SaaStr

MAY 28, 2025

It never had a downturn, and just keeps on growing at top-tier rates, selling both to SMBs and now larger enterprises. Monday.com’s Upmarket Strategy is Working Well Monday.com is clearly executing an effective enterprise push. The company is successfully evolving from its SMB roots into a serious enterprise software contender.

Scale 194

Scale SMB Acquisition Enterprise 194

SaaStr

JULY 11, 2025

This consumer base provides: Brand recognition : ChatGPT has become synonymous with AI for many users Data flywheel : Millions of interactions improve model training Market validation : Consumer enthusiasm drives enterprise interest Revenue diversification : Both subscription and API revenue streams Anthropic’s Enterprise-First Approach Anthropic (..)

ChatGPT 223

ChatGPT Artificial Intelligence Outsourced Development AI 223

SaaStr

FEBRUARY 26, 2025

The $10M ARR Rule for Enterprise Here’s a controversial but important take: If you’re under $10M ARR, stay away from Enterprise. Because too many startups fall into what Gross calls the “Enterprise Mirage” – landing a few big logos through heroic efforts but failing to build repeatable systems.

Enterprise readiness 144

Enterprise readiness Enterprise compliance Acquisition 144

SaaStr

FEBRUARY 2, 2025

Companies need to: Ensure secure data handling Maintain clean data for model training Integrate effectively across multiple systems Enable real-time data access where needed Evolution of Business Models The integration of AI is driving changes in how vertical software companies approach pricing and business models: Pricing Strategies Traditional subscription-based (..)

AI 217

AI Technical Review Artificial Intelligence Systems Review 217

SaaStr

OCTOBER 23, 2024

Selling to Multiple Stakeholders If you sell into the Enterprise, you understand there are different stakeholders. With SMBs, the smallest business is owner-operated. A mobile phone is their dominant source of managing business activities. When you’re “cheap,” you’re more immune to some of these effects. This is true for BILL.

SMB 307

SMB Payment Services Payments Payment Methods 307

SaaStr

JUNE 28, 2025

This pipeline represents over $200 billion in combined enterprise value, with companies spanning critical infrastructure, productivity tools, security, and financial services. The diversity demonstrates the breadth of enterprise software innovation ready for public markets. HubSpot, Box, Shopify).

Payments 182

Payments SaaS Payments Payment Services AI 182

SaaStr

JUNE 9, 2025

from IPO price Key Learning : Enterprise financial software with strong integration capabilities can command solid premiums in the CFO-focused market The 5 Critical Metrics Every B2B Leader Should Track for IPO Readiness Based on analyzing these successful (and not-so-successful) public companies, here are the metrics that matter most: 1.

B2B 184

B2B Marketing Scale Benchmarks 184

SaaStr

FEBRUARY 10, 2025

25x’d Revenue and Crossed $100M ARR Apollo.io, an all-in-one go-to-market platform, underwent a significant transformation in its business model that led to remarkable growth. This aligned with their new focus on serving small and medium-sized businesses more effectively. From Sales-Led to Product-Led: How Apollo.io

Scale 159

Scale Scaling Outsourced Development Sales 159

SaaStr

MARCH 18, 2025

The harsh reality: Most enterprises are adopting AI due to FOMO (Fear Of Missing Out) rather than for specific business outcomes. Project Selection: Where Enterprises Go Wrong Many companies stumble by deploying AI in high-risk, customer-facing applications first (like chatbots). This is exactly backward.

Technical Review 184

Technical Review Artificial Intelligence AI Marketplace as a Service 184

SaaStr

MAY 2, 2025

“The Last Generation of Human-Only CEOs: Marc Benioff’s Bold Vision for the AI-Augmented Enterprise” Marc Benioff was kind enough to join SaaStr for the first time to do a truly deep dive on what AI means in business software today. It’s a good one. Top 5 Unexpected Learnings: 1.

AI 243

AI Enterprise Scale Airlines 243

SaaStr

OCTOBER 11, 2024

But when we got started in Cloud in 2007, most businesses that were starting with cloud picked one cloud. Multi-cloud really didn’t arrive for many years in a high penetration rate of how enterprises were building their applications. When working with AI apps and models, the outcomes are more probabilistic.

Cloud 167

Cloud AI Artificial Intelligence Healthcare 167

Clouded Judgement

JUNE 6, 2025

This “misuse of ARR” trend has accelerated in the age of AI, as business models have evolved (into more usage/success-based vs. seat-based), and everyone is tinkering with new AI products. Multiples shown below are calculated by taking the Enterprise Value (market cap + debt - cash) / NTM revenue. ” Pilots.

