Clouded Judgement

MARCH 28, 2025

Data from Stripe (below) shows the speed at which AI native companies are growing compared to SaaS companies. Now let’s talk about the AI wave. And now there’s another exponential drop off in complexity to start a company going from the cloud world to the AI native world. In the AI world, you’re never too late.

Cloud 184

Cloud AI Scale Scaling 184

SaaStr

MARCH 18, 2025

Joselyn Goldfein , Managing Director at Zeta Venture Partners, which invests in AI and data infrastructure-focused startups from inception through seed stage And see everyone at 2025 SaaStr Annual, May 13-15 in SF Bay!! What VCs Are Funding in AI Today The AI funding landscape has evolved rapidly in 2023-2024.

Technical Review 191

Technical Review Artificial Intelligence AI Marketplace as a Service 191

Clouded Judgement

JANUARY 24, 2025

Subscribe now The Year of “Enterprise AI” One of the biggest challenges facing AI systems in enterprises today is the “last mile” problem: how do you make AI both reliable and accurate for specific enterprise use cases? This is what I’m calling “Enterprise AI.”

Enterprise 157

Enterprise AI Cloud Artificial Intelligence 157

Tom Tunguz

FEBRUARY 26, 2025

” The company grew from $15M in ARR to more than $1B with this model, consistently achieving better than 130% net dollar retention. With this model, Twilio maintained contracted revenue at less than 50% of ARR while achieving industry-leading retention metrics. The ratio of AI price to base price ranges from 0.32

SaaS Payments 283

SaaS Payments Pricing Strategy Scale 283

SaaStr

OCTOBER 23, 2024

At SaaStr’s AI Summit during the SaaStr Annual , René chatted with SaaStr CEO and founder Jason Lemkin about how BILL has reached half a million customers and $1.3B At BILL, logo retention is 86% in the first 90 days. AI Learnings “Fundamental technologies become fundamental, not because of hype,” René says. in revenue.

SMB 310

SMB Payment Services Payments Payment Methods 310

Tom Tunguz

MAY 16, 2024

Ramp published its quarterly spending trends & revealed how businesses are spending on AI. There are many great data points that underscore the growth in AI but there are important nuances in the patterns. First, AI growth rates across the most popular vendors have fallen 78% annually.

AI 300

AI Churn Trends Pricing 300

SaaStr

APRIL 15, 2025

Series A Success Strategies for 2025 Ethan shared several critical strategies for founders approaching Series A: Understand your “why” : Clearly articulate why you’re raising capital and what you’ll do with it beyond simply “it’s time for the next round.”

Technical Review 159

Technical Review Venture Capital Outsourced Development AI 159

Clouded Judgement

FEBRUARY 7, 2025

Subscribe now “Grouping + AI” for Triage One area I’m quite excited to see AI revolutionize is “grouping + triage” workflows. Many of them AI based. Every week I’ll provide updates on the latest trends in cloud software companies. Follow along to stay up to date! Perfect for a LLM!

Systems Review 144

Systems Review Cloud AI Artificial Intelligence 144

SaaStr

MARCH 1, 2024

Generative AI is a platform shift where models can take inputs such as text, image, audio, video, and code and generate new content into any of the modalities mentioned. The Pace of AI is Increasing Dramatically Something ground-shifting has been happening over the last five years — the pace of innovation.

Generative AI 296

Generative AI Outsourcing Services AI Software Review 296

SaaStr

AUGUST 12, 2024

The post New SaaStr Annual Speakers Alert: CROs of Rippling, Checkr and DeepL; CBO of Stripe; Bessemer’s State of the Cloud: AI Edition appeared first on SaaStr. And so, so much more!! See everyone in SF Bay, Sep 10-12 at SaaStr Annual 2024 !

Cloud 293

Cloud AI Scale Customer Success 293

SaaStr

JANUARY 3, 2025

If you missed part 1 of this interview, you can catch up on their conversation about the current state of SaaS, evolving board meeting formats, and how AI is reshaping the industry. HubSpot recently changed its interview process to try and help maximize tenure and employee retention at the executive level.

Sales Hiring 287

Sales Hiring Scale Systems Review Interviewing 287

Tom Tunguz

JULY 11, 2024

In a world where AI agents are 2.5-3x Building on yesterday’s post , pricing in software companies may change significantly when AI agents become the norm. There a few alternatives : Triple the per seat price : If the AI agent is 3x as productive as a human, the software company could charge 3x as much per seat.

