Higher Engineer Output Expands Roadmaps, Fuels Competition
This is the question every software company is asking themselves right now. What happens to our roadmap if an engineer can produce 2X or 5X more output. The general direction will be roadmap expansion. Companies that just use this leverage to cut costs will be outcompeted by those that decide to do more. As a result, this will mean we will see more competitive battles between companies, but also the expansion of many more categories since software can touch more surface area. The limiter then becomes how rapidly your customers can actually adopt new software, how good you make that software (vs. it becomes slop because it’s so much easier), and whether you can get paid for more software or if customers’ expectations just go up over time for what they get from each vendor. As an aside, building up a brand, ecosystem, and distribution moat ends up being critical. If software development cost per unit go down, then the new game is how you can get customers to adopt and remain sticky. GTM becomes a critical factor in all this.
Front‑load Hard Work Now, Reap Freedom Later
Underrated life advice: Front-load your life with painful stuff. When you're young, work as hard as possible to acquire skills that will never go out of style. As you get a little older, use those skills to build something meaningful....
AI Clinches $100k Deal Solo From Ignored Leads
"Our AI closed a $100k deal on its own on a Saturday night." How does SaaStr use @salesforce Agentforce? "We started with the leads humans didn't want to follow up with." @tbpn @johncoogan @jordihays https://t.co/eHARBjeeih
AI‑Powered GTM Replaces Outbound, Cold Email
Outbound is broken. Cold email is dying. The B2B companies winning right now have completely rebuilt their GTM around AI. At SaaStr AI 2026, they're showing you exactly how. May 12-14. SF Bay. https://t.co/K2JIAOSqol
Great Agents Matter; AI Just Jump‑starts Resolutions
This is what folks miss in AI CX. Even if the AI can’t resolve a complex issue, folks still love a great agent that is well trained. It can at least get a resolution kicked off, almost instantly.
Demand Generation Beats Brand: Master Lead Magnets Now
Forget what the gurus say. Real B2B marketers know the truth. Most B2B Marketers are told to just post content, build a brand, and pray that leads follow. But after years in the trenches with clients, I’ve seen a brutal...
Stop Settling: Build Fast, Solve Big Pain, Hire Sparingly
10 things I’d tell founders if I weren’t afraid of hurting their feelings 👇 1. "Slightly better" is a death sentence. You can grind your way to a decent business, but breakout growth is off the table. Users need to...
Early Hires Need Passion, Later Scaling Can Diversify
Not everyone on the team really needs to be on your mission But almost all the first 50 employees do Hire pirates and romantics at least until you are truly ready to scale
Create Buy-In Conditions, Not Just Sales Pitches
Stop selling and start creating the conditions for buy-in. That’s the advice of Howie Chan , who recently hosted me on his Influence Anyone podcast. It sounds like a smart strategy. But exactly how do you make it happen? Howie...
Brand Is a Performance Lever, Not Just Aesthetics
Most brands treat “brand” like decoration. Colors, fonts, or a silly mood board someone approved once and never revisited. Then they wonder why performance gets more expensive every quarter. This happens when brand is viewed as aesthetic instead of infrastructure....
AI Search Shifts Focus From Clicks to Late‑Funnel Leads
Yep. AEO/GEO/SEO/WWJD/IMO/YOLO... AI search is important and there is no better team in the game than Docebo. Last year, Kyle Poyar interviewed Silvia Valencia and Valeriia Frolova about how to actually think about AI search, and I believe it's still...
Humans Still Needed to Orchestrate AI Agents
"For now, humans have to manage the AI Agents. Meta agents aren't there yet in AI GTM. The orchestration has to be you." with @kylecnorton CRO @owner https://t.co/k1ML07ypMJ
AI Lets You Stay Small when Talent Is Scarce
"If you can magically find 10 great humans to cost-effectively do the work, sure, don't use AI" @tbpn with @johncoogan + @jordihays. "But easier said than done." "AI also gives you control. To hire the number of humans you...
Ignore Noise, Leverage Your Skill, Land First Customer
The longer you focus on all the BS? The longer you're distracted. Quit paying attention to the noise, hatred, anger, divisiveness, outrage, media circus, and all of the other nonsense. Shut that stuff down. Then follow this plan: - Pick...
Short-Term Pipeline Pressure Stifles Long-Term Brand Differentiation
You can't solve differentiation with a 30-day deadline. Everyone knows brand matters. No one has the time (or permission) to build it. We surveyed 50 mid-market B2B marketing leaders. The data reveals a massive trap: 44% say standing out in a crowded...
