Stay SaaSy

A guide to scaling product & engineering teams from $0 to past $100M ARR.
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2024: A SaaSy Year In Review
29 Dec 2024 | original ↗

It was a very good year.

Problem Driven Development
17 Dec 2024 | original ↗

When figuring out what to do, start with the problem.

Networking For People Who Don’t Network
11 Dec 2024 | original ↗

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...

A Practical Guide to Executive Presence: Earning Respect
19 Nov 2024 | original ↗

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

Don’t Act Differently After You Give Notice
10 Nov 2024 | original ↗

Changing behavior once you’ve given notice always makes you look bad.

Questions for Orienting Your SaaS Strategy
3 Nov 2024 | original ↗

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.

Stop Trying To Replace Your SaaS Products With AI
15 Sept 2024 | original ↗

Don't do it!

Harvesting, Fishing, Panning for Gold
18 Aug 2024 | original ↗

Here's a framework for how I think about bucketing challenges into different categories, each with its own approach for solving them: Harvesting, fishing, and panning for gold.

Standardizing
6 Aug 2024 | original ↗

Standardizing things feels productive, like cleaning up a messy room, and is a go-to move for leaders when they don't know exactly what to do next.

Fighting With Your Boss
15 Jul 2024 | original ↗

Fights between a manager and report can be some of the most stressful experiences in life.

I Like Dumb Plans
7 Jul 2024 | original ↗

I've seen a lot of startup growth, and I like dumb plans

Don’t Try To Step-Function Everyone All At Once
12 Jun 2024 | original ↗

When it comes to career growth, managers and companies often make the mistake of trying to focus on everyone, all at the same time.

Unspoken Startup Folk Wisdom
21 May 2024 | original ↗

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.

Managing High Performers
8 May 2024 | original ↗

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

Platform Support
17 Apr 2024 | original ↗

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

Consistent Traits of the Best Startup Scalers
11 Apr 2024 | original ↗

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
4 Apr 2024 | original ↗

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
24 Mar 2024 | original ↗

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
12 Mar 2024 | original ↗

Have one main focus and keep it that way.

A Technology Leader’s Non-Technical Reading List
4 Mar 2024 | original ↗

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

Engineers Are Not A Commodity
17 Feb 2024 | original ↗

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
11 Feb 2024 | original ↗

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
23 Jan 2024 | original ↗

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
7 Jan 2024 | original ↗

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
2 Jan 2024 | original ↗

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
18 Dec 2023 | original ↗

Reflections on a very SaaSy year.

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