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Lessons from Ron Gabrisco, CRO at Databricks, who joined when the company had less than $1M ARR and helped scale it to become one of the largest pre-IPO companies in the world. As CRO of Databricks, he’s built one of the most successful developer-focused sales organizations in the world.
Dear SaaStr: What Quota Should I Give to my EnterpriseSales Reps? For enterprisesales reps, quotas typically range from 3x to 5x their fully burdened on-target earnings (OTE). The exact number depends on your deal size, sales cycle, and how mature your sales process is.
GitHub, founded in 2008, is a leading platform for software development and version control that has made waves since 2018 with its AI Copilot. At this year’s SaaStr AI Summit, GitHub CRO Elizabeth Pemmerl shared how to bring AI products to market at scale successfully. The next horizon is scaling.
Samsara was intentionally multi-product from the earliest days, and they carefully planned out scaling 5+ products to $100M+ ARR. At Samsara, they formalized this with practices like “Transportation Tuesdays” where 20% of sales capacity focused on transportation verticals.
Speaker: M.K. Palmore, VP Field CSO (Americas), Palo Alto Networks
In most cases, the COVID-19 crisis has sped up the desire to engage in digital transformation for medium-to-large scaleenterprises. Preparing for crises that lead to security threats. Roadmaps are rarely implemented without challenges. In this webinar, you will learn: The future of data security. And much more!
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.
Not because of the mistake itself, but because of what it revealed: his AI-powered sales system wasn’t actually being audited by humans. And in B2B sales, that’s a fatal flaw. The AI Sales Paradox Here’s the thing—AI in sales can be absolutely transformative. 90% accuracy sounds great in theory.
Dear SaaStr: What are the most common mistakes first-time founders make when building enterprisesales teams? The most common mistakes first-time founders make when building enterprisesales teams are surprisingly consistent. Heres the breakdown: Hiring a VP of Sales Too Early : This is a classic.
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 enterprisesales without compromising company culture. Top 5 Takeaways 1.
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.
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.
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.
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. New Startups and Companies and Enterprise Strong. So the latest SaaS leader to cross $1B ARR is Klaviyo. SMB Weaker.
Julie Iskow, CEO of $600m+ public SaaS leader Workiva joined Norwest Venture Partners Sean Jacobson at SaaStr Annual for a deep dive on going More Enterprise. Just look at the numbers: Enterprise customers bring 95%+ best-in-class retention vs. 85% in mid-market. Waiting too long to start their enterprise planning.
✨ 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.
Dear SaaStr: What Are Some Successful SaaS Leaders Without Sales Teams? Many that are self-serve and SMB-focused can start off without a sales team … for a while. But almost none stay without a sales team … forever. Yes, Atlassian since well past its IPO had almost no direct sales team. Maybe on Day 0.
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.
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.
It’s an incredible look back on scaling and more: Colin Jones, first Chief Revenue Officer at Wiz. Rather than seeing this as a liability, Wiz leveraged it as a strategic advantage — even in its sales team. Colin joined Wiz in February 2021 when the company was near zero revenue.
These outcomes might include: Driving user growth Maximizing revenue Ensuring user satisfaction Scaling adoption A different outcome would lead to a different pricing choice. Growth stage: Introduced business plans with 20-user minimums to provide enterprise-grade features.
Both started SMB (Monday even more so), and Both have now gone more enterprise (Monday even more) But still with the vast majority of their customers SMB. Convergent evolution from 2 very different start-ups that now have many similarities at scale. Their ecosystem extends their reach globally. Its not either / or.
The Trend Continues: Almost 90% of B2B IPOs Have Their Founders Still as CEO Why founder leadership through public markets remains the overwhelming norm in enterprise software The data is unequivocal: when B2B software companies go public, they almost always keep their founders as CEO. Filed, founder CEO. The market pattern suggests: #1.
That ties to our overall rough sales cycle data here: Dear SaaStr: What’s a Good Benchmark for B2B Sales Cycles? And a few other data from the report: Gongs enterprise customers see about a 25% win rate, conversion from Opportunity to Closed. Thats a bit higher than I expected.
The Enterprise-First Strategy That Worked While OpenAI captured headlines with consumer ChatGPT adoption, Anthropic quietly built an enterprise juggernaut. Gross Margins at Scale AI infrastructure operates with different margin profiles than traditional SaaS. Anthropic did $1B to $4B in seven months.
