
The Two Things to Do. When You Don’t Know What to Do.
There may come a time, or two, in your company when you just don’t know what to do. You aren’t growing fast enough. or The competition seems to be getting the best of you. or You can’t raise financing. or You just lost an important deal. Or maybe more than one. or That great new […]

Why The Law of Large Numbers is Just an Excuse
Everyone has tough quarters, and usually, at least one tough year (more on that here). As we approach $10m, and then again as we approach $20m, and then again as we approach $X0m … we often blame a factor that I believe rarely is really real — The Law of Large Numbers. The Law of […]

The Top 10 Worst Pieces of SaaS Advice
Advice is very context sensitive, so take this post with a grain of salt. But for me, it’s “Blue Monday” … so I thought I’d take a stab at the Top 10 Pieces of Classic SaaS Advice … that in my experience at least are usually Just Plain Wrong. The advice and thinking that leads you […]

My First Big Sales Deal
In my first start-up, I was mostly hunting whales — seven figure and eight figure deals. I had no experience doing any of this. For our First Big Customer, we’d been negotiating a $6m/year contract for quite some time (they always take time). We finally had the “all hands” meeting with all the C-level and […]

Dharmesh Shah of Hubspot: From Day 0 to IPO. What Went to Plan. What Most Certainly Didn’t (Video + Transcript)
In anticipation of the upcoming SaaStr Annual 2017, we’ll be releasing the full series of transcripts and videos from all the awesome 2016 sessions. There are rules in starting an enterprise software company. You will fail if you: 1) try to build a suite of products out of the gate, 2) focus solely on SMBs, or 3) […]

Small Deals at Large Companies. Hooray!! And 100% At Risk.
Every customer you close, the next day, is at risk of churn. A month-to-month customer can basically cancel anytime. An annual contract customer can sort of cancel anytime, but really probably won’t for a year, or even 3 (more on why Year 3 is the biggest risk for bigger customers here). You know this, of […]

Cornerstone OnDemand’s Kirsten Helvey: Scaling from 30-1,500 in SaaS: Lessons From the Frontlines (Video + Transcript)
In anticipation of the upcoming SaaStr Annual 2017, we’ll be releasing the full series of transcripts and videos from all the awesome 2016 sessions. In this session, Jason Lemkin receives some valuable insight from Kirsten Helvey, COO of Cornerstone OnDemand, a cloud-based learning and talent management solutions provider. Drawing from her 11 years of experience […]

When the Player-Coach is Just That. And No More.
We’ve talked a lot on SaaStr about not screwing up that VP of Sales hire. Done right, it will accelerate your company to the next level. Done wrong — you can lose the better part of a year, and half of your last round of capital. And we’ve talked a lot about the trade-offs in […]