AI 240

AI Pricing Software Compensation 240

SaaStr

MARCH 24, 2025

Some fun facts: 10+ years of SaaStr conference attendance Partner at Point Nine Capital, a leading early-stage VC firm Geographic reach: Actively investing across Europe, US, and Australia Notable portfolio: Zendesk, Algolia, Contentful, Loom (and many more) Known for his “five ways to build a $100M business” framework The 5 Key Things (..)

Data 147

Data Acquisition AI Finance 147

Andreessen Horowitz

MAY 7, 2024

For consumer products, the rubber hits the road at retention. Great retention is a natural result of delivering the core product value to users, which of course varies by product. Can these “retention boosters” apply to them? Here are the 7 most effective ways for AI-native consumer companies to improve their retention.

AI Search 104

AI Search AI Retention Artificial Intelligence 104

Clouded Judgement

MARCH 22, 2024

Enterprise software businesses strive for 90-95% gross retention (generally the percent of revenue that sticks with you vs churns altogether), with net expansion in the 120%+ range (the aggregate change in expansion - contraction - churned revenue). Namely, retention!! For “fake” ARR, retention can vary wildly.

AI 190

AI Cloud Revenue Technical Advisors 190

Tom Tunguz

SEPTEMBER 10, 2024

Account executive to SDR ratios, sales cycle lengths, conversion rates, customer acquisition costs, customer lifetime values, net dollar retention. These were my take aways : Selling AI is being discovered because the technology is new. Fight the empty box problem with great concrete templates that demonstrate how to use AI.

Software 304

Software Sales Hiring Customer Lifetime Value Scale 304

Tom Tunguz

JUNE 12, 2024

Quarter Q2 2023 Q2 2024 Quarterly Revenue, $m 375 600 Revenue Growth 50% 60% Customers 10,000 Gross Margin 85% 80% Net Dollar Retention 140% Data Warehouse Revenue, $m 200 400 Average Annual Customer Value 37,500 Net dollar retention is a major driver of growth at 140%, which is top decile.

AI 288

AI Retention Revenue Data 288

Blulogix

MARCH 27, 2025

By BluLogix Team How AI is Transforming Billing Billing has long been a complex and manual process, prone to errors, inefficiencies, and revenue leakage. AI is addressing these inefficiencies, transforming billing into a data-driven, automated, and predictive process.

Payments 59

Payments AI Search Payment Services AI 59

ChurnZero

NOVEMBER 8, 2024

Enter generative AI: a game-changer for customer success. Today, generative AI presents an unprecedented opportunity to tackle these challenges. It empowers businesses to deliver real-time, data-driven personalization while automating key tasks—ultimately driving retention and growth. AI enables action-oriented support.

Generative AI 52

Generative AI Scale AI Customer Success 52

SaaStr

MAY 30, 2024

It’s an end-user-focused growth model where your product drives acquisition, activation, expansion, and retention. AI can create churn drivers, and that data can be useful for customer success or for sales teams to have proactive conversations with customers. Leverage AI to assist sales. That’s PLG. Why is it end user-focused?

Scale 302

Scale AI Search Azure Sales 302

SaaStr

JANUARY 12, 2024

SaaStr CEO Jason Lemkin also wrote how Customer Success has now morphed into part of the sales team and that the 2024 trends in CS include everyone wanting to eliminate humans from support to replace that headcount with AI and bots. We still want to drive retention and growth and make money. The world has changed. Never stop,” he said.

Sales Hiring 321

Sales Hiring Customer Success Scale AI 321

Blulogix

MARCH 24, 2025

By BluLogix Team AI Billing Innovations, Usage-Based Pricing, Credits, and Prepaid Models AI Billing Needs a New Approach Unlike traditional SaaS, AI products often require real-time metering and consumption-based pricing. Example: Many AI platforms offer a free tier with limited credits, encouraging upgrades when usage grows.

AI Search 59

AI Search Payments Innovation AI 59

SaaStr

JULY 17, 2024

But those kinds of deals are back and only in the segment of AI. Yesterday, they published that GRR fell into the 80s, so revenue retention and cash flow weren’t there. It seems like the only way to do this is in AI. Does AI partially fuel this? These crazy 100x ARR deals in AI are expecting OpenAI-like growth.

Venture Capital 307

Venture Capital AI Cloud Scale 307

Clouded Judgement

JULY 12, 2024

Subscribe now The Red Queen Effect I strongly believe in two competing truths with respect to AI and its impact - the size of the prize will be bigger than we imagine now, BUT we’ll overestimate it in the short term. Right now the world is evolving - AI is a massive platform shift. And I think (for now) the latter is much larger.

Cloud 288

Cloud AI Investment User Experience 288

SaaStr

FEBRUARY 14, 2024

It’s the critical piece for customer retention. And that’s where AI comes in. If You Haven’t Embraced AI, You’re Falling Behind Organizations are being asked to become more efficient and to do that, they’re looking to AI. 43% of CS teams have adopted AI, which means that 57% have not.