Stop Saving Customers; Earn Their Loyalty Continuously
Your "save" playbook is a crutch. Your win-back sequence is a safety net. And they're both giving you permission to fail your customers. What would you do differently now if you weren't allowed to fix it later? No save motion...
AI Agent Replaces Staff, Drives $100M ARR in 24 Months
This AI company hit $100M ARR in under 24 months by making a crazy bet on AI agents most startups ignored👇 At the end of 2023, Podium already had 60,000+ SMB customers using the product to manage leads and customer...
Lightweight Rivals Can Swiftly Become Major Threats
Competitors can go from a nuisance to a viable threat much more quickly than many brands realize, and by the time it's impacting the sales conversations it can be much harder to address. For market leaders, especially ones who have...
AI Revolutionizes Customer Research: Human Insight Still Essential
I wrapped up Season 5 of Building With Buyers , but then this convo was TOO GOOD + too relevant so then I un-wrapped up Season 5 😂 at least for a bit Caitlin Sullivan joined me to talk about...
Avoid the $50M ARR Plateau with Early Scaling Wisdom
I’ve talked about my CEO friend who raised $100M and got stuck at $50M ARR a lot. But if I could go back to 2019 when he was at $20M, and rockets were still firing, this is exactly what I...
Delete Unfit Calls: Prioritize Picking the Right Deals
Its OK to delete sales calls from your calendar. We have an inbound GTM machine in place in every company that I've run. This means that calls get booked on our calendars by our ideal customers on a consistent basis....
Fix Conversion Rates, Not Just Lead Volume
B2B SaaS team: "We need more leads." Me: "Wait, first answer this question:" What's your conversion rate at each stage? Most of the time, they don't know, and that's the real problem that needs to be solved. More leads is...
Marketing Drives the Journey; Sales Overestimates Its Role
Salespeople, you tend to think that you're a lot more important to the customer journey than you actually are. Marketing, you have a larger part in closing deals than you probably give yourself credit for. Now, I know marketers, you're...
Skip Intros—Email Your Results Directly to SaaStr Fund
If you happen to want me to invest in you via @saastrfund, and it's a fit ... 📨Just email. Email me everything -- all the good stuff. No need for a warm intro, or any sort of intro. They just waste...
B2B AI Teams Achieve 5× Productivity as New Standard
The most impressive B2B + AI companies I'm seeing right now have 8 people doing the work of 40. That's not a flex—it's the new baseline. SaaStr AI 2026 is where you learn how they're doing it. May 12-14. SF Bay....
Reliable AI Agent Startup Delivers Seamless Setup, Wins Loyalty
There’s a leading AI Agent startup that’s wanted us to use them for a loooong time. Finally, this week, they did the work. They set it up for us. No drama, no games, they just set it up in a...
AI Turns $50K Copywork Into 20 Minutes
$50K of copywriting. 15 minutes. One prompt. That's what we did with Claude. Rewrote my agency's homepage from scratch. Friends rated the old copy 6/10. New version? 9/10. The prompt is stupidly simple: "Pull from the top 10 advertising practitioners in history. Score...
Built Our Own AI VP Marketing Using Replit Stack
We build our own AI VP Marketing on @Replit + @salesforce + @clay + @claudeai + @zapier Why? We couldn't find an AI Agent that could do it More in deep dive from SaaStr AI Day below: https://t.co/jrxnHQMwYd
Vulnerability Becomes Leaders' Superpower in AI Era
⁉️ Is vulnerability the missing piece in your AI strategy? 🦸♀️ As we integrate AI into our companies, the role of a leader is shifting. In this insightful Forbes interview, Workday CMO Emma Chalwin discusses why vulnerability is becoming a...
Clients Pay for Results, Not Hours Worked
Clients do not pay for hours. They pay for outcomes and competence. Don’t forget that.
Wrong Leaders Cost Years of Lost Potential
Picking the wrong VP reverberates for 2+ years Picking the wrong cofounder reverberates for 10+ years You don’t fail, it’s just you could have done so much more. And that compounds, too.
Stop DIY Taxes—Automate with Anrok for Scale
4 signs you should not be going it alone, tax-wise: 1. You are not, in fact, an accountant. 2. You crossed the $1M annual sales mark and your tax filings went from 2 --> 40, overnight. 3. You did not...
