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10 Great Questions to Ask a VP Sales During an Interview

Ready to hire your first VP Sales?  But haven’t done it before? Let me give you a partial interview script that may help a bit.  You’ll have to vary it for different types of SaaS businesses — a bit....

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Your Customer Success Team. Hire Early. And No Squishy Goals — It’s All About...

If this is your first SaaS company, you may not have ever hired or built a Client Success team.  This one isn’t nearly as risky as a VP of Sales, or a VP of Marketing hire.  If you hire a great,...

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3 Tips for Building Discounts into Your SaaS Pricing Model (from OpenView Labs)

The good folks at OpenView Labs did an interview with SaaStr and broke it up into a few articles.  The first they published the other day, on Pricing, reproduced below.  They have a lot of interesting...

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The Virtues and Opportunities in Being #2

In our insular tech world, we’re all obsessed with being #1.  Look at Google Search vs. Bing + Yahoo!  Facebook vs. Google+.  Salesforce vs. nobody else of any scale.  Etc. etc.  We all know in tech,...

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Measure Your Churn. But What’s Even More Important is to Measure Your Almost...

Churn is a paramount topic in SaaS, as we all know.  If every dollar of ARR is worth $6+ in the long term, including upsells and second order revenue … then of course, by the same token, for every...

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Hyperaggresiveness … Can You Do It?

Recently I’ve met with several of my friends who are moving on, or have moved on, to their next SaaS company after some real success in their first one.  SaaS 3.0 entrepreneurs, I guess. They all have...

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Things Not to Share With VCs (and Others) Pre-Term Sheet

A version of this post was published on Forbes from a question originally on Quora.  I thought it would be worth expanding on here. ————- Most of us founders are naturally transparent, or at least,...

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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...

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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...

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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...

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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...

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Why You’ll Want to Raise $100,000,000 for Your SaaS Start-Up: The Incremental...

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...

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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...

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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...

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Our Eloqua vs. Marketo vs. Pardot Case Study, Take 2: The Marketo S-1/IPO,...

Several months back, we took advantage of ExactTarget’s $100m acquisition of Pardot (the arguable #3 player in the Marketing Automation space) to do an interesting case study of 3 paths taken in the...

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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...

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Hyperaggresiveness … Can You Do It?

Recently I’ve met with several of my friends who are moving on, or have moved on, to their next SaaS company after some real success in their first one.  SaaS 3.0 entrepreneurs, I guess. They all have...

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The SaaS Year of Hell. And Then – Reignition.

I was recently at an event with a SaaS-ish CEO who was, clearly, miserable.  His business was doing $30m+ and growing nicely.  He was about to introduce a new product that he thought could be...

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Great Free Tool from SalesLoft: Daily Job Change Alerts (via LinkedIn API)

Kyle Porter, CEO and co-founder of SalesLoft, recently did a great in-depth interview with SaaStr.  We’ll repost some of that and you can see it now here. While doing the interview, I had a chance to...

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If You Sell Your Company, Use a Banker

When I sold my first company, I used a banker, an M&A advisor.  When I sold my second, I did not.  Not using a banker the second time was a mistake. The benefits are nonobvious, somewhat...

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