How to Run a Department

In this post we'll run through a few of the factors that are unique to running a department, and how you should navigate them | Continue reading


@staysaasy.com | 1 year ago

How to Be a Senior Leader

If you want to get promoted as a manager, or are considering whether to promote someone on your team, check out our guide on how to be a senior leader at a fast-growing company. | Continue reading


@staysaasy.com | 1 year ago

Notes and Errata (From Previous Posts)

One of the joys of putting content out into the universe is the feedback we’ve gotten, both positive and critical. The latter, in particular, has been useful in refining our ideas. Herein lies some notes and errata - things we got wrong or not quite right. | Continue reading


@staysaasy.com | 1 year ago

Small Performance Cues

Over many years in industry, you start to see patterns that are suspiciously correlated with lower performance. Here are some small performance cues to look out for. | Continue reading


@staysaasy.com | 1 year ago

Good Managers Write Good

In my time observing managers, one observation seems to repeat again and again: good managers write well, and bad managers write poorly. In fact, the best managers I’ve ever had were not just good writers, they were terrific. And the worst managers I’ve ever had were not just bad … | Continue reading


@staysaasy.com | 1 year ago

Low Context – Software's Silent Killer

As companies grow, context can become a scarce resource. As more variables, people, teams, products, customers, and coworkers create an increasingly infinite combination of possible ways to move forward, deep context on what to do and how to do it should be thought of explicitly, … | Continue reading


@staysaasy.com | 1 year ago

Value Sell Recruiting

Articulate The Value Of What Candidates Care About | Continue reading


@staysaasy.com | 1 year ago

How to Improve Your Gross Margins

The challenge of how to increase the critical metric of gross margin is a multiple choice question, not free response. Here's how to do it. | Continue reading


@staysaasy.com | 1 year ago

Battlefield Product Management

Your lead PM just quit. These are the steps that absolutely cannot be skipped, and an approach to tackling them that can hopefully be executed by someone who is busy, distracted, or otherwise not a trained PM. | Continue reading


@staysaasy.com | 1 year ago

The Most Important Performance Management Rule for Software Engineers

Merge code every week. That’s what you should be saying to your new Software Engineer hire. Let’s discuss. | Continue reading


@staysaasy.com | 2 years ago

Ways to Expand Your SaaS Business

SaaS growth is a multiple choice question rather than a free-response essay. Learn the standard ways to grow your SaaS business here. | Continue reading


@staysaasy.com | 2 years ago

Working Across Departments

In any organization, working across departments comes with a lot of interesting challenges. Below, find a guide to navigating some common challenges in cross-departmental coordination. | Continue reading


@staysaasy.com | 2 years ago

Selling to the Enterprise: Be Enterprise-Ready

In this post we'll lay out some of the most important enterprise features to add to your product. The activities listed here will help you move up-market, as surely as brushing your teeth and having good hygeine will help you land a hot date. | Continue reading


@staysaasy.com | 2 years ago

Stop Writing Great Runbooks

Instead, fix your production issues. | Continue reading


@staysaasy.com | 2 years ago

The Swiss Army Product Management Team

If you want to be excellent at fielding a diverse array of business needs you must field a diverse team. Staffing a wide array of skills and experience makes it much more likely that your PM team will have a qualified person for any given need. | Continue reading


@staysaasy.com | 2 years ago

Working with Integrity

A person has got to have a code. | Continue reading


@staysaasy.com | 2 years ago

Debugging My Work Health

Many intangible attributes go into building a great company that are just as important as hard skills. Identifying and harnessing hard-to-measure skills allows you to capitalize on the most special traits on your team. | Continue reading


@staysaasy.com | 2 years ago

Managers Should Optimize Job Satisfaction, Not Happiness

Managers should be optimizing people’s job satisfaction, not their happiness. Trying to make a job facilitate happiness leads to perverse incentives and unattainable goals. It’s at best a distraction. At its worst it causes teams and companies to fall apart. | Continue reading


@staysaasy.com | 2 years ago

Behold the Power of Small Data

Your most important data is Small Data. Let’s learn how to use it. | Continue reading


@staysaasy.com | 2 years ago

Where to Innovate, Where to Imitate

Growing fast requires making decisions and executing fast. One of the quickest ways to make and follow through on important choices is to figure out the areas of your business where you can imitate industry best practices, and where you'll need to innovate. | Continue reading


