attending? 👀 And if there’s a conference every marketer should know about, drop it in the comments! 👇🏽 #Marketing #MarketingOps #B2BMarketing #DigitalMarketing #BusinessConferences #Networking

The rest of 2026 is *STACKED* for GTM + GTME conferences 👇🏼 🗺️ GTM World Tour (BetterContact) | 📆 Sept 10 |📍Paris, France ⛓️‍💥 UNBOUND (HubSpot) 📆 Sept 16-18 |📍Boston, MA 🦾 AI for GTM Summit (GTM Alliance) 📆 Sept 22-23 |📍SF 🗽 GTM2026 (Pavilion) 📆 Sept 28 - Oct 1 |📍NYC 💫 ApolloNEXT (Apollo.io) 📆 Sept 30 |📍SF 🗺️ GTM World Tour (BetterContact) 📆 Oct 1 |📍SF 🕹️ Opstars (LeanData) 📆 Oct 5-6 |📍SF 🎨 Sculpt (Clay) 📆 Oct 8 |📍SF 🛠️ Pipeline Conference (SDRLeader.com) 📆 Oct 21-23 |📍Dallas, TX 👾 SaaStr Europa (SaaStr Ai) 📆 Dec 1-2 |📍London, UK *Seven of these events are in a ~three week window in the U.S. 🇺🇸 Also pretty sweet to see Europe gaining a lot of traction every year 🌍 Most important imo: Sculpt (Krista Poth + I will be there!), ApolloNEXT (was an absolute blast last year), GTM2026 (here in NYC so will be around) Comment below if I missed any or you're attending the NYC / SF stretch and want to grab coffee ☕️ Pictured: spicy chicken parm sandwich @ Molinari's in North Beach, SF that I cannot wait to get back to... IYKYK 🔥 #GTM

New!! In The Early Days, You Won’t Have Enough Customers. But Your Mini-Brand Will Come to Your Rescue.: "You think brand doesn't matter in the early days. But it turns out, you'll have a 'mini-brand' far earlier than you might think. Often by just $2-$3m ARR. Customers in your niche, in the part of the market where you do win, will start to hear about you. Double down and… pic.twitter.com/xa6ksY6lQ5 — Jason ✨👾SaaStr.Ai✨... Continue Reading

I think we’re asking the wrong question about AI-generated code. We ask: “Does it work?” A better question is: “Would I trust this in production?” There’s a real example that makes this painfully clear. In 2025, during a public vibe-coding experiment, Replit’s AI agent deleted a live production database belonging to SaaStr founder Jason Lemkin. The database contained data on more than 1,200 executives and companies. The important part isn't “AI is deceptive.” The interesting part is what the incident exposed: The agent had access to production. Development and production weren't properly separated. A natural-language "code freeze" wasn't enough to prevent destructive actions. Replit later introduced separate development and production databases and additional safety measures. That’s the lesson I care about. AI can write the code. But you still need to review the system around that code. Before shipping an AI-built app, I’d want answers to questions like: → Can users access data they shouldn't? → What happens when the database fails? → What can the AI actually modify? → Are production and development properly isolated? → What happens when an external API times out? → Can I recover if something goes wrong? Vibe coding makes building software faster. It doesn't remove the need for engineering judgment. #vibecoding #claudecode #saas

SaaStr’s headless Salesforce bet exposes the real ops question: who owns the surface? If Salesforce is becoming backend infrastructure and your team wants Slack bots or AI agents on top, the risk isn’t architecture. It’s governance. SaaStr proved the pattern: Salesforce stays the system of record, APIs expose the data, and different people use different surfaces. Useful. But the real ops question is: who owns read/write access by surface? If you only change one thing, change this: create a surface-ownership matrix before you expand headless workflows. Run it this week Setup: list every surface touching CRM: native UI, Slack, agents, custom apps. Step 1: mark read, write, approval-trigger access. Step 2: test whether permissions, sharing rules, and field-level security behave the same via API. Step 3: flag workflows that should stay UI-first. Hypothesis: If we document and test surface ownership first, then rollout risk will drop because permission debt shows up before automation scales. Success = fewer governance gaps found post-launch. Guardrails = no broken approvals, no unauthorized writes. Trade-off: this slows rollout before it improves resilience. When this is wrong: very small teams can handle this informally. Most can’t for long. What surface in your CRM stack has write access today that nobody explicitly owns? #Salesforce #MarketingOps #RevOps #B2BSaaS

How “Headless CRM” Is Changing the Way Teams Use Salesforce SaaStr ran Salesforce without its UI for six months. Agentforce is validating the AI thesis. Read the full article → https://lnkd.in/gfivMwvs #CRMDaily #CRMNews #GTM #RevOps #Salesforce #HubSpot #SalesTech

