About Stay SaaSy

We started this blog to share what we’ve learned on how to scale product and engineering through all stages of startup hypergrowth.

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Managing High Performers

1970-01-01 08:00:00

The first rule of managing high performers is that you must manage them.

Platform Support

1970-01-01 08:00:00

Supporting multiple platforms can be a repetitive and boring problem, or a fun challenge.

Consistent Traits of the Best Startup Scalers

1970-01-01 08:00:00

Scaling up a startup – rapidly growing from say $2M to $200M ARR – is an exciting and challenging journey. From what I've seen, there are a few traits that disproportionately lead to startup scaling success.

Have Concerns And Commit

1970-01-01 08:00:00

The topic of how to communicate top-down decisions that you disagree with is an important one. It’s important because it is universal, it’s bad if you get it wrong, and it often means the kind of mature process that differentiates good and bad leaders.

Advice That I Can’t Get Out of My Head

1970-01-01 08:00:00

Across all of the reading I've done over the years, I've come across a few pieces of advice that I haven't been able to get out of my head. These slices of wisdom have been immensely helpful to me and I wanted to share them both so that others can benefit.

Getting Things Done In A Chaotic Environment

1970-01-01 08:00:00

Have one main focus and keep it that way.

A Technology Leader’s Non-Technical Reading List

1970-01-01 08:00:00

My personal favorite reading materials that have helped me think about leadership, management, and technology.

Engineers Are Not A Commodity

1970-01-01 08:00:00

Hiring big-company experienced executives to your startup is hard but important. Here are our thoughts on why it's challenging, what to look for, what to watch out for, and what actions to take.

Hiring Experienced Executives At Your Startup

1970-01-01 08:00:00

Hiring big-company experienced executives to your startup is hard but important. Here are our thoughts on why it's challenging, what to look for, what to watch out for, and what actions to take.

How To Fix Broken Teams

1970-01-01 08:00:00

Most teams break in very similar ways. And, even more luckily, most teams can be fixed in similar ways. So, let’s talk about diagnosing and fixing the most broken of teams.

Performance Reviews Matter

1970-01-01 08:00:00

Performance reviews matter a lot. In this post we’ll aim to explain why they matter, and give options to trim down your process.

This Is the Person Selling Your Product

1970-01-01 08:00:00

I had many negative misconceptions about sales teams before working in SaaS. After years as an engineer and product manager, high-skills sales reps are one of the groups whom I respect the most. This is what I wish that someone had told me about sales before I began working in tech – an introduction to the person selling your product.

2023: A SaaSy Year In Review

1970-01-01 08:00:00

Reflections on a very SaaSy year.

Practical Ways To Increase Product Velocity

1970-01-01 08:00:00

Speed determines victory for technology companies. Since the internet was invented, the fast have killed the slow. And out of all the ways that speed matters, product velocity – the pace at which you evolve your product – matters most of all. This post contains my go-to steps for debugging slow product velocity, particularly in SaaS.

Hidden in Plain Sight: Unraveling Big Problems Disguised as Small Unrelated Issues

1970-01-01 08:00:00

Pressure on complex systems can create many small, seemingly un-correlated issues that on the surface seem unrelated to their shared root cause.

Weak Power Gets Tested

1970-01-01 08:00:00

One of the most problematic setups in any organization is the installation of managers with weak power: Individuals who are given the responsibilities of management but who actually cannot wield them, because their power is weak and in name only.

Your Small Imprecise Ask Is a Big Waste of Their Time

1970-01-01 08:00:00

When managers and leaders don't specify the expected time investment of an ask, the time that is invested is almost never what was intended.

Startup Make-Believe

1970-01-01 08:00:00

Just like young kids, young companies love to play Startup Make-Believe: Pretending to be something that they're not, in particular a much larger and more mature business. Don't fake it if you haven't made it. Let's dive into the common temptations of Startup Make-Believe, why they exist, and why they don't make sense for an early stage business.

Thoughts on Product-Market Fit

1970-01-01 08:00:00

In the most simplistic view, there are only two phases in the history of a startup's life: Before product-market fit, and after product-market fit (PMF). The transition between the two is intense and fundamentally reshapes the experience of working at a startup. Let's dive into what product-market fit is and isn't, and what to do when you've found it.

Fair but Unequal

1970-01-01 08:00:00

Opportunities within companies are all inherently different. Here's how to make a fair system with this reality.

(People on) Nice Teams Finish Last

1970-01-01 08:00:00

One of the most common management mistakes is not providing clarity when people are wrong on important, invested efforts.

Dont Bring Me Problems, Bring Me Solutions

1970-01-01 08:00:00

"Don't bring me problems, bring me solutions" is a common message that one imagines a stereotypical CEO saying to their teams. While this literal phrase isn't particularly common in the wild, it's rooted in some deep underlying truths about communication with executives. In this post, we'll dissect this catchphrase as a means of analyzing how to effectively communicate upwards, whether to a senior manager, executive, or CEO.

New Hires: Learn How The System Breaks

1970-01-01 08:00:00

When you start a new role on a software team, you should immediately immerse yourself in the tooling and data on how things fail.

When To Hire Your First PM

1970-01-01 08:00:00

Many companies find it tempting to hire a first PM too early. In this post we'll discuss when to hire your first PM, when not to hire your first PM, and what to consider doing instead.

Moving From IC to Engineering Manager

1970-01-01 08:00:00

Moving from individual contributor (IC) to engineering manager is a big move in many careers. These promotions and the mechanics of the change are done very differently across industry, with varying results.