
Aaron Levie of Box: “If We Just Sold to Silos-in-the-Enterprise, We’d Only Be a $25,000,000 Business”
Missed the 2015 SaaStr Annual? We’ve got your back. We’ll do a series where we publish both the videos and full transcripts of all the sessions. First up is Aaron Levie of Box, where we had a wide-ranging, 45 minute deep dive on how Box scaled from $0 to $250m in ARR. As you’re reading […]

SaaStr Podcast on Time, Core Metrics and More on “Million Dollar Insights”
Do you podcast? If so, Cara Hogan of InsightSquared has kicked off a great SaaS podcast series of which I was fortune enough to participate. We talked quite a bit about the learnings on the SaaS Journey. Feel free to listen below or download on iTunes here. The draft notes and script I used (we went […]

One Weird Trick to Build a Personal Brand
My long-time friend Jason Lemkin is on the verge of launching a spectacular SaaS conference called SaaStr this week. What Jason has achieved in no time flat in VC is astounding. Without inventing the browser he has single-handedly created a personal VC brand on a shoestring. And as I’ve written about before – building a […]

All These Enterprise IPOs: Why It’s Just Getting Good. Why These are The Best of Times for SaaS.
Reading the tech press you might get the sense that The Enterprise is something they are sort of forced to write about because it’s having a good run. We had a great Consumer run, a nice set of Multi-Billion Dollar deals around Social Networking, a WhatsApp/Snapchat fad around mobile messaging, an Alibaba, Instacart, Fab-ulous e-commerce […]

The Low Viral Coefficient of SaaS, And Why That’s Just Fine
We’ve talked a lot on SaaStr about how to get from $1m to $10m, $2m to $5m, $10m to $30m, etc. etc. One area we haven’t talked as much about is getting from say $100k in ARR to Initial Traction, or $1-$2m in ARR. A bit, but not as much. The reason is while I […]
SaaStr on NBC’s Press:Here on Box, DropBox, WhatsApp — And the Lack of Fear
NBC was kind enough to have us back on Press:Here (right after Meet-the-Press) to discuss DropBox’s almost-$1-billion in debt and equity raised this year, Box’s IPO, and beyond that, just what’s Going On in the Enterprise these days. My overall answer: there’s current a Lack of Fear, notwithstanding the (relatively modest) market correction in ’14. […]
The Simple Reason Why There Will be 10-20 Great CRM IPOs in the Next Few Years
I wrote a while back about Room at The Bottom, and how once a space gets big enough (~$100m) or so … the biggest guys end up abandoning many of the smallest customers and segments in their space. Which once a space is at, say $100m in market size, can open up a $10m hole […]

I’m Presenting at Dreamforce. Right Before Marissa Mayer. Come See the Hottest Two Speakers at Dreamforce ’13.
OK maybe SaaStr doesn’t quite have the following of Marissa Mayer. But it’s a solid pairing, don’t you think? In any event … If you are in SaaS and haven’t been to Dreamforce before, let’s stop the discussion here: You Should Go to Dreamforce. You need to Go. Why? Dreamforce is the #1 largest SaaS […]

Stop Ignoring Terms and Conditions in the Cloud
Check your T&C’s as you could be handing over your creative work for free.

Rethinking IT Transformation for the Cloud
As cloud computing matures and success models emerge, enterprises are now getting serious about using cloud to drive IT transformation. JP Morgan Chase, Toyota, GE and other leading organizations are moving beyond incremental costs savings and are using cloud and next generation platforms to drive innovation, growth and competitive advantage. Unfortunately many CIOs and their […]

Why "Enterprise SaaS" may soon be a misnomer
One of the most exciting developments to hit the enterprise software world in decades was the rise of SaaS. Companies like Salesforce.com blazed a trail that built enormous amounts of wealth and improved the lives of end-users. Prior to SaaS, most enterprise software was sold based on perpetual licenses, to CIOs and IT departments, with […]

Quick Note: Dropbox – Mailbox Marriage Is A Hail Mary Pass
This morning an acquisition news got techies excited about Dropbox buying the iOS app with lots of buzz but few invites, Mailbox. In short, this is a hail mary pass after Google announced that you can now attach large attachments with Google Drive integration in Gmail. Dropbox had to react and they reacted by buying […]

Box Answers IT Concerns–Deeper Security Option Roll Out
Just a couple of weeks ago I wrote about Dropbox releasing an entire swathe of new security functionality that sees it firmly mark itself as entering the corporate market and responding to the needs of IT. As I said at the time, Dropbox has long signaled an intention to move up the food chain. In […]

Celebrity Engineers–Software’s Equivalent of Arts Patronage
Back in the days gone by, if you were part of the landed gentry, lording over your landholdings and the common folk who lived on said land, you’d look to becoming a patron of the arts as a way to ensure your name would live on after your death. While perhaps not a particularly sound […]

Dropbox Listens to the Criticism–Starts to Mature Corporate Product
I’ve been a harsh critic of Dropbox in the past – mostly because I feel they lack maturity – both as a company and as a product – and this lack of maturity is a real risk for enterprise customers using their product. It seems Dropbox has been listening to the criticism that myself and […]