Clouded Judgement

JUNE 17, 2025

My hope is that this analysis can provide startup entrepreneurs with a framework for how to manage their businesses around SaaS metrics (e.g., FCF Margin FCF is an important metric to evaluate in SaaS businesses. Through these interactions, I’ve built up mental benchmarks for metrics on which I place extra emphasis.

Cloud 277

Cloud Software Benchmarks Retention 277

USIO

JUNE 19, 2025

Picture this: You’re building an awesome SaaS tool—maybe for managing booster clubs (like BoosterHub) or for streamlining medical offices (like PracticeSuite). Let’s explore how SaaS companies are monetizing embedded payments, how big this opportunity really is, and what providers make it easy (and profitable). Valued at $261.1

Payments 130

Payments SaaS Payments Payment Services Payment Solutions 130

SaaStr

JUNE 4, 2025

HubSpot CEO Yamini Rangan just laid it bare at a recent conference, and it should make every SaaS leader uncomfortable. A few examples from SaaStr speakers: David Sacks (Craft Ventures, Yammer ) has talked about how, in early-stage SaaS, even with a small sales team, you often see only 50%-60% of assigned accounts getting proper follow-up.

Scale 244

Scale AI Underperforming Technical Team Sales 244

USIO

JULY 1, 2024

In the competitive world of Software as a Service (SaaS), generating recurring revenue is essential for sustainable growth. Here are three ways SaaS organizations can create recurring revenue without spending a dime. By focusing on customer satisfaction and reducing churn, SaaS companies can maintain a steady revenue stream.

Payments 306

Payments SaaS Payments Payment Solutions Payment Services 306

User Pilot

OCTOBER 10, 2024

Can you imagine what the ideal SaaS customer onboarding process looks like? That’s why we’ll go over what onboarding is in SaaS and analyze 8 onboarding examples from reputable SaaS companies to learn what they’re doing right (or wrong). SaaS customer onboarding FAQs What is SaaS customer onboarding?

Onboarding 105

Onboarding SaaS Software Communication 105

SaaStr

OCTOBER 30, 2024

1 Do reference checks Talk to as many founders they’ve invested in as you can and do reference checks. A bad investor doesn’t come off the cap table until you sell the company or years after an IPO. And so much happens in that time, in that decade or more. So here are 8 signs to help you avoid bad investors. #1

Venture Capital 306

Venture Capital Software Review Investment Startup 306

Sales Hacker

FEBRUARY 7, 2025

SaaS pricing isn’t static – it’s a living strategy that grows with your company. From your first paying customers to enterprise domination, here’s how successful SaaS companies level up their pricing game to maximize growth and profitability at every turn.

Pricing 107

Pricing Scale SaaS Technical Review 107

SaaStr

JUNE 4, 2023

A few tells: No CEO-level reference. Please, do real reference checks — and find at least one CEO or boss that says they are truly great. Reference checks are not a waste of time. But they actually aren’t that good. They didn’t really do it. They just worked there. Maybe not everywhere. Zero is an issue.

Sales Hiring 297

Sales Hiring SaaS Interviewing Startup 297

SaaStr

JANUARY 28, 2025

Proof of Concept and Early References One of the hurdles in the early days is that every customer wants to do a proof of concept (POC) that’s 100% customized, but having success cases and references can help alleviate this issue. The biggest headwinds to mass AI adoption are literacy, fear, and user experience.

AI Search 244

AI Search AI Artificial Intelligence Technical Review 244

SaaStr

JANUARY 3, 2022

One of one top engineers at Adobe Sign / EchoSign, who had strong experience both in consumer internet and enterprise internet, told me a while back the #1 reason he disliked SaaS / enterprise — it never gets easier. But one of my top learnings from to all the other SaaS start-ups out there: for the founders — it gets easier.

Scale 339

Scale Sales Hiring SaaS Engineering 339

SaaStr

SEPTEMBER 7, 2024

So one of SaaStr Fund’s latest investments is Mangomint, a vertical SaaS platform for spas and salons. There are multiple vendors in different segments, including Mindbody which IPO’d a SaaS generation ago and then taken private in a $2B Vista acquisition. And why is Vertical SaaS thriving today? Pretty cool!

SaaS Payments 306

SaaS Payments Payments Payment Methods SMB 306

SaaStr

JUNE 28, 2025

And for SaaS companies with strong fundamentals, the opportunity window is wide open. The B2B SaaS companies everyone has been waiting for are finally filing and preparing to go public: Already Filed (2025 IPOs Highly Likely) Figma – Cloud-based design platform, confidentially filed April 2025. Stop waiting.