Cloud 144

Cloud Technical Review Software Review Technical Advisors 144

Stax

JUNE 18, 2025

Activant Capital reports : Vertical SaaS is outpacing traditional enterprise software growth by a significant margin. While enterprise software grew at 11.1% According to Fractal Software , “Vertical SaaS businesses don’t set out to fundamentally change the industries they operate in by replacing key parts of their workflows.

Merchant Services 167

Merchant Services SaaS Payments Payment Services Payments 167

Sales Enablement, SaaS and Growth

JUNE 9, 2025

The Brief To help sales leaders navigate the complex world of frameworks and selling styles, I created an AI-powered Sales Methodology Selector - a sleek, interactive tool that recommends the best approach based on business model, industry, deal size, and sales cycle.

ChatGPT 130

ChatGPT Artificial Intelligence Sales Strategy 130

SaaStr

JUNE 23, 2025

The CEO who delegated AI strategy to someone who “really gets AI” discovered too late that AI strategy is business strategy. The companies winning with AI aren’t optimizing existing processes—they’re creating entirely new business models. It’s the date where the excuses run out.

AI Search 172

AI Search AI Technical Review CTO Hire 172

User Pilot

OCTOBER 19, 2024

It’s designed for B2B enterprises that require advanced capabilities to collect and analyze customer feedback from B2B markets, and from multiple channels. Why it’s worth considering : Qualtrics is perfect for omnichannel B2B enterprises looking for measuring user sentiment in B2B markets. Multi-language support.

Software Review 105

Software Review Technical Review Software B2C 105

Blulogix

JUNE 13, 2025

By BluLogix Team What Enterprises Really Need from Agile Billing—And Why Most Platforms Can’t Deliver, According to MGI Research For years, the billing software market has been flooded with tools that promise flexibility, automation, and ease of use. Most of them were built for startups, SMBs, or simple direct-to-consumer models.

Payment Features 59

Payment Features Enterprise Traceability Scale 59

Valuize Consulting

FEBRUARY 8, 2025

Establishing criteria for ideal partners, including business models, expertise, and competencies, is critical to long-term success. NPS, CSAT) Regular governance meetings, quarterly business reviews (QBRs) with partners, and management-level reporting will ensure continuous improvement of your partner-led customer success model.

Customer Success 52

Customer Success Scale Technical Review Government 52

Chart Mogul

DECEMBER 12, 2024

Code generators will be less deflationary than open source, and recurring revenue pricing will continue to be the greatest business model in the history of capitalism. Traditionally it’s been seen as complex and costly, suitable only for large enterprise motions. AI will complement, not replace traditional SaaS platforms.

Fractional VPE 40

Fractional VPE Software Review SaaS Part-Time VPE 40

SaaStr

JULY 1, 2025

Companies are “increasingly adopting a multi-model approach, leveraging different providers based on use case, performance, cost, and customer requirements.” ” Why This Matters : No single model wins across all dimensions. The Tactical Insight : Build model-agnostic architectures from day one.

AI 198

AI Software Review Technical Review Scale 198

SaaStr

JUNE 1, 2025

The latest one is all AI with a big enterprise / B2B slant and is very good but dense. The Monetization Models Are Still Completely Broken The Venture-Scale Burn: OpenAI (estimated): 2024 Revenue: ~$3.7B Competition from open-source models and Chinese providers could make it impossible to maintain premium pricing. 300+ pages.

AI Search 259

AI Search AI CTO Hire ChatGPT 259

SaaStr

JULY 11, 2025

margin) Enterprise Heavy (20% light, 40% typical, 30% heavy, 10% power users): Revenue: $20,000 Costs: $24,288 Profit: -$4,288 (-21.4% Companies subsidize the heaviest users to drive adoption and land enterprise deals, hoping to figure out the economics later. Enterprise customers are already demanding this balance.

Pricing 211

Pricing Venture Capital Scale AI 211

SaaStr

JULY 8, 2025

But Won’t Be Profitable Until $125 Billion in Revenue The staggering numbers behind OpenAI’s growth trajectory sparked intense discussion about AI business models and the path to profitability. Great dashboards remain the primary way enterprise customers perceive and demonstrate value from their SaaS investments.

Scale 172

Scale AI Sales Business Model 172

Sales Hacker

JANUARY 7, 2025

Yeah, it could be a center at the enterprise, or it could be, as you said, the small fractional CRO that happens to work with everyone in a fintech vertical, if you sell into fintech, or you got to, you know, map those out. And what does it mean for business model? Scott Barker: Yeah, totally.

