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Dear SaaStr: How Much Should a SaaS Company Invest in Professional Services? A rough yardstick is that most enterprise-focused SaaS companies tend to get about 8%-10% of their revenues from professional services. Salesforce similarly on the enterprise side has built a huge ecosystem to do the services work for them.
Dear SaaStr: Why Do Enterprise Customers Insist on Pilots? Because so many enterprise customers won’t buy from new start-ups without a pilot. This reduces the perceived risk of adopting a new solution, especially if theyre replacing an existing system or investing significant resources. Risk reduction is key.
✨ 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. SAP restructured 10,000 positions to fund AI investments.
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.
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.
Andreesen Horowitz recently pulled some great data from the deals its invested in and looked at. 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.
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.”
“The Last Generation of Human-Only CEOs: Marc Benioff’s Bold Vision for the AI-Augmented Enterprise” Marc Benioff was kind enough to join SaaStr for the first time to do a truly deep dive on what AI means in business software today. It’s a good one. Top 5 Unexpected Learnings: 1.
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. This isn’t a demo—it’s enterprise-grade monitoring and analytics.
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. Bold Marketing Investments : The company’s aggressive marketingincluding their memorable Big Game adhas built massive brand awareness. Its not either / or.
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. Klaviyo is seeing strengths in its entrepreneur segment (new companies) and enterprise ($50k+ deals) as noted above. Just not as quickly as overall revenue growth. #4.
The Great Spending Showdown: AI vs SaaS in 2025/2026 — What Every B2B Leader Needs to Know We’re witnessing the most dramatic shift in enterprise tech spending since the cloud migration began 15 years ago. The answer today is: very few. But that could change rapidly as AI tooling improves and more case studies emerge.
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.
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%
Many of the companies Ive invested in only offer annual pricing. But in the case of true enterprise applications, where you are changing the way entire companies work, you usually have business process change to manage. The real downside to annual billing is the quid pro quo in the early days is often a pilot first in the enterprise.
Company Snapshot: Founded : January 2014 (11 years) Current ARR : $1.09B+ (Q1 FY2025) Growth Rate : 39% YoY ARR growth, 47% revenue growth NPS Score : 80 (exceptionally high for enterprise software) Net Revenue Retention : 133% (as of Jan 2024) Customers : 2,246 customers with $100K+ ARR contracts IPO : April 2024 on NYSE (RBRK) at $5.6B
The Deceleration Evidence Ramp’s card spend data reveals several concerning trends that suggest the AI adoption curve is indeed slowing: The growth rate from Q4 2024 to Q1 2025 was significantly lower than previous quarters, even accounting for typical seasonal variations in enterprise spending. ROI scrutiny is intensifying.
commercial revenue surged 71% as Artificial Intelligence Platform (AIP) gains enterprise traction Deep government/defense roots benefit from heightened geopolitical tensions worldwide Clear AI differentiation has made it indispensable for data-driven decision making How AI Led Palantir From Slow Growth (13%) to Hypergrowth (49%!)
Friedman brought deep experience in developer tools and enterprise software from his time leading GitHub through its acquisition by Microsoft and subsequent growth. ✨ Lemkin (@jasonlk) July 4, 2025 Financial Infrastructure: Basis Basis represents NFDG’s investment in the accounting and financial software space.
So two of the great leaders in SMB SaaS, Shopify for e-commerce, and HubSpot for sales, marketing and more, are going more upmarket: HubSpot 100+ seat deals are up 55% Shopify now gets 31% of its revenue from “Plus” or its bigger brands and more enterprise product And yet … they are also both going more SMB as well!
Traditional VCs usually reserve another 1x-2x of their first check for later investments. If the synergies are real, they’ll happen irrespective of some token investment. An investment won’t create a partnership. An investment may anoint one vendor in the space as the preferred vendor over competitors. Be realistic.
Okta’s VP of Engineering, Monica Bajaj, and Senior Director of Platform Product Marketing, Priya Ramamurthi, share Okta’s playbook to PLG, developer experience, and Enterprise ARR. What does scaling Enterprise ARR mean? The Enterprise Funnel Finally, it’s time to scale as your experts become advocates and champions.
So theres a theme Ive been working on with all the SMB-focused founders I work with and have invested in: # 1. Easy in enterprise, hard in true SMB. # Your job is either to go much more enterprise to get to 100% NRR or to make your product into the OS for an SMB. The Goal for SMB SaaS is 100%+ NRR.
Dear SaaStr: How Do You Become Successful at Enterprise Sales? If you haven’t done enterprise sales before, the biggest thing to understand: you can do it. But for enterprise sales, you’re going to have to get your arse out of your home office and go close some real live human beings: Listen — often in person.
Having led sales teams of 500+ at BILL and 800+ at HubSpot, Michelle has unique insights into what makes great frontline managers and why investing in them is crucial for sustainable growth. “Some teams consistently sold more enterprise SKUs, others had high volume but low ACV. ” The bottom line?
