One of the most consistent observations I've had in my time in startups, scale-ups, and public companies is that smart people with context on a tricky situation almost always know exactly what they need to do.| Stay SaaSy
A guide to scaling product & engineering teams from $0 to past $100M ARR| Stay SaaSy
A guide to scaling product & engineering teams from $0 to past $100M ARR| Stay SaaSy
A guide to scaling product & engineering teams from $0 to past $100M ARR| Stay SaaSy
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, because its thoughtful allocation can make, or, notably, break, a company’s productivity.| Stay SaaSy
As people become managers, it's quite common for their team members to want to commiserate with them. This is especially true for friendly, competent, reasonable-seeming managers – people want to commiserate with winners. But commiseration, especially with your direct reports, is organizational poison.| Stay SaaSy
Know where AI is a crutch and where it's an abstraction.| Stay SaaSy
Companies are just groups of people with money on the line, and they need rules to avoid descending into chaos. Startups are born without any rules, so as you scale someone ultimately needs to set up everything from scratch. As a result, setting policies is one of the most important roles that one plays as an executive.| Stay SaaSy
Words matter.| Stay SaaSy
Reason from first principles to establish what your problems actually are, but reason from analogy to figure out what to do| Stay SaaSy
A collection of practical advice.| Stay SaaSy
Accountability is the only way that anything gets done at scale. Here are some ways that smart people screw up accountability on their teams, often despite the best of intentions – and what to do about them.| Stay SaaSy
It was a very good year.| Stay SaaSy
When figuring out what to do, start with the problem.| Stay SaaSy
These are the heuristics that I use for professional networking. I think I'm a pretty good networker, but not any sort of natural networking savant – I've just been able to find good results by following a few easy habits. Networking is kind of like working out. It's easy to get started, and a relatively small amount of effort gives you significant benefits. If you follow some incredibly basic rules and aren't lazy, you too can build a great network.| Stay SaaSy
One of the best ways to build executive presence is for other executives to obviously care about what you have to say. This time, we're going to dive into the behaviors that earn respect from other executives – the traits that help make them allies, and that prevent them from resenting you or taking you for granted| Stay SaaSy
Changing behavior once you’ve given notice always makes you look bad.| Stay SaaSy
To set an effective strategy, you need to orient yourself in regards to your company's strategic landscape – where the opportunities lie, where there are gotchas in your market, how the dynamics are likely to evolve. Here are the questions that I try to make sure I'm always able to answer before setting SaaS product or business strategy.| Stay SaaSy
Don't do it!| Stay SaaSy
A guide to scaling product & engineering teams from $0 to past $100M ARR| Stay SaaSy
Fights between a manager and report can be some of the most stressful experiences in life.| Stay SaaSy
When it comes to career growth, managers and companies often make the mistake of trying to focus on everyone, all at the same time.| Stay SaaSy
Best practices for building a company are passed from person to person like ancient tribal knowledge of which plants in the forest are edible. Here's a list of best practices that should be more universally understood.| Stay SaaSy
The first rule of managing high performers is that you must manage them.| Stay SaaSy
Supporting multiple platforms can be a repetitive and boring problem, or a fun challenge.| Stay SaaSy
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.| Stay SaaSy
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.| Stay SaaSy
Small issues become big ones.| Stay SaaSy
Have one main focus and keep it that way.| Stay SaaSy
My personal favorite reading materials that have helped me think about leadership, management, and technology.| Stay SaaSy
One of the most important core product management skills is the ability to triage unsuccessful products and avoid spending unnecessary effort on products that are destined to be losers.| Stay SaaSy
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.| Stay SaaSy
A guide to scaling product & engineering teams from $0 to past $100M ARR| Stay SaaSy
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.| Stay SaaSy
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.| Stay SaaSy
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.| Stay SaaSy
A guide to scaling product & engineering teams from $0 to past $100M ARR| Stay SaaSy
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 writers, they were uncommonly shoddy.| Stay SaaSy
Opportunities within companies are all inherently different. Here's how to make a fair system with this reality.| Stay SaaSy
Your most important data is Small Data. Let’s learn how to use it.| Stay SaaSy
One of the most common management mistakes is not providing clarity when people are wrong on important, invested efforts.| Stay SaaSy
“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.| Stay SaaSy
It's been a weird and wild week in social media land. Let's talk about what we can learn from the rivalry turned backyard bare knuckle boxing match that is Twitter vs. Facebook Threads| Stay SaaSy
When you start a new role on a software team, you should immediately immerse yourself in the tooling and data on how things fail.| Stay SaaSy
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.| Stay SaaSy
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.| Stay SaaSy
A guide to scaling product & engineering teams from $0 to past $100M ARR| Stay SaaSy
The remote discussion is complex and hard to discuss rationally. In this post we discuss the future of remote work, and provide a framework for thinking through the remote revolution| Stay SaaSy
It's been a weird and wild week in social media land. Let's talk about what we can learn from the rivalry turned backyard bare knuckle boxing match that is Twitter vs. Facebook Threads| Stay SaaSy
Achieving your goals, in its most basic form, can be a very simple process.| Stay SaaSy
Executive presence describes a set of behaviors that will influence others to fully listen to what you say. You can be right all the time, and the hardest worker at the company, but to be maximally effective people need to judge your ideas on their own merits.| Stay SaaSy
Larger companies move slower because they accumulate red tape as they grow. Bureaucracy doesn't fix itself – the people that you task with building processes don't wake up one day, realize that they've unintentionally harmed the company by adding overhead, and quit. Here are a few signs of bureaucratic practices, the sometimes surprising ways to identify them, and what to do to resolve them.| Stay SaaSy
Explicit DEI focus has been one of the biggest changes to modern management responsibilities. This is a good thing - done right, DEI makes a business the best version of itself. However, done wrong, attempts at DEI can be confusing, distracting, and downright problematic.| Stay SaaSy
You see it everywhere: Engineers complaining about the product managers that they work with. Hating on PMs is so universal that it's always good for a light chuckle in the right circles. This cycle is worth breaking.| Stay SaaSy
Learning how to manage is a long race - it takes many years and each lap offers new learnings. Along the way, anchors emerge that can help orient a manager when a number of other variables are in flux. Below we offer a number of these anchors. They are based on philosophy, experience, and analysis; we hope they’ll be of some use.| Stay SaaSy
A Culture Virus is a contagious idea that hooks into your culture like a pathogen, passing from person to person, and very often preying on the weak and struggling - the people who are susceptible to convenient excuses..| Stay SaaSy
Getting acquired is like meeting the world's worst in-laws: Judgmental, money-obsessed, potentially driven by ego reasons that are impossible to fully divine. In this post we run through a range of questions that acquirers typically ask when deciding to buy a company, going beyond the surface analysis of whether the companies have obvious synergies.| Stay SaaSy
Teams naturally start to incur management debt as they grow and become more complex, just as codebases incur tech debt. The combined weight of past decisions creates a web of precedents and exceptions that can cause problems of varying size over time. Here are a few of the main types of management debt that we've seen, as well as some thoughts on how severe they are and how to unwind them.| Stay SaaSy
It's been a wild week in Twitter land, as Elon has grabbed the controls of the plane not with the detached cool of Han Solo, but something more like the wild-eyed, manic smile of Cyrus the Virus in Con Air. We're here to offer some thoughts on why some of what Elon is doing might make sense – and also why some of his moves really are as crazy as they look.| Stay SaaSy
The Dirty Work Theory: The lamentable work that many people avoid are great places to look for high impact, low hanging fruit.| Stay SaaSy
