Fri.Jul 11, 2025

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Dear SaaStr: What Are The Top Worries Founders Have As They Start to Scale?

SaaStr

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.

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Stop monitoring systems; start monitoring outcomes

Intercom, Inc.

When millions of conversations flow through your platform daily, reliability isn’t just a technical metric – it’s the foundation of customer trust. At Intercom, where our AI Agent Fin resolves millions of customer inquiries autonomously, reliability starts with one essential question: Can our customers do the job they’re hired us to do? This question has led us to develop what we call “heartbeat metrics” – vital signs that instantly tell us if our systems are truly serving their purp

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AI and the Bottom Line with Canva’s CCO: How They Built a $7B Enterprise Motion on 16 Billion AI Interactions

SaaStr

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.

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From Silos to Synergy: The Data Dictionary as CS Operations Key to Unifying the Customer Journey

Valuize Consulting

In a previous article, we dissected the three critical data challenges that often cripple Customer Success (CS) Operations: the security ambush, the hydra of disparate data models, and the subjectivity of customer health definitions. These aren’t just abstract problems; they are daily frustrations that undermine the incredible work CS Operations teams do, directly impacting your ability to deliver efficient processes, reliable reporting, and a truly effective Customer Success Platform (CSP

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Airflow Best Practices for ETL/ELT Pipelines

Speaker: Kenten Danas, Senior Manager, Developer Relations

ETL and ELT are some of the most common data engineering use cases, but can come with challenges like scaling, connectivity to other systems, and dynamically adapting to changing data sources. Airflow is specifically designed for moving and transforming data in ETL/ELT pipelines, and new features in Airflow 3.0 like assets, backfills, and event-driven scheduling make orchestrating ETL/ELT pipelines easier than ever!

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AI-Native GTM Teams Run 38% Leaner: The New Normal?

SaaStr

Sales isn’t going anywhere in the Age of AI. OpenAI has a big sales team, Windsurf does, Anthropic has a great one. It’s just … so many of the AI leaders seem to be doing it with less GTM headcount. Especially the next generation of them: Perplexity has scaled to 5,000 enterprise customers with just 5 sales reps. Cursor built a $400M business with what appears to be a skeleton GTM team.

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SaaStr AI App of the Week: Syllable.ai

SaaStr

The Enterprise-Grade Platform That Makes AI Voice Agents Actually Work at Scale We’re proud to announce that Syllable is returning as a partner for SaaStr Annual + AI Summit 2026 , following their tremendous success and impact at our 2025 event. The Bottom Line: Syllable.ai is the first enterprise-grade platform that lets you build, deploy, and manage production-ready AI voice agents without the complexity.

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Where to be: The must-attend events for customer revenue leaders in the second half of 2025

ChurnZero

Quick Summary: Customer success events in 2025 are back in full force, with top picks covering AI innovation, GTM strategy, and post-sale growth. This guide breaks down the most impactful conferences for CS leaders to prioritize based on goals, budgets, and cross-functional alignment. In-person events are officially back, and not surprisingly, CS is leading the charge.

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Anthropic May Never Catch OpenAI. But It’s Already 40% as Big.

SaaStr

Anthropic is ~40% as big as OpenAI by ARR, despite its consumer app Claude being just 5% the size of ChatGPT. The AI race isn’t just about who has the most users—it’s about who can monetize their technology most effectively. While OpenAI dominates headlines with ChatGPT’s viral success, Anthropic has quietly built a business that’s already 40% the size of OpenAI’s revenue, despite having a fraction of the consumer awareness.

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5 different paths to launch AI agents (with examples)

Sales Hacker

Hello and welcome to The GTM Newsletter by GTMnow – read by 50,000+ to scale their companies and careers. GTMnow shares insight around the go-to-market strategies responsible for explosive company growth. GTMnow highlights the strategies, along with the stories from the top 1% of GTM executives, VCs, and founders behind these strategies and companies.

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Build the Case: Quantify the Real Costs of In-House Testing and QA Gaps

Underinvesting in software testing costs more than you think, and now you can prove it. This guide helps you quantify hidden costs like developer time, support overhead, tech debt, and lost revenue. Use the companion calculator to model your own data, and present your findings with a ready-to-edit presentation template. Whether you're making the case to leadership or validating outsourcing, this toolkit gives you the numbers and tools you need.