Outsourcing Services 117

Outsourcing Services Scale Outsourced Development AWS 117

SaaStr

JUNE 26, 2025

The SaaS Lesson : When your core business model faces platform risk, the cost of defensive innovation isn’t measured against ROI—it’s measured against the cost of irrelevance. MCP and The Fight Over Whose Data it is: The Coming Enterprise Software Revolt Cluely: The Future of Sales or Just Crazy Marketing?

Artificial Intelligence 243

Artificial Intelligence AI ChatGPT B2B 243

Blulogix

JUNE 18, 2025

Invoices can be white-labeled, branded with the partner’s name, and configured to handle taxes, revenue share, and collections—all based on your business model. It’s a signal that the market is shifting—from generic invoicing tools to platforms that align with strategic growth models.

Payment Features 52

Payment Features Underperforming Technical Team Outsourced Development Systems Review 52

Stax

MARCH 18, 2025

Additionally, ensure the processor works well with other business tools like CRM, enterprise resource planning (ERP), and accounting software. The ideal pricing structure for your business depends on various factors, such as your business model, your customers preferred payment methods, and monthly/annual transaction volumes.

Payment Services 88

Payment Services Merchant Services Payment Methods Payment Solutions 88

Sales Hacker

MAY 13, 2025

He also co-founded WGI Group, LLC, to provide growth capital to early and expansion stage startups in enterprise software, consumer internet and digital media industries. LLC to provide growth capital to early and expansion stage startups and enterprise software, consumer internet and digital media industries. Amazing, awesome.

AI Search 74

AI Search AI ChatGPT Software Review 74

SaaStr

JULY 10, 2025

The long tail in commerce is often bigger than the “enterprise” segment. The Core Strategic Divergence The fundamental difference between Olo and Toast isn’t just about technology – it’s about market segmentation philosophy that has created two entirely different business models with dramatically different outcomes.

Technical Review 172

Technical Review Payments Scale Payment Solutions 172

SaaStr

MAY 27, 2025

While consumer apps chase viral growth, enterprise infrastructure compounds quietly. While consumer apps chase viral growth, enterprise infrastructure compounds quietly. The Second IPO Strategy Is Real Sometimes you need to go private to reinvent your business model. Let’s break down the lessons.

Acquisition 144

Acquisition Government AI Enterprise readiness 144

Stax

FEBRUARY 19, 2025

Gartner predicts that, through 2022, 60% of organizations will prioritize transitioning to a composable enterprise model. Q: How do APIs contribute to the success and sustainability of business models? APIs contribute to the success and sustainability of business models by enhancing their flexibility and interoperability.

Payments 88

Payments Merchant Services Payment Services Payment Solutions 88

Sales Hacker

JUNE 20, 2025

Business models or motions you excel in (e.g. PLG, enterprise SaaS, marketplaces). Instead, write a Focus Statement – a short, specific summary that makes it incredibly easy for someone to help you. What to include: Role(s) you’re targeting. Stage and segment you’re best suited for. Words of advice from a Chief Customer Officer.

Sales Hiring 102

Sales Hiring Sales Recruiting AI Search Scale 102

SaaStr

FEBRUARY 9, 2025

Most importantly, they’ve proven that word-of-mouth growth driven by product excellence can build a more sustainable business than traditional enterprise sales approaches. It’s a playbook worth studying for any SaaS company looking to dominate their vertical.

Sales Hiring 239

Sales Hiring Marketing Scale B2C 239

User Pilot

FEBRUARY 24, 2025

Those with experience in enterprise-level AI platforms. Candidates short profile Spencer has over 7 years of experience driving product vision , strategy, and execution in AI-powered and enterprise SaaS platforms. She will optimize business models for profitability and operational efficiency. Android-first PMs.

Technical Advisors 52

Technical Advisors Data Management Scale 52

SaaStr

FEBRUARY 18, 2021

Box has grown to almost $1B in revenue , but it “tilted” from a mostly freemium product to an enterprise focus, with freemium today being about 9% of their revenue — although a key source of leads (see below). Slack added a big enterprise sales team. Zoom always had a sales team, and is going more enterprise.

Business Model 293

Business Model Scale Business PayPal 293

SaaStr

MAY 1, 2021

How does a SaaS company reach enterprise buyers? Enterprise decision-makers have unique problems they need to solve, but they don’t always have time to experiment with a platform or sit through dozens of software demos to find the right solution. A Different Way to Approach Enterprise Leads .

Enterprise 314

Enterprise Scale B2C SaaS 314

Intercom, Inc.

OCTOBER 16, 2019

The SaaS industry is constantly evolving, and for many companies in the space, that means having to evolve their business model. However, that doesn’t necessarily mean a “pivot”, but more often the evolution is a shifting business model as the company scales and the user base grows and changes. Gaining new customers.

Business Model 195

Business Model Scale Pricing Payment Methods 195