When to Stop Doing It All Yourself
Perhaps the biggest difference between most first-time founders and most second-time founders is how long they try to do it all themselves. This isn’t a criticism first time you usually sort of have to. You have less capital to hire a team, and less experience building teams. But then after that there are at least […]
One Simple Rule on When to Build a “Custom” Feature
“Custom” features … I feel this is perhaps the point founders get the worst advice of all. Especially from VCs, B2C folks, and folks that have never sold bigger deals and into the enterprise. One-off customization per se is bad. This is SaaS, not a services business. But Being paid a lot to build something […]
Last Minute Tips & Tricks for The SaaStr Annual!
It’s almost here. The 2017 SaaStr Annual. Just a few extra last minute tips: It Will Be Packed. We’ll have ~10,000 nominal attendees which realistically means about 5,000 on-site at any given time at the Bill Graham (not everyone will be there at all times, etc). The Bill Graham is a super fun venue, the […]
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 […]
Time Doesn’t Kill All Deals. But It Puts Them At Risk.
There’s a little bit of death-by-a-hundred cuts that many SaaS companies box themselves into. As they scale, they get out of the hackey way they do contracts, NDAs, proposals, and other documents. They have their controller, then their VP of Finance, then their CFO review things, then hand off to the General Counsel. Which takes […]
A Newbie’s Guide to Dreamforce. Hint: You Can Go For Free. And You Will Learn at Ton.
Next week is the largest SaaS event on Planet Earth: Salesforce’s Dreamforce. (The SaaStr Annual ’17 will be #2). I’ve been going since 2005, from ’06-’11 as a vendor, and ’12-today as a participant / speaker / etc. I went first in ’05, when I knew nothing about SaaS. Back then, I think it just […]
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 […]
e-Staff Meetings and 1-on-1s: You Gotta Do Them
For the first time in my career, I’ve worked with amazing first-time managers as CEOs. Before I was a CEO, I was a mid-level manager, a director. And then a VP. Across a few start-ups. Before I was first a founder. Those management team weren’t perfect, and I wouldn’t copy everything they did. But at […]
The Easiest Ways to Get From $1M ARR to $10M ARR
The most important thing is not to chase the shiny penny, assuming you are growing at least 60% Year-over-Year. You’ve done the Impossible. You’ve gotten 50, 100, whatever # of businesses to pay you $1,000,000 a year. There are 10,000 new apps out there. It’s “impossible” to get to $1m. You did it. Now, the […]
Faking Being in the Bay Area
There’s an endless and lively debate about the advantage of being in the SF Bay Area in SaaS. I’ve done 22 investments. The vast majority got started outside of SF, and all but 2 moved here. I’ve invested in founders from Paris (3x), Estonia, Portugal, London, Sweden, Belgium, Washington D.C., Chicago, New York, and more. […]
Don’t Let Them (Your Best Employees) Go
Now that a handful of next-generation SaaS companies have IPO’d, you can start to see the turnover more viscerally that you can observer at quieter, privately-held start-ups. You see the VPs moving on. 6-12 months after almost any IPO, and especially after one that doesn’t create a slew of millionaires … folks leave. It’s a […]
So Your App Is Just a “Nice to Have”
In the old days, folks would criticize start-ups as “just a feature”. Oh Google/Salesforce/Microsoft will just build that. Back in the day when the world was a desktop OS, there was a lot of truth to that. When the web became our OS, that started to fade. The reality is, in SaaS, Salesforce has built […]
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 […]
Marketo: Winning, IPOing, and Going Upmarket (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. We were super excited to have Phil Fernandez, CEO and co-founder of Marketo, sit down and talk to us about the triumphs (and struggles) leading Marketo from inception to IPO. Phil […]
