May, 2025

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Dear SaaStr: Why Do Enterprise Customers Insist on Pilots?

SaaStr

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.

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How To Build a Convincing Opt In Popup That Gets Signups

The Daily Egg

Everyone complains about popups. But if you are trying to grow your business, who cares? Opt in popups work. The right offer, shown at the. The post How To Build a Convincing Opt In Popup That Gets Signups appeared first on The Daily Egg.

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Prepaid Card Issuing vs. Traditional Payout Methods

USIO

The way businesses pay vendors, employees, gig workers, and customers is changing fast. And prepaid card issuing is leading the charge. If your business still leans on traditional payout methods like paper checks or manual ACH, it’s time to consider what you might be missing. Lets explore how prepaid card issuing stacks up against traditional payoutsand what makes the most sense for your business.

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Clouded Judgement 5.16.25 - Net New ARR Trends

Clouded Judgement

Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Subscribe now Net New ARR Trends We’re about halfway through Q1 ‘25 earnings season. As you all know, one of my favorite metrics to look at is net new ARR added in a quarter. For some public companies, they disclose ARR.

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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.

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What Comes After the SDR Role?

Predictable Revenue

AI now does research, flags signals, and drafts emails. Freeing you to focus on what moves pipeline: creativity, personalization, and timing. The post What Comes After the SDR Role? appeared first on Predictable Revenue.

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From 0 to $10m ARR, At What Point Do We Start Hiring and Whom?

SaaStr

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.

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Credit Card Merchant Services: What to Look for (and What Most Businesses Miss)

Stax

Credit card merchant services are often viewed as a back-office function or necessary cost. And while its true that they involve fees and backend setup, thats only part of the story. When leveraged strategically, these services can become a key driver of business growth. With the right provider, merchant services can improve your checkout experience, increase cash flow, and unlock valuable business insights.

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How Embedded Payment Solutions Support Faster Digital Disbursements

USIO

Delayed payments dont just slow down your operationsthey strain vendor relationships, frustrate customers, and stall growth. The fix? Fintech Payment Solutions built to make digital disbursements faster, smarter, and easier to manage. Lets break down how these tools are transforming the way businesses move money and why its time to leave slow disbursements in the past.

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Facebook Ad Specs + Image Sizes — Fully Updated for 2025

Buffer Resources

You're spoiled for choice when it comes to Facebook ads — from images and videos to carousels and collections, there’s a format (and placement) for just about every goal. Advertising on Facebook also gives you the chance to experiment and find just the right approach for your brand.  But with so many options, it’s important to keep up with the latest Facebook ad specs.

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Mastering Apache Airflow® 3.0: What’s New (and What’s Next) for Data Orchestration

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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“All Models Are Wrong, Some Are Useful.”

Kellblog

“I have a map of the United States … actual size. It says, Scale: 1 mile = 1 mile. I spent last summer folding it. I also have a full-size map of the world. I hardly ever unroll it.” — Stephen Wright (comedian) Much as we build maps as models of the physical world, we build mathematical models all the time in the business world.

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Say Hello to Your MozCon 2025 Speaker Lineup (So Far!)

The Moz Blog

MozCon is hitting the road in 2025 with two incredible events! Join us in London (August 12) or New York (November 6) to learn from industry leaders like Lidia Infante, Andy Chadwick, Wil Reynolds, and Lily Ray. Our speaker lineup spans technical SEO, AI content systems, creative PR, and community leadership. Delivering fresh insights and strategies you can implement immediately.

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A 10 Point Checklist for Hiring Your First Few Sales Reps

SaaStr

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.

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Need to Know | Embedded Finance Unlocks Value for Underserved Small Business Sectors

Stax

The rapid evolution of embedded payments is reshaping industries and unlocking new opportunities, particularly for small business sectors that have often been overlooked. Adam Gray , Chief Transformation Officer at Stax, recently sat down with Hal Levey of PYMNTS to discuss emerging trends in payment processing and vertical integration. By enabling more tailored solutions, streamlining operations, and addressing vital concerns like fraud and security, embedded finance is becoming a crucial driv

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Agent Tooling: Connecting AI to Your Tools, Systems & Data

Speaker: Alex Salazar, CEO & Co-Founder @ Arcade | Nate Barbettini, Founding Engineer @ Arcade | Tony Karrer, Founder & CTO @ Aggregage

There’s a lot of noise surrounding the ability of AI agents to connect to your tools, systems and data. But building an AI application into a reliable, secure workflow agent isn’t as simple as plugging in an API. As an engineering leader, it can be challenging to make sense of this evolving landscape, but agent tooling provides such high value that it’s critical we figure out how to move forward.

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Glossary of Advanced Embedded Finance Terminology

USIO

Whether youre a product leader, fintech founder, or payments partner, understanding the language behind embedded finance platforms is mission-critical. This blog post is your jargon-free guide to all the advanced embedded finance terminology you’ll encounterfrom OAuth to multi-rail payment strategies. Weve organized everything alphabetically , so you can find what you need fast.

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12 Social Media Metrics You Should Be Tracking (And Why)

Buffer Resources

More doesn’t necessarily mean better. Think emails in your inbox, glitter on a Mother’s Day card, hot sauce… That applies to social media metrics, too.  You might be surprised to hear it. The more information you have, the better you can tailor your social media strategy, right? Well, not exactly. Not all social media metrics are created equal, and which ones to focus on comes down to your specific social media goals.