Very interesting. Every one of Klaviyo 2300 employees had to hit L3 AI usage by June. Everyone  engineers, sales, design, marketing, support. All product managers now commit code directly. Klaviyo CEO laid out the actual ladder at SaaStr Ai, borrowed loosely from self driving car autonomy levels L1 is using AI to search for answers, L2 is running individual agent sessions to do tasks, L3 is continuously running multiple agents at once, breaking your own problems down into tasks an agent can execute. This was not a suggestion it was a mandate with a deadline. Their internal system for this is called Dark Factory, you give it a prompt, it acts as its own PM writes specs, breaks the problem into engineering subsystems, defines the API contracts between the pieces, then deploys subagents to build against those contracts. It reportedly produced their Composer agent prototype in a single weekend, running through Saturday and Sunday with a human stepping in only when requirements got ambiguous. The results composer hit 95K+ users in its first month, a 25% weekly return rate, and credit consumption growing 30% week over week. Klaviyo Q2 revenue came in at $370.6M, up 26%, with guidance raised to roughly $1.53B. Nice work I would say. They also named five specific mistakes to avoid giving agents uncontrolled access to critical systems, stopping at a working prototype without hardening it for production, shipping raw model output without domain specific feedback loops, leaving interfaces between teams ambiguous, and designing for a human UI first instead of API first. That last one especially designing for agents as the primary consumer of your product, not humans clicking through a dashboard feels like the actual thesis of the whole thing. I keep circling back to something from a couple weeks ago owner.com line that every time a customer logs in, they have failed. Klaviyo L3 mandate is the internal facing version of the same idea. It is not use AI to be faster at your job but your job now includes directing agents to do parts of it you used to do yourself for literally every role in the company, not just engineering. What I can not  tell yet is whether this becomes the standard org chart for every serious tech company in next 6-18 months, or whether it is the kind of aggressive internal mandate that only works because Klaviyo happens to have the resources and culture to pull it off without breaking things. Probably worth watching who tries to copy the L3 mandate and actually survives it.

SaaStr published a hard-truths list this month. One line stuck with me: "If growth isn't accelerating, you're not an AI company." Watch where that line actually sits. Agents on the roadmap: not an AI company. AI features shipped: not an AI company. An agent in production while growth sits at 15%: not an AI company yet. Growth bending upward because AI collapsed your cost to sell, serve, or ship: now we're talking. The market already grades on this curve. Airtable sold at 2.7x ARR against an $11.7B 2021 mark. Domo went for $400M against a $2B peak. That's what the old curve pays. A rebrand is not a strategy. Acceleration is. (The list: SaaStr x TBPN, August 2026. Receipt in the image.)

New!! To Really Scale, You Need $1M on Your Balance Sheet for Every $2M in ARR: "To really invest in your team, product, etc. you need at least $1 on the balance sheet for each $2 in ARR. At $20m ARR? You need $10m in the bank to make the hires, burn the tokens, etc. to really get to the next level. Below that … you hesitate." pic.twitter.com/Vdgzq0uKxC — Jason ✨👾SaaStr.Ai✨... Continue Reading

📍 SaaStr Annual 2021. The first big one back. It was September at San Mateo County Event Center. Money was still cheap, everything was outdoors, and booth giveaways were at an all-time high. 🎁 #swagswipers Feeling nostalgic this week, I pulled the sponsor list to see how those companies are doing after five years. My guess was that a lot of them didn't make it. I was wrong. 📊 What happened instead was absorption: 🤝 39 acquisitions 💼 13 PE buyouts 📉 Roughly 30% of the 178 sponsors are no longer independent A handful went public in the months that followed. Then IPOs from this list essentially stopped. Many of the companies that looked like candidates in 2021 are still sitting in that same category today. That's consolidation, not carnage. Very different story from the one I expected to find. Were you there in 2021? #SaaS #SaaStr #B2B #GoToMarket

For the past six-plus months, almost no one at SaaStr has logged into Salesforce. The data is all still there. We still pay for it. We still depend on it. We just stopped using the UI as the primar…

New!! Dear SaaStr: My Sales Rep is Grossly Underperforming but is Involved in a Key Deal. Should I Fire Him or Wait for The Deal to Close?: Dear SaaStr: My Sales Rep is Grossly Underperforming but is Involved in a Key Deal. Should I Fire Him or Wait for The Deal to Close? This is pretty common and most founders make the same mistake.  Move on from the rep now.  There is almost no chance he is adding value to the prospect... Continue Reading