GTMfund’s 3 Areas of Focus for Investing Thanksgiving weekend is always a period of reflection and gratitude. Reflection across go-to-market trends, but also on the investment front (not to mention community !). A common misconception is that the name is representative of the type of software we invest in.
Several macro factors are converging to create this perfect storm: Enterprise Budget Scrutiny : CFOs are demanding higher ROI thresholds for software investments. The low-hanging fruit of digital transformation has been picked, and companies are being more selective about additional software investments.
It’s the emergence of a new category that’s attracting billions in investment and fundamentally disrupting the $500B+ software development market. Enterprise-Grade at Scale Major companies like Zillow and HubSpot use Replit for production systems. And allowing more experienced developer to ship far, far faster.
SMB, mid-market, enterprise). Benchmark Your GRR : Investors will compare your GRR to industry standards: Enterprise SaaS: 90-95% Mid-market SaaS: 85-90% SMB SaaS: 80-85% Anything below these benchmarks signals potential retention issues 3. For enterprise customers, this should be closer to 12-15% 3.
Organizations that invest heavily in customer success earlier see much higher customer retention and loyalty than the competition. But you have to be intentional and clear on what and where you want to invest to drive that high-value impact. For example, say your company is going upmarket to Enterprise.
Mid-Market Is The Perfect Laboratory For Both Product and Go-To-Market Development Most founders falsely view market segmentation as a binary choice between SMB and Enterprise. Yet they close in months, not years, with substantial ACVs ($20-70K+) that support full sales motions including SDRs, AEs, and CSMs.
Data-Driven Learning #3: Enterprise Penetration = 78% Moat Depth The Data : 78% of Fortune 2000 adoption rate with 132% net retention. The key is concentrated investment in differentiation, not diversification. average revenue per customer over lifecycle The Strategy: Don’t build horizontal. Build workflow-adjacent.
Their return demonstrates their continued investment in the SaaS ecosystem and commitment to helping founders succeed. Pylon – Welcome Back for Round Two! 🚀 We’re equally excited to welcome back Pylon as a 2nd-time sponsor of SaaStr Annual!
This isn’t just a comeback story—it’s a masterclass in how enterprise software companies can reinvent themselves when new technological waves create fresh demand for their core capabilities. That’s exceptional performance for any SaaS company, let alone one dealing with complex enterprise deployments.
So this may seem like a pretty specific post, but it’s a big and real issue I see so, so often these today in SaaS companies at scale, from $20m-$200m+ ARR: They’re reacting to tougher times by going “more enterprise” That can make a lot of sense. I hear this again and again. appeared first on SaaStr.
This consumer base provides: Brand recognition : ChatGPT has become synonymous with AI for many users Data flywheel : Millions of interactions improve model training Market validation : Consumer enthusiasm drives enterprise interest Revenue diversification : Both subscription and API revenue streams Anthropic’s Enterprise-First Approach Anthropic (..)
It’s now falling to 150 because 81% percent of the dollars invested in venture capital at the height of the boom came from non-traditional venture capital firms which are all very likely to leave investing. So, if an executive wants Enterprise software, they can bypass procurement. Why is the mid-market harder?
Elizabeth explained: “We continued doggedly poking at this problem of where else can Copilot help developers be more creative and more satisfied, and so we integrated Copilot then across the command line, across our pull request features, across issues and documentation, and that became the basis for CoPilot Enterprise.”
Despite having spent almost no direct dollars on marketing, they reached 360,000 paying customers at an average ACV of $276—compared to enterprise darlings like Wiz who hit $100M with 260 customers at $384K each. They achieved this with $0 invested in marketing and just 131 employees. The kicker? Build for sharing from day one.
How to Make Onboarding Work for SMBs While in some cases, selling to SMBs is easier than Enterprise in many ways, one way in which it’s fundamentally harder is onboarding. Mangomint has worked hard to create an incentive structure that makes it attractive for sales reps to invest in customer success. Mangomint doesn’t have that.
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. Public markets consistently reward founder leadership. #2.
G2 had us back for another great deep dive on just where SaaS investing is there days, and it was a great panel: Accel Partner Arun Mathew Inspired Capital Founder & Managing Partner Alexa von Tobel Salesforce Ventures Managing Partner Paul Drews and Jason Lemkin! Low investment multiples pose a key challenge.
Enterprise data is the differentiator: While public data dominates foundation models, enterprise-specific data represents less than 1% but delivers exponentially more value when properly leveraged. IBM’s $7B Bet on Vertical AI and What It Means for SaaS Founders.
At Saastr Annual, we hosted an Enterprise panel of AI leaders to share their experience and knowledge to help others understand how big companies think about and leverage AI. While the first generation of Generative AI is great, it’s not quite ready to solve Enterprise problems. What Are Enterprises Most Excited About Using AI For?
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