SaaStr

FEBRUARY 7, 2025

With Databricks now one of the largest pre-IPO technology companies, with $10 billion of expected non-dilutive financing and a valuation of $62 billion, Ron’s insights are gold for any revenue leader looking to scale. His view is your sales team teaches your customers how to get value out of your product.

Scale

SaaStr

JULY 11, 2025

The Enterprise-Grade Platform That Makes AI Voice Agents Actually Work at Scale We’re proud to announce that Syllable is returning as a partner for SaaStr Annual + AI Summit 2026 , following their tremendous success and impact at our 2025 event. Your AI agents qualify leads 24/7 while human experts focus on complex cases.

Payment Solutions

SaaStr

MAY 26, 2025

So what does that mean for inside sales? A 50/50 Sales Team. At least for SMB and more routine mid-market sales. By 2026, these same AI systems will have evolved to manage entire sections of the sales process autonomously. An A+ AI will soon join every sales call, for real. Probably something similar by 2026.

Scale

SaaStr

JULY 1, 2025

Insights from Jasper Carmichael-Jack, CEO of Artisan at 2025 SaaStr AI Summit About Artisan: AI-powered sales platform building the end-to-end solution —from marketing personalization to AE automation across the entire revenue cycle. Sales is messier. CRM data accuracy sits at 47% across most sales orgs.

Scale

SaaStr

MARCH 18, 2025

It’s an incredible look back on scaling and more: Colin Jones, first Chief Revenue Officer at Wiz. The result was a 5x increase over initial projections – growing from an $8M revenue target to $40M actual results – driven by a belief that market demand justified the investment.

Scale

SaaStr

JUNE 19, 2025

✨ Lemkin (@jasonlk) June 16, 2025 The Top 3 Reasons AI Sales Tools “Don’t Work” (Spoiler: They Actually Do, If You Use The Tools Properly) I get this question at least 3x a week: “Jason, we tried AI sales tools and they just don’t work. I’ve been in B2B and Saa sales for 15+ years.

Scale

SaaStr

NOVEMBER 13, 2024

Klaviyo dominates marketing in the Shopify ecosystem and in ecommerce, and just keeps on scaling. But it’s clear that it’s still in the investing phase, and increasing spend in sales & marketing. So the latest SaaS leader to cross $1B ARR is Klaviyo. It was the only SaaS IPO on 2023. The only one!

Scale

SaaStr

JULY 23, 2025

Managing revenue operations (RevOps) in a SaaS company is all about aligning sales, marketing, and customer success to drive growth efficiently. Align Sales, Marketing, and Customer Success These teams need to work as one unit. A good RevOps leader will ensure your go-to-market engine runs smoothly and scales effective.

Sales Hiring

SaaStr

JULY 16, 2025

At $549M quarterly revenue (22% YoY growth), they’re proving something important: you CAN still grow 20%+ at massive scale. The “Growth Re-Acceleration” Playbook at $2B+ Scale The Numbers: After moderating to 19% growth in FY2025, MongoDB bounced back to 22% in Q1 2026.

Scale

SaaStr

APRIL 6, 2025

A little ways back Databricks VP of Sales Heather Akuiyibo joined SaaStr to share unexpected things that work well at Databricks GTM organization as well as some things that havent worked as well. Deep Dive: Unexpected Learnings Time Management as Competitive Advantage Most sales organizations guess how reps should spend their time.

Scale

SaaStr

MAY 20, 2025

Convergent evolution from 2 very different start-ups that now have many similarities at scale. Keys to HubSpot’s Success: The “Hub” Strategy : HubSpot mastered the land-and-expand model, starting with Marketing Hub and strategically expanding to Sales Hub, Service Hub, CMS Hub, Operations Hub, Commerce Hub, and Content Hub.

SMB

SaaStr

JULY 11, 2025

Sales isn’t going anywhere in the Age of AI. OpenAI has a big sales team, Windsurf does, Anthropic has a great one. Especially the next generation of them: Perplexity has scaled to 5,000 enterprise customers with just 5 sales reps. Cursor built a $400M business with what appears to be a skeleton GTM team.

