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What’s The #1 Challenge After $1m-$2m ARR?

SaaStr

Upsell and retention is an art, science and craft. You can smother customers with love alone in the early days, but as you scale, you need a seasoned customer success team and VP that has done this before. Or churn will increase, NPS will stagnate and decline, and upsell and revenue retention will be a fraction of what it could be.

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Dear SaaStr: What’s The Number One Challenge for Scale-Up Stage Founders?

SaaStr

Upsell and retention is an art, science and craft. You can smother customers with love alone in the early days, but as you scale, you need a seasoned customer success team and VP that has done this before. Or churn will increase, NPS will stagnate and decline, and upsell and revenue retention will be a fraction of what it could be.

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5 Interesting Learnings from Okta at $2.5 Billion in ARR

SaaStr

Founder CEO Todd McKinnon was VP of Engineering at Salesforce and left to start Okta in the depths of the last downturn. Seat Contractions Have Brought NRR Down From 120% to 111% While 111% NRR is still quite an engine at this scale, the drop in NRR from seat contractions explains a good chunk of the headwinds Okta has seen. #2.

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The Founder’s Guide to Developer-led Growth with WorkOS (Video)

SaaStr

They’re able to actually swipe a credit card, and what starts off similar to a freemium self-serve product can turn into a six-figure contract in just a few months. It might even be months later that a VP of Engineering or a CTO or CFO realizes that they’re built on a new platform. The contract size grows.

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25 predictions for SaaS in 2025

Chart Mogul

Polis Pilavas , VP of Engineering at ChartMogul SaaS will shift to real-time personalization, enhancing individual user experiences by learning from every interaction, in an attempt to boost retention, increase satisfaction, and drive growth. Companies will scale faster with flexible solutions replacing rigid legacy systems.

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Dharmesh Shah of HubSpot: From Day 0 to IPO. What Went to Plan. What Most Certainly Didn’t (Video, Podcast + Transcript)

SaaStr

Hire the VP of Marketing, MBA, the VP of Sales, MBA, the VP of Customer, MBA, the VP of Engineering, MBA, and now, the odds of any semblance of survival, let alone success, are vanishingly small at this point. The issue the SMBs had was, “Well, I’m a 20-person consulting company.

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Engineering Your Own “Luck”: The 3 Key Rules of Building Globally Distributed Teams with Eventbrite (Video + Transcript)

SaaStr

Building a company made up of distributed teams presents a plethora of complex challenges that can derail productivity and impact employee retention. I started right at the end of 2011, and I started in the role of VP of engineering. The best thing is retention in these offices has been just amazing.