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

OCTOBER 26, 2022

Grammarly CEO Brad Hoover shares the keys to unlocking product-led growth in the enterprise through learnings from the company’s 13+ year journey helping 50,000 teams and 30 million individuals refine their writing and accomplish their goals. The next focus point is how you enter the enterprise. . Forge your enterprise path.

Enterprise 252

Enterprise Scale Sales Communication 252

Casey Accidental

OCTOBER 20, 2020

This is part two of a three part series on sequencing business models. Casey’s first sequencing business models essay talked about the transition from a SaaS business model to marketplace business model, and why it’s so difficult. This essay is a collaboration with Gilad Horev.

Marketplace as a Service 141

Marketplace as a Service Business Model SaaS Payments Payments 141

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 147

Enterprise readiness Enterprise compliance Acquisition 147

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

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 300

SMB Payment Services Payments Payment Methods 300

SaaStr

MARCH 8, 2023

How did the largest product-led growth enterprise company in the world find success? But in general, urgency is always helpful, balanced with thoughtfulness for what you want your business to look like over the next 30 years. Determine whether you want to build a self-serve or sales business.

Sales Hiring 258

Sales Hiring Enterprise Headcount Scale 258

SaaStr

DECEMBER 21, 2022

If you run a successful, scalable business, the word “enterprise” will inevitably come up at some point—and for good reason. To survive, businesses need to evolve, and creating an enterprise offering for customers is part of the evolution of a business. What are the most successful markets for our business so far?

Scale 245

Scale Enterprise Scaling Management 245

SaaStr

DECEMBER 13, 2021

Linux is the #1 internet client, makes up 100% of the supercomputer market, and is second to Windows when it comes to enterprise software platforms. The developers you engage with often become your first adopters, who then become product evangelists—and they’ll help you scale and solidify trust within enterprises, too.

Enterprise 246

Enterprise AI SaaS AWS 246

Intercom, Inc.

OCTOBER 8, 2020

And the challenge is a lot harder in an enterprise context, where the buyer and the user aren’t necessarily one and the same person. Many businesses struggle to strike a balance between freemium’s light-touch customer engagement with the more involved enterprise sales process. Crowning the customer. Shortening the sales cycle.

Scale 205

Scale Sales Hiring Software Review Technical Review 205

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 161

Cloud AI Artificial Intelligence Healthcare 161

SaaStr

JULY 2, 2019

Join Kevin Egan, Slack’s VP of North American Sales and Dannie Herzberg, Slack’s Director of Sales as they walk you through Slack’s Freemium to Enterprise strategies. We’re here to talk for the next 25 minutes or so about our experience going from freemium to enterprise. Want to see more content like this?

Enterprise 164

Enterprise Scale Sales Hiring SMB 164

Incredo

MARCH 20, 2019

Software as a service, also known as SaaS, is a highly cost-effective software solution that offers a lot of agility for businesses. More companies are increasingly adopting SaaS solutions as they realize what a reliable option it can be for numerous business models and industries.

Trends 177

Trends Enterprise SaaS Business Model 177

SaaStr

OCTOBER 28, 2023

You’ll find as you get bigger, and deal sizes go up, fewer and fewer customers will do the work for a real free trial in enterprise deals at least. It’s harder to build an enterprise-grade product so intuitive, it can be used in seconds. Freemium is a business model. So it may matter less as time goes on.

Startup 294

Startup Payment Solutions Business Model Enterprise 294

Tom Tunguz

JUNE 10, 2024

Apple’s massive distribution will affect consumer & enterprise preferences. Enterprises push for their data to be under their control in virtual private clouds, in open data formats like Iceberg, to run AI models in their own environments - the cloud-prem architecture. It’s already happening.

AI Search 263

AI Search AI VPCs (Virtual Private Cloud) Sales 263

SaaStr

JUNE 19, 2024

Pricing AI Service-as-Software with Ununsual VC Sandhya Hegde, General Partner @ Unusual VC “Enterprise adoption of generative AI has hit an inflection point in 2024 with many successful tools productizing parts of professional services. Glean AI has rocketed to a $3B valuation by selling AI search to the enterprise. ” #4.