Scale

SaaStr

JUNE 24, 2025

We’re living through the biggest transformation in B2B sales since the birth of SaaS itself. The latest from 2025 survey data by ICONIQ from 205 GTM executives across leading B2B SaaS companies The data tells a stark story. This isn’t about sprinkling ChatGPT into your sales process.

Scale

SaaStr

JULY 11, 2025

How Canva’s CCO Built a $7B Enterprise Motion While Preserving PLG Culture Rob Giglio, Canva’s Chief Customer Officer, shares the playbook for scaling from 170M to 230M monthly active users while building enterprise sales without compromising company culture. Top 5 Takeaways 1.

Scale

SaaStr

JULY 8, 2025

Why Founders Stay: The B2B Advantage The 88% founder retention rate isn’t coincidental—it reflects fundamental advantages that founders bring to scaling enterprise software companies. Relationship-Driven Sales Cycles B2B sales are complex, long-cycle, and deeply relationship-driven. Filed, founder CEO.

Scale

SaaStr

JULY 22, 2025

Dear SaaStr: What Are Your Top Tips to Building A First Sales Team? When it comes to sales hires, the key is to approach it methodically and avoid common pitfalls. Always hire at least two sales reps initially. It’s essentially an A/B test for your sales strategy. Trust Your Sales Leaders. You have to A/B test it.

Sales Hiring

SaaStr

MAY 11, 2025

Target 50 great prospects a week and make your outreach personalized and thoughtful. If youre just sending templated emails without understanding your prospects pain points, youre wasting your time. Invest The TIme Here : You need to know who your best prospects are. Instead, focus on quality over quantity.

Scale

SaaStr

AUGUST 4, 2025

Dear SaaStr: What Are The Top 10 Metrics to Track Sales Velocity and Adoption of Our SaaS? To measure sales velocity and adoption rate effectively, you need to focus on KPIs that give you insight into how quickly deals are moving through your pipeline and how well your product is being adopted by customers. Here are the key ones: 1.

Scale

SaaStr

OCTOBER 31, 2024

Here’s what I see most often, the Top 6 Mistakes First Time SaaS Founders Make: Incomplete understanding of business model, and how it will scale. You have to hire those extra few reps that we don’t really have leads for today. Basically I only invest in first-timers. You have to pay folks market.

Scale

SaaStr

MARCH 23, 2025

5 Key Learnings from Scaling from 3 to 75 Go-To-Market Team Members in Less Than 12 Months The latest SaaStr CRO Confidential is out and Sam Blond did a great deep dive with Graham Mareno, VP of Worldwide Sales at Codeium. The 5 Key Elements of Codeium’s GTM Scaling Playbook 1. What is Codeium and Windsurf?

Sales Recruiting

SaaStr

JUNE 25, 2025

AI and Cybersecurity: How Rubrik’s Co-Founder Built a $1B+ ARR Platform While Joining the AI Revolution Lessons from Arvind Nithrakashyap, Co-Founder and CTO of Rubrik, on scaling cyber resilience platforms, building multiple product curves, and implementing AI across both products and operations.

Cybersecurity

SaaStr

JULY 26, 2025

Jonathan Vassel, CRO at Toast helped scale the company from $20M ARR in 2017 to $1.7B+ ARR in Q1 2025 and a stunning $25B market cap. Toast’s CRO Jonathan Vassel shared fascinating insights on how vertical SMB sales is fundamentally different—and why those differences can become massive competitive advantages.

SMB

SaaStr

JULY 26, 2025

A deep dive into one of SaaS’s most dramatic NRR transformations and what it teaches us about scaling retention in the SMB/mid-market When HubSpot filed for their IPO in August 2014, their S-1 revealed a sobering metric that would have made many investors pause: an 88.6% annualized subscription dollar retention rate. 2023: 103.9%

Retention

SaaStr

AUGUST 4, 2025

The Redpoint Playbook: How Top VCs Are Really Investing in AI Applications (And What It Means for Your SaaS Strategy) From SaaStr AI Wednesday with Jacob Efron, Managing Director at Redpoint Ventures If you’re building in B2B today and haven’t figured out your AI strategy, you’re likely falling behind. valuation) and Lorra.

