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 176

Scale Sales Hiring Scaling Revenue 176

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 273

Scale AI Sales Hiring Sales 273

SaaStr

DECEMBER 20, 2024

Former Head of Revenue at BILL and HubSpot Americas leader Michelle Benfer recently joined us on a SaaStr Workshop Wednesday share her insights on one of the most critical roles in any SaaS organization: the frontline sales manager. “At HubSpot, I had over 100 frontline sales managers reporting to me.

Sales Hiring 260

Sales Hiring Scale Underperforming Technical Team Sales 260

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 247

Scale Sales Hiring AI Sales 247

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 185

Scale Sales Hiring Scaling Sales Recruiting 185

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 301

Scale SMB Scaling Enterprise 301

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 194

Scale AI B2B SaaS 194

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 202

Scale Sales Hiring Sales Outsourced Development 202

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 185

Scale AI Headcount Sales Hiring 185

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 273

SMB Scale Education AI 273

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 238

Scale AI Churn Investment 238

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 256

Cybersecurity AI Scale CTO Hire 256

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 175

Scale AI Enterprise Venture Capital 175

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 185

Scale B2B Underperforming Technical Team Leadership 185

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 242

Sales Recruiting Sales Hiring Scale AI 242

SaaStr

SEPTEMBER 11, 2024

Lucid is the leading provider of visual collaboration software with over 70M users worldwide. Stephanie Couzin, the VP of GTM Strategy and Ops, and Roderick De Greef, the VP of Sales and GM EMEA, share Lucid’s transition from a PLG company to a PLG and Sales-Led company. For Lucid, this meant a few things.

Scale 307

Scale Scaling Sales Hiring compliance 307

SaaStr

AUGUST 15, 2024

There’s always someone a few years ahead of you on the scaling journey who can share their lessons learned. Robbie O’Connor, the GM EMEA at Notion and the first European hire at Asana and Dropbox takes the stage at SaaStr Europa to talk about the building blocks required to scale GTM teams and operations. Timing is also essential.

Scale 310

Scale Sales Hiring Scaling Innovation 310

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 307

Scale Social Media SaaS Business Model 307

SaaStr

JULY 6, 2025

Friedman brought deep experience in developer tools and enterprise software from his time leading GitHub through its acquisition by Microsoft and subsequent growth. The duo launched their venture fund in 2023, raising an impressive $1.1 billion in their debut fund—a testament to their combined reputation and track record in the tech industry.

Venture Capital 312

Venture Capital Artificial Intelligence Technical Advisors Scale 312

SaaStr

AUGUST 9, 2024

From startup to $500M CARR, Spencer Burke, SVP of Growth at Braze, shares how Braze scaled a growth and customer success team. In this AI moment we’re in, there are still many moments in scaling a company where intuition still matters. You don’t have to leave as the organization scales. This isn’t new.

Scale 291

Scale Sales Hiring Scaling Startup 291

SaaStr

JUNE 20, 2025

The Billion-Dollar AI Unicorn Factory The scale of AI startup funding isn’t just impressive — it’s existential for SaaS: The AI Billion-Dollar Club: OpenAI : $8.4 billion valuation after 175M round Scale AI : $29 billion valuation / “sale” with Meta’s $14.3 billion in funding xAI : $6.4

AI Search 289

AI Search Artificial Intelligence AI CTO Hire 289

SaaStr

JULY 7, 2025

Unlock Continuous Access to the World’s Highest-Value B2B Decision Makers Forget A-tier prospects. At SaaStr, we deliver S-tier leads—the elite decision makers who control enterprise budgets and drive industry innovation. S-Tier Audience = S-Tier Results Who exactly are S-tier leads? ROI, $47 cost per qualified lead (vs.

Scale 216

Scale Outsourced Development Leadership AI 216

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 260

Sales Hiring CTO Hire Scale Startup 260

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 229

Scale AI Search Sales Hiring Acquisition 229

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 258

Sales Hiring AI Scale Compensation 258

SaaStr

MAY 25, 2024

Cloudinary VP of Developer Experience Sanjay Sarathy shares his journey to more than $100M and the lessons he learned along the way for building a PLG motion and an Enterprise sales motion. They didn’t initially envision being a large Enterprise sales organization. Let’s first start with how Cloudinary came to be. The takeaway?

Scale 312

Scale Sales Hiring SaaS Payments Development 312

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 281

AI Payment Services Payments Scale 281

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 175

Scale Marketing Leadership Branding 175

SaaStr

DECEMBER 22, 2023

At the SaaStr Annual, Kiren Sekar, Samsara’s Chief Strategy Officer and founding chief Product Officer shared five lessons he learned along the way from scaling six products to $100M+. Lesson 1 — The Magic “Scale or Pivot” Metric With so many different SaaS metrics out there, which metric can really steer a business?

Scale 306

Scale Scaling Strategy Sales Hiring 306

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 257

SaaS Payments Payments Payment Solutions Payment Services 257

FastSpring

JANUARY 23, 2025

Listen for the full insights into: How Flippa.com works to connect for-sale businesses with buyers while managing the complexities of valuation and seller expectations. How selling an investment business is very different from getting VC funding. And that’s substantial scale in. That’s now a billion dollar company.

Scale 119

Scale Entrepreneurship Scaling Underperforming Technical Team 119

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 266

Software Review Scale Systems Review Enterprise 266

Clouded Judgement

MARCH 28, 2025

Starting and scaling a software company was really hard. Starting and scaling a software company was really hard. If you wanted to scale users and growth, you needed to scale a physical data infrastructure footprint. ” This used to be how companies scaled! It wasn’t very elastic. What does this mean?

Cloud 299

Cloud AI Scale Scaling 299

SaaStr

JUNE 5, 2025

The New Rules of AI Investing: Why Speed Beats Strategy and Labor Budget Is the New Software Budget The pace of AI advancement has fundamentally broken our traditional frameworks for thinking about technology adoption, market timing, and competitive moats. ” This represents a fundamental shift in venture investing criteria.

Software Review 249

Software Review Technical Review AI Development Team Review 249

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 270

Churn Retention Scale Investment 270

SaaStr

AUGUST 5, 2024

When you find the answer to these questions, you can expand an existing customer base and create cool data-driven case studies to help your sales team bring in net business. 1: Build a Value Narrative Value narratives have been around for some time in pre-sales motions. Often, that doesn’t feed through to post-sales.

Scale 284

Scale Customer Success Scaling Revenue 284