AI Search 293

AI Search Scale AI Generative AI 293

Tom Tunguz

JANUARY 22, 2023

Longer-term contracts & steadier enterprise buyers help smooth shocks for B2B companies. The main challenges facing B2B startups today are decreases in seat counts as their customers downsize & slower sales cycles which creates volatility in bookings , which has caused more layoffs than an anytime in the last four years.

B2C 315

B2C B2B Headcount Business Model 315

SaaStr

AUGUST 10, 2022

This is the secret sauce to Atlassian’s business model. So while Atlassian has plenty of enterprise customers, it hasn’t gone that enterprise. And come join Atlassian’s CRO LIVE at 2022 SaaStr Annual on Sep 13-15 sharing how they scale their unique business model!

Scale 277

Scale Headcount Cloud Forecasting 277

SaaStr

SEPTEMBER 9, 2022

Traditional software had 90% gross margins, and the classic enterprise sales reps, the best ones, could close a million or more dollars a year. Not a bad thing per se, but it also put a lot of pressure on business models. Sales reps in low NRR and high churn environments got paid almost the same as enterprise reps.

Scale 343

Scale Venture Capital Sales Hiring Sales 343

SaaStr

JUNE 1, 2021

You’ll find as you get bigger, and deal sizes go up, fewer and fewer customers will do the work for a real free trial in enterprise deals at least. It’s harder to build an enterprise-grade product so intuitive that it can be used in seconds. Freemium is a business model. One side benefit you get is a better product.

Scale 332

Scale Engineering Enterprise Business Model 332

Andreessen Horowitz

MARCH 21, 2024

In 2024, we believe the revenue opportunity will be multiples larger in the enterprise. Some naysayers doubted that genAI could scale into the enterprise at all. As always, building and selling any product for the enterprise requires a deep understanding of customers’ budgets, concerns, and roadmaps. Isn’t this all hype?

Generative AI 145

Generative AI Enterprise AI Artificial Intelligence 145

SaaStr

FEBRUARY 27, 2023

They credit this growth to their global team, a switch to an enterprise business model switch, and flexible work operations. Moving from self-service to enterprise As your product improves, your user demands change, requiring a revamp of the business model to satisfy high-paying customers.

Scale 245

Scale Sales Hiring Sales Recruiting Scaling 245

SaaStr

OCTOBER 11, 2023

▶️ Radically more efficient, $600m+ adj operating income run-rate ▶️ 29% of biz from enterprise (Plus) — Jason ✨Be Kind✨ Lemkin  (@jasonlk) October 10, 2023 5 Interesting Learnings: #1. From a business model perspective, Shopify has in essence been a fintech and merchant product first and a SaaS product second for quite some time.

Payments 286

Payments Merchant Services Revenue Payment Solutions 286

SaaStr

AUGUST 26, 2024

Plus, three of the closing sessions will be open to the broader audience of Annual this year: Customer Success in Different Business Models with Slack, Mulesoft, and OpenAI : In this session , these three CS leaders will discuss how customer success strategies differ across various business models.

Benchmarks 286

Benchmarks Finance Business Model Forecasting 286

SaaStr

OCTOBER 25, 2021

“[You] have to get some sort of dollar commitment for pilots in Mid Market and Enterprise deals. ” and “Something we found really effective at CoursKey, and other vSaaS businesses will likely find as well: Instead of running pilots, sign a multi-year contract but give them an opt-out after 3-6 months. .

Pricing 317

Pricing Scale Enterprise Onboarding 317

SaaStr

DECEMBER 31, 2019

With the complexity of multiple stakeholders and the increasing purchasing influence of end users, the bar is higher than ever for enterprise UX as companies pioneer business models beyond traditional SaaS. Very excited to talk to you today about building consumer grade products for the enterprise. Shanee Ben-Zur.