B2B Marketers Shift From Paid Ads to Events, Partnerships
The great paid ads pullback of 2026 is here. We surveyed 50 mid-market B2B marketing leaders with Wynter. The data is violent. 72% are actively slashing budgets for paid ads, content syndication, or agencies. This isn't a "hot take." It is a capital...
All Strategies Work—Pick One and Stop Paralyzing
Today a journalist emailed me one of those questions that looks innocent and absolutely isn’t. What unexpected opportunity came from starting your own business and what advice would you give others about recognising opportunities. Which is really asking, what did...
Attention Without Sales Means Missing the Conversion Bridge
If your content is getting attention but not buyers, you’re building interest without a bridge.
Master Your Pitch, Meet Top VCs, Secure Term Sheets
- Know your worth - Hone your pitch - Meet the best VCs - Collect term sheets That's SaaStr AI VC -> https://t.co/XzJ5d0OqGr https://t.co/qulPugatLR
Azure Hits $103B Run Rate, up 38% YoY
Azure at a ~$103B run rate growing 38% constant currency Quarterly YoY growth trends below
Prioritizing Guided Onboarding for Complex Data Platform
I spent 2025 building out the best product I could for brand and category tracking, and my current next product focus is making sure that I surround it with a strong onboarding and training experience. The double-edged sword of adding...
Leaders' Excuses Limit Teams; Ask, Don’t Assume
"The team won't do it" is rarely about them. It's about you. We were talking about having CSMs tell customers when they're getting in their own way. Not being rude. Just direct. "We can only help you if you do...
Clean Customer Data Powers Personalized LLM Responses
Tealium gives LLMs what they usually lack: real customer context. Things like cross-channel behavior, lifecycle stage, affinities, and history flow into prompts and workflows, so AI responses stop feeling generic and start feeling more like they’re written for one person....
AI‑Powered Concept Testing Eliminates Product Validation Bottleneck
The bottleneck in product development is moving towards knowing what to build. Ignoring it is going to lead to bloated products. Pre-AI it was already common to skip validation. But as execution speeds up, and you need to feed the...
Most Companies Overestimate Storytelling; New Scale Reveals Gaps
Most companies think they’re great at storytelling. That is, until they look at this… We recently created a framework called the Storytelling Maturity Scale. It rates your organization from 1 to 5 based on how well your teams can tell...
ChatGPT's Recommendations Vary Widely, Challenging Brand Tracking
NEW research: https://t.co/yE1LogIFHO If you give ChatGPT the same request for product recommendations 100X, will you ever get the same list twice? And what does that answer mean for folks who try to track their brand presence in AI tools? Finally, some real...
AI Revolutionizes Enterprise Sales and Organizational Structure
New @ThePeelPod with @JacquelineSYC19 How AI is changing data, getting enterprise customers from cold emails during YC, building an AI BDR in-house, why most functions at @artie_labs report to the CTO (not CEO), and what it's like raising a Series...
Startups Should Ditch Annual Plans for Quarterly Reset
Annual planning is one of the most over-copied “big company” rituals in startups—and it quietly creates a lot of bad decisions. In large companies, annual planning makes sense. They’re hiring hundreds (sometimes thousands) of people, mobilizing new strategies, changing systems,...
Stop Complaining, Boost Energy: Simplify Teams for 2026
Folks that complain consume about 20x the energy of those that just get sh*t done Simplify the team for 2026
Mercedes‑Teams Partnership Clashes on Brand Coherence
Mercedes is integrating Microsoft Teams into the 2026 all-new CLA Coupe. Let’s set aside the obvious safety question of video meetings while driving for a second. Here’s the thing that makes me scratch my head... Mercedes is a luxury performance...
B2B Buying Is Fueled by Fear, Not Logic
B2B has a dirty little secret: 🫣 We pretend buyers are rational. Because it's easier than admitting they're human. Here's what we say drives B2B buying decisions: ✅ ROI ✅ Feature comparisons ✅ Technical specs ✅ Business cases so logical,...
Assumption Drift, Not Execution, Undermines Growth Plans
Assumption drift kills more growth plans than bad execution. But we keep blaming execution anyway. Because assumption drift is quiet. Uncomfortable. And usually leader-owned. It looks like this: • The buyer evolves • Pricing gets “tested” • Revenue targets shift...
Joining Insight Collective to Shape Marketing's Complex Future
My belief in marketing effectiveness has only grown as I've seen the landscape getting more and more complex for marketing. Through my own journey into it, and building the Storybook platform around the learnings, it's also connected me with some...
