Why Hiring From Your Direct Competitors Usually Doesn’t Work Out
The time will come when you are first tempted to hire someone from your competitor. They must know so many things we don’t. Have so many skills. It’s pretty tempting. People will tell you about the risks in litigation, trade secrets, etc. I don’t think any of those are necessarily a big deal or a [...]
5 Non-Obvious Things To Know About VCs
I was catching up with a VC friend the other day and asked him about a company I’d referred to him. They’d passed on the investment (which is of course fine), despite the company meeting basically every investment criteria I knew about the firm. I asked the partner why. His answer was simply — timing [...]
My Favorite Entrepreneur Story in a Long Time
If you don’t like it hot, use less,” he said. “We don’t make mayonnaise here.” This morning I was reading my social media and came across an article that Christine Tsai had posted on Facebook. It was about the founder of Sriracha sauce, David Tran, displaced from Vietnam when the North’s communists took power. As the son [...]
Stop Trying to Catch Lightning in a Bottle
I’m sure you’ve all heard saying derived from Voltaire, “don’t let perfect be the enemy of the good” which in a way is encapsulated in the lean startup movement and the ideology of shipping a “minimum viable product” (MVP) and then learning from your customer base. Or to borrow a simple life lesson from Gretchen [...]
In SaaS, You Have to Love the One You’re With
Recurring revenue businesses are hard. You need so many different types of people (sales, support, client success, demand gen, product, engagement, dev). The customers complain, especially your most loyal ones. You have to get on planes. You have to grovel. It’s tough. And for a lot of us … well … it just turns out [...]
How to Sell Your Roadmap Without Selling Your Soul
This is my third post in a series on Enterprise Software. In part one I covered the need for early-stage enterprise software companies to build up professional services staff to ensure successful implementation projects. This goes against the conventional wisdom of VCs. In part two I talked about how to ensure that your professional services [...]
How to Better Manage Relationships with Your VC
Just back from 2 solid weeks on the road in Boston, New York & Philly. I spent countless hours with VC firms, startups & LPs (the people who invest in VC firms). I find these trips invaluable both from a relationship-building perspective as well as stretching my mind about our industry. I ask questions, test [...]
Why You’ll Want to Raise $100,000,000 for Your SaaS Start-Up: The Incremental Customer
With all the SaaS companies raising big, later-stage rounds these days you may wonder … why? I mean, just because you can raise $100m or whatever epic number … should you? Today, I think the answer is yes. Though perhaps not for the reasons you might think. There are a couple of standard reasons companies [...]
The 48 Types of VP Sales. Make Deadly Sure You Hire the Right One.
Oy, the VP of Sales. The toughest hire. Such a high failure rate. I want to help. So this is the third in our series. The first post is What a Great VP of Sales Actually Does. So you expect the right things, and hire your rockstar at the right time to do the right [...]
Day 1: Who Should Be CEO? A Checklist.
SaaStr has now passed 100+ posts, and we’ve somewhat gone on a journey from the early days of a SaaS company, through the growth phases, and as of our last post, up to the Unstoppable phase. We’re not quite done with that journey but if you’ll forgive me going back in time, I wanted to [...]
The $64,000,000 Question: When Things Become Unstoppable
A little while back, a VC asked me what I thought of a prospective mid/late stage investment. I was/am reasonably familiar with this company as it is adjacent to EchoSign. My answer was, well, I’d probably pass — certainly at the valuation (12x+ ARR). I said the product was ooooold and the platform dated, the [...]
When Big Companies Can Kill You. And When They Can’t.
I remember every day, every moment, of both my start-ups with hyper-lucidity. But a few moments especially stand out. Those times when BigCo calls you up to their fancy office, and tells you they are going to enter your space and kill you. It happened to me twice at EchoSign. I’m not going to share [...]
How to Make Sure Professional Services Don’t Take Over Your Software Company
I recently wrote a blog post in which I pointed out that many investors & advisors discourage enterprise startups from having a professional services (PS) business and I think this is a big mistake. I think it’s important for enterprise startups to layer in professional services into your revenue stream. PS capabilities are important for enterprise [...]
Things Not to Share With VCs (and Others) Pre-Term Sheet
In the pre-diligence phase with either VCs or acquirers, I’ve learned you want to hold some things back. Not through the whole process. But at least until you are past the Second Date.
One of the Biggest Mistakes Enterprise Startups Make
The era of VCs investing in successful consumer Internet startups such as eBay led to a belief system that seemed to permeate many enterprise software startups that hiring sales or implementation people was a bad thing. “We want low-touch or zero-touch businesses” was the mantra. I believe it’s flawed. While I have some sympathy with [...]