AI Search

SaaStr

AUGUST 2, 2025

Bottom Line Up Front: Applying Figma’s current revenue multiple to Canva’s superior scale, Canva could realistically target an IPO valuation between $195-210 billion , representing a 65-70x revenue multiple similar to Figma’s post-IPO trading multiple. Canva’s aggressive AI investments position it for this premium.

Scale

SaaStr

JULY 14, 2025

CMO-to-CRO reporting is relatively rare (5-10% across all company sizes) despite more and more discussion on LinkedIn and otherwise about how marketing should report to sales for better alignment. Several of my top investments have 2 parallel marketing orgs now at scale, in essence. Top 5 Key Learnings 1.

Scale

SaaStr

MARCH 15, 2025

It’s live on SaaStr.com itself and you can also access it here and talk to AI Jason about any of 1000s and 1000s of B2B, sales, SaaS, VC, etc. Here are some of the top ones: “How My VP, Sales Doubled Our Sales in 90 Days. Here are some of the top ones: “How My VP, Sales Doubled Our Sales in 90 Days.

Sales Hiring

SaaStr

APRIL 5, 2025

But how did they scale so quickly? Here are the five channels that worked for Rupa: Search Engine Optimization (SEO) Social Proof and Trust Building Educational Partnerships and Rupa University Conferences and Event Sponsorships Outbound Sales and Data Quality Lets dive into each. Its about creating high-quality content at scale.

Scale

SaaStr

NOVEMBER 27, 2024

For restaurants, it’s the back end, front end, point of sale, payroll, ERP, and workforce management. Mangomint has one onboarding manager for every two sales reps, but with no contracts and a 30-day free trial, onboarding starts during the trial. Most sales reps hate it. There will likely be multiple Toasts for SMBs.

SaaS Payments

SaaStr

JULY 29, 2025

How are actual revenue leaders at scale implementing AI today? He’s leading Monday.com’s implementation of AI-powered deal desk assistance and automated engagement mapping. His team has been pioneering automated CSM engagement tracking and customer intelligence aggregation at scale.

AI Search

SaaStr

OCTOBER 13, 2024

I try to work with (and invest in) CEOs that are better than me. Or didn’t want to do sales. She should hire leaders for Sales, Marketing, Engineering, Product and Customer Success, or at least most of them. But now, I see that if you can hire a great COO as soon as possible after that, you can scale faster.

Sales Hiring

SaaStr

JULY 6, 2025

This extreme revenue concentration shows Figma’s ability to create significant value for mid-market and enterprise customers—a small number of deeply engaged accounts drive the majority of revenue, indicating strong product-market fit at scale and pricing power within larger organizations. The B2B IPO of The Year?

Software Review

SaaStr

JULY 22, 2025

What Separates Future Decacorns The companies that will break through the $10 billion barrier share specific characteristics that go far beyond traditional SaaS metrics: Scale Requirement s True decacorn candidates operate with 500-2000+ employees and demonstrate the ability to scale operations across multiple geographies and market segments.

AI Search

SaaStr

NOVEMBER 19, 2024

I see too few SaaS start-up and scale-ups truly segment churn. Finally, use NPS as a leading indicator. But I’d say 90% of SaaS companies I work with and have invested in don’t get these basics right for a long, long time. Because churn is the one thing everyone in the company can impact, on some level. Second, segment churn.

Churn

SaaStr

JULY 10, 2025

These weren’t cold prospects — they were website visitors, past attendees, and folks who had engaged with us before. When prospects responded to our AI, I had to respond instantly — and at the same quality level as the AI. Create Dynamic, Customized Follow-up Materials Stop sending generic sales decks. People know us.

AI

SaaStr

JUNE 7, 2025

The shift from “innovation budget” to “operational budget” means AI tools must compete directly with established software investments—and many aren’t winning those comparisons yet. Many organizations are stuck in “pilot purgatory”—running successful experiments but unable to scale them.

AI