Enterprise 162

Enterprise Underperforming Technical Team Scale B2B 162

SaaStr

OCTOBER 31, 2023

With nine figures in revenue, Ariel and SaaStr founder and CEO Jason Lemkin talk about all things Navan, rebranding when you have brand equity, building B2B software for people, pricing and business models, and much more. It’s possible and even wonderful to create products for Enterprise and B2B that users love to use.

Payment Solutions 276

Payment Solutions Payments Travel Scale 276

SaaStr

JUNE 22, 2023

SaaStr Trying to pursue a “Grass is Greener” business model. Enterprise folks want to do freemium because they think it is easier. Perhaps most importantly these days, “PLG” does not magically make a business model work, or a product magically sell itself. But they can challenge how you think about the market.

SMB 269

SMB SaaS B2C Interviewing 269

SaaStr

FEBRUARY 27, 2021

Together, they are one of the most critical topics in recurring revenue business models. Because in the enterprise, customers aren’t just buying bits. There’s a lot to talk about in customer success about churn, and about upsells. So should you? Or should you keep doing everything over Zoom? For your top customers.

Business Model 345

Business Model Customer Success Churn Software 345

SaaStr

JANUARY 12, 2022

“For large enterprise customers, your stakeholder map is almost always too small” — Alex Farmer, VP CS, Cognite Data. Another top mistake SMB folks make trying to sell enterprise. You lose enterprise deals when someone that knows the playbook outsells you by getting to all the stakeholders. A good one.

CTO Hire 321

CTO Hire Sales Hiring New CTO CTO 321

SaaStr

NOVEMBER 25, 2022

They demonstrate spectacular growth and expansion while revolutionizing and disrupting industries with new business models. Scaling to satisfy customers’ demands depends on innovation and foresight combined with enterprise-ready technology and the right partners. How Atlassian does business . Scale-ups are exciting.

Scale 258

Scale Scaling Marketplace as a Service Entrepreneurship 258

SaaStr

FEBRUARY 14, 2021

One con is that these businesses often are tougher to gain a longer-term competitive advantage in unless there is a network effect (e.g., But from a business model perspective, why invest in sales, demand gen, and all that if you don’t have to? Even if it’s just for an Enterprise of Five.

Revenue 258

Revenue Sales Hiring Customer Lifetime Value Churn 258

SaaStr

DECEMBER 29, 2021

An open core business model empowers customers and fosters brand loyalty. At GitLab, we run on an open core business model. We have a dollar-based gross retention rate of 97% and it’s in part because of our open core model. Clearly and publicly state your business practices.

Innovation 246

Innovation Business Model Banking Scale 246

SaaStr

JULY 5, 2023

And here you can see the magic in Mongo’s business model. Top 100 Customers are 33% of Revenue, and Enterprise Customers are 75% of Revenue. 75% of their revenue is Enterprise, even though it’s a small percent of total customer count. Wow, just an epic product, CEO, business model, and success story.

Scale 242

Scale cloud efficiency Cloud Business Model 242

Andreessen Horowitz

OCTOBER 12, 2023

What do enterprise buyers in healthcare care about most when evaluating AI products? We’ve designed this to mirror the thought process of an entrepreneur building an AI product with an enterprise use case. Across our conversations, enterprise buyers emphasized repeatedly that their procurement decisions start with the problem in mind.

Healthcare 114

Healthcare Payments AI Enterprise 114

SaaStr

MAY 19, 2022

You can use product-led growth even in an enterprise model. For example, every employee of a 1Password customer gets a free family account with the enterprise model. Many companies are too focused on growing in size without first understanding if they have a viable business model. Profitability is power.

Development Team Review 286

Development Team Review B2C Compensation Technical Review 286

SaaStr

JUNE 12, 2020

Both sell to the Enterprise. Before you try to copy Zoom’s business model, you really need to understand it. There are some questions in SaaS that are, at some level, almost a mystery: Why was Veeva able to burn only ~$10m net on its way to an IPO? Yet Box needed $250m? So it’s not that. That helps a ton.

Scale 337

Scale SaaS Business Model Strategy 337