@staysaasy.com | 2 years ago

A Special Source of Product Managers: Transfers from Customer Success

If you want to scale a product team quickly, one of the best ways to move fast is to convert talent from other vocations. One of my favorite sources for SaaS product managers is your own post-sales team – particularly recruiting PMs from customer success. | Continue reading


@staysaasy.com | 2 years ago

Give People Something to Look At

Giving people something to look at can be the difference between an awkward chat and an amazing conversation. | Continue reading


@staysaasy.com | 2 years ago

Stop Looking for Mentors

You can look for mentors, but that ain't fun - so just think of a question to ask someone. | Continue reading


@staysaasy.com | 2 years ago

Managing Engineering Managers: A Primer

A primer on managing engineering managers. | Continue reading


@staysaasy.com | 2 years ago

Selling to the Enterprise: Crafting Product Narratives

As a product leader, you can accelerate your company's sales growth by steering development in ways that reinforce the central narrative of your product. There are four common narratives that drive a buyer's decision to open up their wallet. Let's go through each, explain what th … | Continue reading


@staysaasy.com | 2 years ago

Simple Ways to Be Less Divisive

A guide to scaling product & engineering teams from $0 to past $100M ARR | Continue reading


@staysaasy.com | 2 years ago

What to Do When Your Team Quits

You might find yourself - especially with the resignation in all the news - with a bunch of team members that leave all at once. Here’s some things you can do about it. | Continue reading


@staysaasy.com | 2 years ago

Leaders Whose Time Has Passed

Tech has a standard set of leadership profiles that are discussed regularly. However, that set is missing a number of common personas, whose time is limited. | Continue reading


@staysaasy.com | 2 years ago

Goals, Problems, Solutions

Here's a quick playbook that I use whenever I'm pulled into a situation, particularly to resolve a misalignment | Continue reading


@staysaasy.com | 2 years ago

Things 10x People Do

10x people exist. There are people that have 10 times the productivity and impact of their peers. | Continue reading


@staysaasy.com | 2 years ago

Beware the Beloved Leader of Malcontents

One organizational wart that can occur is an unhappy team that loves their manager. Let’s explore how this situation arises and how to fix it. | Continue reading


@staysaasy.com | 3 years ago

On Writing Performance Reviews

A guide to scaling product & engineering teams from $0 to past $100M ARR | Continue reading


@staysaasy.com | 3 years ago

Three Types of Management Problems

A guide to scaling product & engineering teams from $0 to past $100M ARR | Continue reading


@staysaasy.com | 3 years ago

Competitive Analysis for Product Engineers

In my experience, most professional software engineers in industry have little to no experience doing competitive analysis. That’s a shame, because competitive analysis is one of the most useful skills that an engineer can have. | Continue reading


@staysaasy.com | 3 years ago

I Read Product Manager Resumes

These are the two most important traits for evaluating product manager resumes. | Continue reading


@staysaasy.com | 3 years ago

Low Priority Issues and Time

Small issues become big ones. | Continue reading


@staysaasy.com | 3 years ago

Machine Learning Won't Save Your Startup

Using machine learning to differentiate your product is like driving a fancy sports car to stand out when picking someone up for a date. | Continue reading


@staysaasy.com | 3 years ago

Avoiding the One Step Back

Teams, especially at growth companies, often have a pattern of taking two steps forward and one step back. Let’s explore how teams often unknowingly slip after growing and try to prevent it. Only forward steps! | Continue reading


@staysaasy.com | 3 years ago

Data: Use, with Caution

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@staysaasy.com | 3 years ago

Unlimited Is a Ponzi Scheme

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@staysaasy.com | 3 years ago

Maximizing the Value of Reference Calls

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@staysaasy.com | 3 years ago

A Blessing and a Curse

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@staysaasy.com | 3 years ago

Unforced Management Errors

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@staysaasy.com | 3 years ago

Management Scrutiny

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@staysaasy.com | 3 years ago

7 Reasons Your Growth Startup Is Hiring Too Junior

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@staysaasy.com | 3 years ago

Soft Skills for Managers

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@staysaasy.com | 3 years ago

Selling to the Enterprise: Avoid Saying No

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@staysaasy.com | 3 years ago

The First Two Weeks in a New Role

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@staysaasy.com | 3 years ago