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The AI messaging pivot happening across SaaS

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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The Impact of AI on Education & What It Means for Work

Tom Tunguz

The blocky charts. The ability to solve a hard test problem. The hidden game of Snake. My graphing calculator was a 7th grade miracle. AI is this generation’s graphing calculator. With about 2 years’ of studies, we can draw some conclusions on its impact. A meta-analysis published in Nature showed a medium to large impact on students. ChatGPT’s Select Impact on Higher-Order Thinking Condition/Scenario Effect Size 1 Significance (p-value) Overall Effect 0.457 < 0.001 Type of

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State of AI in Sales & Marketing 2025

AI adoption is reshaping sales and marketing. But is it delivering real results? We surveyed 1,000+ GTM professionals to find out. The data is clear: AI users report 47% higher productivity and an average of 12 hours saved per week. But leaders say mainstream AI tools still fall short on accuracy and business impact. Download the full report today to see how AI is being used — and where go-to-market professionals think there are gaps and opportunities.

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Dear SaaStr: Our Biggest Potential Customers Are All Asking for Custom Features. When Do We Say Yes?

SaaStr

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.

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Three Ways To Get Fired as CEO

Kellblog

While I could write the equivalent of 50 Ways to Leave Your Lover when it comes to variations on how to get fired as CEO, the purpose of this post is simply to discuss three things CEOs can say to their boards that will perk their ears and get them to start asking questions that could lead to the CEO’s termination. Here are those three things: “ I’m getting tired of running the company.” “ I’m running out of ideas for how to fix our core problems.” ̶

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Overwhelmed IT team? How to scale without adding headcount

BetterCloud

Every IT team is grappling with the same reality: the ever-widening chasm between the demands placed on IT and the resources at their disposal. The stark figure of a 1:108 IT-to-employee ratio isnt just a statistic, its a daily challenge impacting our teams capacity, our ability to innovate, and ultimately, our contribution to the businesss strategic goals.

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How to protect GRR more effectively as a customer leader

ChurnZero

Sarah Kiley is chief sales officer at ChurnZero. With growth rates slowing and investors demanding profitability and efficiency, its no surprise that companies are being judged not only by how fast they grow, but even more critically by how well they retain. This is why gross revenue retention (GRR) is a top metric for SaaS boards in 2025. In fact, GRR isnt just a metricits a multiplier.

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5 Ways to Improve Revenue from Integrated Payments

Speaker: Pete Uselman, Director of Partner Experience at Wind River Payments

Most integrated payments providers share a percent of the payment revenue with their software partners. But, oftentimes, that revenue share is only a fraction of the true income potential software providers can realize. If you want to maximize income opportunities from your payments program, check out Wind River Payments’ webinar-on-demand.

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ZoomInfo Just Changed Its Ticker to $GTM – Here’s Why That Matters

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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RFP vs. Security Questionnaires: Key Differences and When to Use Each in Vendor Assessments

Scytale

Working with third-party vendors isnt just common – its practically inevitable, especially as your business scales. But as youre probably aware by now, with great partnerships come great responsibilities (and risks). Even if your own security posture is rock solid, your compliance and GRC efforts can still fall apart if your vendors dont hold up their end of the bargain.

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It May Be Easier to Sell a Second Product to New Customers, Not Existing Ones

SaaStr

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.

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A CEO’s High-Level Guide to GTM Troubleshooting

Kellblog

I’ve written about this topic a lot over the years, but never before integrated my ideas into a single high-level piece that not only provides a solution to the problem, but also derives it from first principles. That’s what I’ll do today. If you’re new to this topic, I strongly recommend reading the articles I link to throughout the post.

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SaaS Essentials: Failed Payment Solution Guide

For SaaS businesses, improving retention is one of the easiest and most effective ways to drive revenue and profits. With a clear link between failed payments and customer churn, having a robust failed payment recovery solution isn’t optional—it’s essential. Achieving your retention goals starts with the right solution.

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Audit-Proof IT: Building a GASB-Compliant Internal Billing System

Blulogix

By BluLogix Team Audit-Proof IT: Building a GASB-Compliant Internal Billing System In government and higher education, IT spending isnt just about efficiencyits about accountability. CIOs and IT finance leaders are expected to track every dollar, justify every allocation, and survive every audit. But many are still relying on spreadsheets and outdated tools that werent designed for todays IT complexity or compliance demands.

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Should you buy or build your customer success platform?

ChurnZero

It’s the ultimate technology dilemma for customer teams and the execs who control budgets: should you buy or build your customer success platform? When presenting a business case for a customer success platform, you can expect this to be the primary objection of a CEO or CFO: can we build this in our CRM instead of buying a new tool? Should you use the tools you already have to build something that will kind ofget you what youre looking for, or should you buy a tool developed for that spec

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SaaS sprawl is a rising concern for IT: Causes, challenges, and best practices

BetterCloud

After years of accelerated SaaS adoption, organizations have fallen victim to SaaS sprawl. Even with the average applications declining, SaaS sprawl still remains a concern. While SaaS sprawl isn’t new for IT teams, the landscape has dramatically shifted, particularly with the explosive emergence of AI. SaaS sprawl concerns increased by 55% State of SaaS 2025 This isnt just about managing a few extra subscriptions; its a systemic issue impacting security, compliance, and budget efficienc