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Cursor: Our Users Love Per Seat Pricing. It’s Just The Cost Side Makes It Harder.

SaaStr

Per seat pricing is hardly dead in the age of AI. In fact, it’s driving the $1B+ vibe coding revoltion. But the AI tooling industry just hit its first major pricing bump. Cursor’s June 2025 pricing adjustments to charge power users more on a variable / token basis —and the subsequent developer pushback—have exposed the fundamental economic tensions in how AI-powered software companies think about monetization.

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Using User Personas to Boost Performance

Neil Patel

Many marketers have great content strategies, but their campaigns don’t move the needle because they’re not speaking to the right people. If you want content that connects and converts, you need to know exactly who you’re talking to and what they care about. That’s where a strong user persona comes in. When done right, user personas help you create content that feels like a one-on-one conversation with your ideal customer.

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We Thought These Leads Were Dead. Our AI Proved Us Wrong (And Booked 4 Meetings in 48 Hours)

SaaStr

When AI Resurrects “Dead” Leads: A SaaStr Case Study on What Sales Teams Miss, But AI Can Catch Our sales AI reactivated 4 leads in past 48 hours that our human sales team said were dead / not-interested All took a meeting asap Something to reflect on — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) June 25, 2025 Last week, we experienced something that made us question everything about lead qualification.

AI
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Instagram Just Became a Search Engine

Sales Hacker

This week, Instagram made a major move that changes how your content gets discovered. For the first time, Instagram posts from public Business and Creator accounts are now being indexed by Google and Bing. That means your Reels, captions, images, alt text, and hashtags can now appear in search engine results. Why this is a big deal Until now, Instagram lived in a walled garden.

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What’s New in Apache Airflow® 3.0—And How Will It Reshape Your Data Workflows?

Speaker: Tamara Fingerlin, Developer Advocate

Apache Airflow® 3.0, the most anticipated Airflow release yet, officially launched this April. As the de facto standard for data orchestration, Airflow is trusted by over 77,000 organizations to power everything from advanced analytics to production AI and MLOps. With the 3.0 release, the top-requested features from the community were delivered, including a revamped UI for easier navigation, stronger security, and greater flexibility to run tasks anywhere at any time.

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Micro vs. Macro Conversions: What They Are and When to Use Them

The Daily Egg

Jumping into the nitty-gritty of your micro-conversions can lead to stronger macro-conversions over time. Micro- and macro-conversions differ in several major ways, including their end. The post Micro vs. Macro Conversions: What They Are and When to Use Them appeared first on The Daily Egg.

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Usio: Leading the Future of Incentives and Rewards

USIO

Let’s be honest—when it comes to rewards, people don’t want branded mugs or “points” they’ll never redeem. They want something real. Something immediate. Something that feels like cash in their pocket. And that’s exactly why Usio’s Card Issuing and program management platform are redefining how organizations handle incentives, rewards, and disbursements.

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What's New in AI Search? Whiteboard Friday Revisited With Garrett Sussman

The Moz Blog

This week, Jo is joined by Garrett Sussman as they look back on 12 months of AI Overviews and talk about Google AI Mode, query fan-out, AI search in e-commerce, local SEO, and where we stand on the age-old "Is SEO Dead?" debate.

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How We Plan Retreats, After Hosting 14 over 12+ Years (+ Get Our Retreat Planning Playbook!)

Buffer Resources

At Buffer, we're a fully remote and distributed team, which means that for most weeks of the year, we work together across 21 different countries and 49 cities. For one glorious and cherished week a year, we meet together in person for a working week we call “Retreat” to collaborate and connect. We recently wrapped up Buffer's 14th Retreat in Antalya, Türkiye!

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Struggling to Scale Test Coverage Under Pressure?

When test coverage falls behind release velocity, quality suffers, and your team feels the consequences. This guide outlines when it makes sense to outsource quality assurance (QA), the risks to watch for, and how to scale testing without increasing headcount or slowing down engineering. You will learn how leading teams are leveraging external QA partners to expand coverage, enhance defect detection, and remain aligned with CI/CD timelines.