Customer Success 302

Customer Success Sales Hiring Scale Headcount 302

Clouded Judgement

JUNE 19, 2024

net retention and CAC payback). Net Revenue Retention High net revenue retention is the fourth aspect of a successful quarter, and one of my favorite metrics to evaluate in private SaaS companies. Here’s the data from Q1: We have seen net dollar retention start to trail off in the last couple quarters.

Cloud 318

Cloud GCP(Google Cloud Platform) Software Azure 318

Tom Tunguz

NOVEMBER 12, 2023

Recently, I was on the HR Heretics podcast and we talked about the increasing efficiency of software companies (in addition to other topics including the implications of AI for executives, how to diligence a candidate, & what board members expect of their people leaders). Perhaps another doubling ( driven by AI! )

Software Review 331

Software Review Trends Revenue Software 331

User Pilot

OCTOBER 19, 2024

Personalize surveys by setting conditions based on user behaviors , translating and localizing your NPS surveys using AI, and customizing the appearance of your surveys to match your app’s design. Leverage AI-driven sentiment analysis to analyze and categorize open-ended responses quickly.

Software Review 105

Software Review Technical Review Software B2C 105

User Pilot

NOVEMBER 7, 2024

Collect customer data to calculate complex formulas for tracking metrics, monitor customer health scores, and resolve support tickets while continuously trying to improve retention and expansion. SmartKarrot Best for : Handling customer growth and account management (expansion and retention) operations. G2 rating : 4.8 G2 rating : 4.4

Customer Success 105

Customer Success Enterprise Software Review Startup 105

SaaStr

JANUARY 31, 2021

“The Current State of SaaS Companies, Subscriptions and Retention with ProfitWell” A great update from a version of this data just after Covid hit. #3. Learn how they build a high-retention culture. #10.

Scale 263

Scale Technical Review AI Sales Enablement 263

Andreessen Horowitz

MAY 17, 2024

In this episode of the AI + a16z podcast, a16z partners Guido Appenzeller and Matt Bornstein discuss the state of the generative AI market, about 18 months after it really kicked into high gear with the release of ChatGPT — everything from the emergence of powerful open source LLMs to the excitement around AI-generated music.

Generative AI 125

Generative AI AI Artificial Intelligence ChatGPT 125

Blulogix

MARCH 17, 2025

By BluLogix Team Why Consumption-Based Pricing Drives Higher Customer Retention Introduction One of the biggest challenges in subscription-based businesses is churn. Consumption-based pricing solves this by ensuring customers pay only for what they use, improving satisfaction and retention.

Retention 59

Retention Pricing AI Search B2B 59

SaaStr

JANUARY 29, 2021

Gross revenue retention just as important as net revenue retention (NRR). As Saleloft starts to think about an IPO, there is more and more focus on gross revenue retention, i.e. before upsells and upgrades. Instead, he argues that AI should enhance the human-to-human sales experience.

Scale 304

Scale Social Media SMB AI 304

USIO

MARCH 7, 2025

Integrated payment solutions incorporate advanced security measures such as tokenization, real-time fraud detection, and AI-powered analytics to reduce these risks. How Integrated Payments Drive Revenue Growth Enhancing Customer Experience A seamless, frictionless payment process improves customer satisfaction and retention.

Payments 130

Payments SaaS Payments Payment Solutions Payment Services 130

Clouded Judgement

JUNE 30, 2023

Subscribe now Data + Compute = AI Two of the largest data companies in the world, Snowflake and Databricks, held their annual conferences this week. To truly take advantage of AI, enterprises need organized data in the cloud. The challenge is probabilistic answers don’t work for true enterprise specific AI.

AI Search 130

AI Search AI Cloud Data 130

Andreessen Horowitz

SEPTEMBER 13, 2023

It’s been 9 months since ChatGPT was released and 7 months since it became the fastest consumer application to reach 100 million monthly active users , ushering in a new era of generative AI. But other than ChatGPT, how are consumers interacting with generative AI (GenAI) products? Who might be the next “big winner”?

Generative AI 145

Generative AI AI ChatGPT Artificial Intelligence 145

Andreessen Horowitz

SEPTEMBER 18, 2023

In enterprise healthcare, there are many “Jobs to be Done” (JTBD) for AI. To this end, we present the first part of the 6th episode of the Digital Health Go-to-Market Playbook series –Commercializing AI in Healthcare. Enterprise healthcare tasks are highly complex and unforgiving to errors.

Healthcare 140

Healthcare AI Artificial Intelligence Payment Solutions 140