Stickiness. There perhaps isn’t a more precious gem to the SaaS business model than the concept of Stickiness.

The SaaS business model is a recurring business model. It is only successful if users continue to pay month-after-month, year-over-year. This means that any product delivered as a SaaS product must deliver recurring value. The value needs to match the model. In short, a SaaS product needs to be sticky.

This post will introduce a product philosophy that is essential for driving maximum stickiness for a product. And I call it the “All My Shit’s In There” Factor.


Yeah, I know. Bear with me. This was a product lesson I learned years ago while building one of my first SaaS businesses. And like all good life lessons, I learned this one the hard way. …

Good product data is an essential part of any modern software company’s operation. It ain’t just for product analytics anymore. Marketing needs it to effectively target prospects and users. Sales needs it to understand which trial accounts are worthy of attention. Customer success needs it to help them identify issues and opportunities. Operations needs it to help support forecasting. This data is the lifeblood of software business.

But one of the biggest challenges with regard to this data (beyond getting the product/engineering team actually track the data) is communicating what is being tracked — and what it is all called — to the teams that need it. …

I recently had a conversation with a top CS leader who was struggling to build and get their “Playbooks” to work.

My suggestion was — forget it. Playbooks suck. She was surprised at my take on this as the idea of Playbooks has been a pretty standard part of the Customer Success function for a long time. And I understand why.

Playbooks — when used in the context of a Sales or CS team — represent lists of “plays” (or actions) that a rep is required to apply against any new lead or customer. They are borne from the belief (hope?) …

I’m writing this post as a follow-up to David Apple’s great post — Nobody knows the ROI of their CSMs. Anyone in charge of building a CS department/team should read it (and follow David, in general).

I love that David confronted the misguided practice of trying to assign an ROI to a Customer Success Manager head-on. He clearly explains why this is a fruitless exercise and one that we need to just stop.

David is spot on when he opens his argument by asking,

What’s the ROI of your Mom?

Haha. Good line (and sounds like the beginning of an odd “Your Mama” joke). …

For a while now, we in the SaaS world have been talking about our “stacks” — most commonly our “Marketing” or our “Sales stack”.

My personal favorite kind of stack

For some, this may sound like obnoxious Silicon Valley buzzword-play, but a stack is nothing but a collection of software tools we use to execute a set of jobs in a specific function.

A Marketing stack = set of software tools used to run the marketing function.

But what we haven’t started talking about is a stack to cover what is arguably the most important function for a SaaS business: product engagement. …

If you are reading this, I’m assuming that you are doing a good job tracking your product usage data. How users are interacting with your product, what features they’re using, when they are using them, and how often. All that stuff.

I think at this point, most of us are doing a good job at this. We’re generating piles of data on our users’ activities every day.

Level 1.

From here, many of us are using some kind of general analytics tool, some query interface, to allow us to pull up and visualize this data in different ways.

Level 2.

Some of us are even taking things to the next level and making this data available to other teams in order to help them make decisions and drive specific actions. Some of us are using

As a young entrepreneur, one common piece of advice you hear is to “build a product that solves a problem you have yourself.” Scratch your own itch, they tell you.

And that advice is logical and pretty well reasoned. If you are solving a problem you have yourself, then you will be intimately familiar with the nuances of that problem and should be able to create a great solution. If it’s your own pain, you’ll attack it with passion and perseverance.

Totally makes sense.

Up until now, however, I’ve opted for the alternative approach. Not to solve a problem for myself, but to try to identify a problem that a lot of people/companies have. …

Since this race has started, friends and family have asked me why I will be voting for Bernie Sanders. So…I decided to lay out my reasons in a super long blog post that no one will read. Soooo…here goes:

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I have been a huge fan of Bernie Sanders for ~10–15 years now. As a New Englander, I first heard of this spitfire, independent Senator from Vermont from some local coverage. …

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It’s easy to build walls. Any average, unskilled person can build a wall. All that is required is stacking objects on top of each other, in a row, as high as desired. The objects could be anything — stones, bricks, chain links, Rubix cubes — anything. Simply start stacking and voila — a wall. Very simple.

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Bridges, on the other hand, are not easy. They require specific, high-level skill sets — geometry, physics, design, geology, construction, and more. They require planning, scouting, favorable conditions, and strong collaboration. The slightest miscalculation can lead to failure — injury…death. …

As the famous Apple Think Different campaign said:

“Here’s to the crazy ones. The misfits. The rebels. The troublemakers. The round pegs in a square hole. The ones who see things differently.”

I’d like to add to this list — The Unemployable Ones.

This post was triggered by the inevitable breakup between ESPN and Bill Simmons — which has created quite the stir:

For anyone who followed Bill since his days as a lonely (and amazing) Boston sports blogger, it was very clear to see that Bill was different. He had a new voice — a different perspective and a style unlike anything else that was being produced by the mainstream sports media of the time. …


Derek Skaletsky

Tech founder (mostly SaaS). Latest — Sherlock (; Boston expat; Hollywood escapee; hack photographer; dad (x2)

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