Payments 176

Payments SaaS Payments Payment Services AI 176

SaaStr

MARCH 2, 2023

Dear SaaStr: When Do You Start to Develop a Brand in SaaS? At this point, customers start referring other customers to you. A little more here : heard good things image from here The post Dear SaaStr: When Do You Start to Develop a Brand in SaaS? In my experience, probably about $2m worth of happy customers.

Branding 278

Branding Development SaaS Investment 278

TechEmpower SaaS

DECEMBER 11, 2023

References: The company should willingly provide references. cto , product , saas Do they assist with the transition to in-house or other developers? How do they handle hosting and support? Client Retention: Do they have repeat or long-term clients? tew_cta text="Do you have an idea for a software project?

Software Development 443

Software Development Development Software Review Software 443

TechEmpower SaaS

OCTOBER 9, 2023

Structured Data refers to information organized in a defined manner, making it easier to search and analyze. Here's a suggested approach: Ground Truth Creation: Design a test dataset with established answers or recognized documents to serve as a reference point. cto , infotech , innovation , product , project , saas

AI Search 519

AI Search Artificial Intelligence Generative AI AI 519

SaaStr

OCTOBER 22, 2021

Yes, your first customers will refer you to others, get you more leads. Today the best SaaS companies are scaling faster, so you may see material results faster. My point is Viral is a Medium and Long Game in SaaS. Just plan around that for your so-called “viral” SaaS app. Absolutely. It will work.

Scale 286

Scale B2C SaaS Scaling 286

SaaStr

MARCH 23, 2025

Top-tier SaaS companies aim for 120%+ NRR, meaning theyre growing revenue from their existing customers by at least 20% annually through upsells and expansions. And finally, they need to drive customer advocacy turning your best customers into references and case studies.

VPCs (Virtual Private Cloud) 156

VPCs (Virtual Private Cloud) Customer Success Churn Retention 156

SaaStr

FEBRUARY 1, 2025

How many times can you sell somewhat sorry but boring SaaS products? Its just hard to fly in sales selling something much harder to sell than your last role. But sell something even a smidge easier to sell than the last one? So long as its just a smidge easier to sell than the last one. Voice APIs? Call center analytics?

Sales Hiring 176

Sales Hiring Sales compliance Interviewing 176

SaaStr

NOVEMBER 8, 2021

Relative to any other sector, the SaaS industry is uniquely transparent. In my opinion, the most informative and useful SaaS content “speaks for itself” and is well suited for future reference. Bonus: More SaaS “Rule of 40” Data. Full Session YouTube. Full YouTube Session.

Scale 354

Scale Forecasting Cloud Pricing 354

SaaStr

MAY 24, 2022

Many mediocre hires were made to fill slots, reference checks not made, etc. If there really is a slowdown (and I’m not sure will be in SaaS), folks will have to work harder. So I’m not yet convinced times are really tougher for SaaS companies. Do reference checks, on and off sheet. So did startups. jasonlk) May 23, 2022.

Sales Hiring 315

Sales Hiring Sales Recruiting Interviewing Startup 315

Incredo

JANUARY 14, 2020

What just happened is that you entered another SaaS company’s sales funnel. And after a few days they will ask you to try their software for free. If you read our today’s post, you’ll know 1) how to setup your SaaS marketing funnel, 2) what stages to include, and 3) how to get the most out of it.

Sales Funnel 239

Sales Funnel SaaS Sales Social Media 239

SaaStr

DECEMBER 22, 2023

For any Cloud and SaaS Founders or execs seeking practical strategies and inspiration to stay ahead of the curve, this session’s for you. The six products/companies Kiren helped scale to $100M that he’ll reference in this playbook include: Bill, Cloudflare, Crowdstrike, Samsara, Snowflake, and Zscaler.

Scale 300

Scale Scaling Strategy Sales Hiring 300

SaaStr

JULY 22, 2021

Too many SaaS companies don’t really track what % of their customers come from word-of-mouth. To get that word-of-mouth/viral/refer ral engine going faster. The more you share success with your existing customers — the more they will refer more of their friends to you. More here. Make the sales team ask.

Sales Hiring 358

Sales Hiring Scale Customer Success Branding 358

TechEmpower SaaS

JULY 31, 2023

channels (search, social, viral, new media), cost-efficient distribution We often reference Dave’s work when talking to innovators. cto , infotech , innovation , product , project , saas Be sure to check out the entire presentation. Conclusion Startup metrics are an invaluable tool for founders and innovators.

Metrics 390

Metrics Startup Scale New CTO 390

SaaStr

MARCH 18, 2025

Laiva Becoming the platform of choice for life science companies and research institutions by creating a two-sided marketplace with significant SaaS components. SaaS vs. AI: A Misleading Analogy Unlike SaaS, AI isn’t necessarily disruptive to the existing tech stack.