From Sales-Led to Product-Led: How Apollo.io This analysis examines their journey from a struggling sales-led organization to a successful product-led growth company, resulting in over 880,000 paying customers and substantial revenue growth.
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.
It’s been around for decades but has continued to iterate, expanding into the enterprise, the contact center, and so much more. Even With a Big Enterprise Push for Years, 60% of Revenue Still From Mid-Market and SMB RingCentral closed 20 $1M+ TCV deals last quarter. A reminder to not stay too reliant on direct sales as you scale.
Dear SaaStr: How Do I Hire a Great First 1-2 Sales Reps? "Never, ever hire a VP of Sales until you have 2 individual sales reps really closing. . "Never, "Never, ever hire a VP of Sales until you have 2 individual sales reps really closing. And that early sales team? Hitting quota.
The very best companies lead their customers in that dance. Many mid-market software companies price with the goal of revenue maximization, negotiating for the highest possible price in each sale. Penetration pricing leads to land-and-expand sales tactics. Most startups play defense when discussing pricing with customers.
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.
✨ Lemkin (@jasonlk) July 1, 2025 While everyone’s watching the flashy AI startups and hyperscalers duke it out, two enterprise software giants are quietly crushing it in the Age of AI. Yes, your grandfather’s enterprise software company is crushing it in the age of AI. The Revenue Reality Check: Total revenue of $15.90
So Okta rose to rapid growth and IPO as the stand-alone leader in enterprise identity for apps, acquired Auth0 to own it for developers, and now coming up on $3 Billion in ARR, it has settled into a more mature state: $2.75B in ARR Growing 12%, projected to slow to 10% Non-GAAP operating margins of 27% Free Cash Flow margins of 35% (!) $18B
Typically, you’ll want to show 7%-15% month-over-month growth leading up to the raise. This shows you have a scalable and efficient sales model. If you’re selling to mid-market or enterprise, negative churn (expansion revenue outpacing churn) is a strong signal. Churn : Low or negative churn is critical. Just be aware of it.
When Lindsey joined, she inherited an already built-out self-serve/PLG model for small businesses and a mid-market and enterprisesales, customer success, and post-sales team. But at the start of its expansion play, Checkr’s enterprise motion failed, and sales cycles were slow, taking up to a year for $100k & up deals.
What “Working” Means in the Era of AI Apps: The New Enterprise Benchmarks That Matter One of the most common refrains in the generative AI era is that “startups are growing faster than ever” — often with fewer resources. But for the average enterprise AI company (not the top 0.1%), what does growth really look like?
Even more telling: these large customers represent 37% of total ARR , showing Figma’s ability to expand within enterprises far beyond initial design team deployments. This penetration-to-monetization gap indicates enormous expansion potential within existing enterprise customers. The 80/20 Rule on Steroids: Just 2.5%
Dear SaaStr: How Should I Build Our First Sales Comp Plan? Creating a sales commission plan is critical for motivating your team and aligning their incentives with your company’s goals. This can start off higher in the very beginning, but at scale is generally around 7%-10% of the deal. Commission : 10% of ACV for new deals.
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?
Happy customers lead to renewals, upsells, and referrals, which are the foundation of B2B growth. Don’t Rely on Sales to Handle CS Sales reps are great at closing deals, but they’re not built to manage ongoing customer relationships. Avoid the mistake of expecting your sales team to handle CS responsibilities.
Thread AI’s founder and Palantir alum Maya Gonimah has cracked the code on enterprise AI implementation through their strategic partnership with Google Cloud. Darren Mowrey (Google Cloud) Darren leads strategic partnerships at Google Cloud, focusing on helping startups scale their AI implementations.
Meet Wyatt Jenkins: From Construction Sites to Chief Product Officer If you want to understand how vertical SaaS companies scale to $1B+ in revenue while staying true to their customers, there’s no better person to learn from than Wyatt Jenkins, Chief Product Officer at Procore Technologies.
Dear SaaStr: How Should I Specialize My Sales Team? One thing is clear: most founders and VPs of Sales and CROs look back and wish they’d specialized their sales team earlier. And not have everyone work in a round-robin or similar format on all the leads, just split across their reps.
Enterprise Companies (1000+ employees) : The most distributed structure emerges. 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. Top 5 Key Learnings 1.
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.
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