Technical Review 179

Technical Review Artificial Intelligence AI Marketplace as a Service 179

SaaStr

MAY 1, 2025

For example, $1M ARR SaaS Startup Growing 15% MoMLooking for a Partner or Were the Next Rippling$500k ARR, 10x YoY Growth. Reference a tweet, blog post, or investment Ive made thats relevant to your pitch. Heres how to craft one that gets my attention (and likely others too): Start with an incredible subject line.

Scale 152

Scale Startup Investment Scaling 152

SaaStr

NOVEMBER 19, 2020

But, there are still many interesting things we can learn from Shopify, especially since it sells to so many SMBs, has been late to go upmarket, and combines a payments/fintech element with pure SaaS. As more and more SaaS apps add a payments element, that payments element can really scale over time. to promote your app?

Payments 363

Payments Merchant Services Payment Solutions Scale 363

SaaStr

MAY 27, 2025

5 Of The Best Ways to Retain Your Customers In SaaS in The Earlier Days … And After 2. These champions are the ones who will advocate for your product internally, drive expansion opportunities, and refer new customers. Most Churn Happens Early The first 90 days are where most churn happens. The 11 Year Customer 4.

Onboarding 176

Onboarding AI Customer Success Scale 176

SaaStr

JANUARY 8, 2022

Including those who have never sold SaaS before, or even, anything at all. Get 2-3 years of on-point SaaS experience, i.e. at a SaaS company that sells at your approximate price point. References Really Do Matter Here — from Customers Too if possible. Sometimes, references are just a Check the Box exercise.

Sales Recruiting 278

Sales Recruiting Sales Hiring Sales Pricing 278

SaaStr

JANUARY 5, 2024

Getting Outbound off the Ground in the Early Days Whatever stage your company is in, you can map wherever you are to outbound and use this article to either create, scale up or improve your outbound SaaS sales. So, how do you identify the right profile to recruit, given the limited real-world experience of an SDR?

Sales Hiring 305

Sales Hiring Sales Recruiting Scale Outbound Sales Team 305

SaaStr

APRIL 1, 2023

We stopped doing reference checks. While layoffs are all across the news today, looking back, July 2021 was the nadir for layoffs. Everyone was hiring everyone, anyone, back in mid-2021. This data from Carta helps illustrate it: So we cut corners. No time, didn’t want to know.

Sales Hiring 306

Sales Hiring Investment Leadership Startup 306

Clouded Judgement

JANUARY 24, 2025

In AI terminology, “generalizing” refers to a model’s ability to apply learned knowledge to new tasks or unseen data. The promise of SaaS is that growth in the early years leads to profits in the mature years. A core question is whether these powerful reasoning models truly “generalize” well.

Enterprise 157

Enterprise AI Cloud Artificial Intelligence 157

SaaStr

JANUARY 9, 2023

I see SaaS companies quickly get to cash-flow positive by really only servicing in-bound customers with high intent. Well at a practical level, many SaaS companies are doing a Strategic Sales & Marketing Retreat. This “flash diet” does work for many SaaS companies, at least the ones with mini-brands that are at scale.

Scale 327

Scale Sales Hiring Venture Capital Marketing 327

SaaStr

SEPTEMBER 24, 2023

Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: How to Do a Reference Check in 60 Seconds Building a Global SaaS Empire: 5 Bets That Paid Off with Freshworks How to Be a Much Better Sales Executive in About 60 Seconds Salesforce, Samsara, Monday and More: “Layoffs are Over.

Sales Hiring 278

Sales Hiring Scale Cloud AI 278

SaaStr

APRIL 29, 2021

The Covid Boost for SaaS. It would be so helpful to know, as the #1 leader in SMB eCommerce, and also one of the very top leaders in SaaS SMB overall. Most of Shopify’s revenue isn’t SaaS per se anymore, and it only includes actually software revenue in its MRR calculations. #4. 5 Interesting Learnings: #1.

Merchant Services 312

Merchant Services Payment Methods SaaS Payments Payments 312

Payrix

FEBRUARY 4, 2025

A master merchant, often referred to as a payment facilitator or merchant aggregator, is a third-party agent that acts as the link between acquirers and online merchants. The master merchantis the primary account holder for a payment processing system, overseeing and managing multiple subordinate accounts, often referred to as sub-merchants.

Merchant Services 130

Merchant Services Payment Services Payments SaaS Payments 130

TechEmpower SaaS

NOVEMBER 13, 2023

Maybe those references to TFA sound like bragging, or he thinks “passion for numbers” sounds silly. cto , infotech , innovation , product , project , saas The information provided was all pulled from data he’s already entered - just Mark, Houston, Math Teacher, Teach for America.

Generative AI 443

Generative AI Artificial Intelligence AI New CTO 443