2023: A SaaSy Year In Review

Happy Holidays Stay SaaSy community!

What a year it’s been: AI started eating the world, crypto and banks felt the heat, and the software ecosystem was a mixed bag - some winners kept winning, there were more layoffs, lots of hope, but also lots of continued belt tightening.

Through it all, we had a lot of fun posting ideas, getting feedback, and engaging with the Stay SaaSy community.

This is the 2023 Stay SaaSy year in review.

A Year In Numbers

Some high level numbers and milestones for the year:

  • We published 30 posts this year
  • We moved to Substack
  • ~92k people visited staysaasy.com
  • We launched a Guides page to help new readers find content that they might find helpful
  • Our subscriber count doubled

Our most popular posts of the year were sometimes a surprise to us, and sometimes more expected. Either way it’s always great to see something resonate.

Numbers To Know For Managing (Software Teams)

Our first popular post of the year was about numbers to manage software teams by. This post started as a question from the SaaSy engineering manager to the SaaSy product manager: “What do you think about one of these Buzzfeed style number posts?”

This was an experimental format, but it resonated with a lot of people. Management is often a very hard-to-define task, and engineering managers especially seek refuge in numbers. Hard-earned anchors that can act as guideposts in an otherwise ambiguous journey can be very useful.

A Practical Guide To Executive Presence

This post was written by the SaaSy PM, and was inspired by observing how different various individuals’ career trajectories could be based upon their executive presence. What initially started out as a single thought (“Don’t show up to work dressed like a ski lift operator, unless you’re actually a ski lift operator) became a broader set of observations on the behaviors that give companies the confidence to put you In Charge (™).

The popularity of this post led the SaaSy engineering manager to start wearing different shoes to work after reading this post – remember to never be in both the youngest and shabbiest 1/3 of your company!

The Future of Remote Work

This post on the market and workplace dynamics driving remote work got a fair amount of popularity and some really thoughtful commentary. The central concept seemed to resonate: That remote work discourse gets it all wrong because people can’t emotionally separate the concept that remote teams have issues, from the concept that remote hiring often opens up a stronger workforce.

Your Small Imprecise Ask Is a Big Waste of Their Time

The popularity of this post made sense in retrospect - one thing we’ve learned through previous posts is that pithy advocacy for avoiding bad management behavior strikes a chord. One of our most popular posts of all time had a similar theme - Don’t Joke About Firing People.

Posts like this often find lots of people commiserating about being on the receiving end of the behavior we’re saying to avoid. If there’s one takeaway from the continued popularity of these articles it’s that manager behavior can have asymmetric downsides to employee morale, and while managers shouldn’t feel it’s their job to make their team happy, it is their job to not make the team frustrated (which is harder than it may seem).

Practical Ways To Increase Product Velocity

The authors of Stay SaaSy have been fortunate enough to invest in and advise a few companies. In our conversations with these teams, we’ve found that a very high percentage of discussions essentially boil down to “how do you think we could build products faster?” We went back and forth several times about whether this


Posts we thought would be more popular

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

Listen, I screwed up. I posted this article on the Sunday after Black Friday when everyone’s inbox was filled with deal emails. Not only did this post not get traction, it led to a spike in unsubscribes as people had their “no more email” fingers on the trigger.

That said, I was really bummed that this post didn’t start a conversation. The core idea – that disparate symptoms can have one root cause – is one of the more challenging management problems to solve. I’m reflecting on how to better articulate this idea in the future.

PM: How Acquirers See Your Company

People in tech are obsessed by liquidity events, and this was our first foray into pulling back the veil on how to actually get acquired (or acquire someone else). The questions laid out in this post really will lie between you and a profitable exit, and much of the advice that I’ve seen on the internet appears to come from people who haven’t actually seen what intensive M&A due-diligence looks like.

If you’re running a startup, check this post out – my goal was to help somebody out there make some money!

PM: Startup Make-Believe

I was surprised that this post on how startups unwisely mimic larger, more successful companies didn’t resonate more. I see this happen all the time – startups try to copy a bunch of “best practices” from Google and end up shooting themselves in the foot (if not the face). Having indulged in my fair share of startup make-believe, this was my best attempt to save people months of time that they’ll never get back.

Post we thought wouldn’t be as popular

EM: Numbers To Know For Managing (Software Teams)

Not only was this post experimental, but it made some bold claims about a lot of different numerical values. I figured we’d get some more debate and criticism on numbers that clearly advocated; I was really surprised that there wasn’t much by way of opposing thoughts.

Posts people liked the least

EM: DEI For Dummies

It was likely predictable that people were going to spew vitriol over a post about DEI. I was surprised at how diverse the vitriol was: comments on this article claimed I was liberal scum, conservative scum, and everything in between. And all of that for saying you should pay people fairly, leverage your team effectively, and get some variety of backgrounds on the team.

Short Stories: The Tweets

We had a lot of fun tweeting this year. You can see our highlights here. It’s worth mentioning that we both post from the same account with 0 coordination, and as a result typically don’t know what the other is going to say.

Our most popular tweet of the year (and all time) was:

EM: My favorite Tweet from the year by the SaaSy PM was:

That tweet sent me spiraling a bit about how I’ve made choices in life. Luckily I had a good episode of The Deadliest Catch queued up and the crab count pulled me out of existential despair. In any case, I found the Tweet to be a really interesting and useful observation.

PM: This tweet by the SaaSy engineering manager really struck a chord with me, as I’ve noticed recently that a strangely high percentage of my strongest team members seem to share a relatively mild but clearly suboptimal pattern of behavior. This post helped me to acknowledge what I think I always knew deep down – I’m probably the root cause of the issue in some way that I don’t yet understand. I’m still reflecting on where to go from here but I have a renewed sense of purpose about it.


We really enjoyed all the feedback from the community this year. We answered a number of emails, including interesting and in-depth conversations about management issues. Reminder you can find us at hellostaysaasy@gmail.com.

Synopsis and Thank You

Well friends, that concludes the year in review for team Stay SaaSy. We want to thank you again for all the feedback, engagement, and encouragement. We hope you have a great end of 2023 and an amazing start to 2024.

One final note – we did get a good amount of questions about who we are this year. We continue to post anonymously because it gives us the latitude to write freely and frequently, and to let our ideas live on their own merits. That said, we’ll offer some clues to our dear readers about our identities. If you think you know who we are, shoot us an email and maybe we’ll buy you a soda. If you don’t, look out for more clues in the future.

The first and most important fact that we’ll address: We occasionally get questions that essentially boil down to whether we actually know what we’re talking about. Are we running teams at a Series A startup with $17.99 in ARR? Are we just 3 interns in a trenchcoat using ChatGPT?

All outcomes are relative, but suffice it to say that everything in Stay SaaSy is based upon real experiences that led to venture scale outcomes.

Here are some other clues as to who we are. We hope they’ll help humanize our account and make it feel less like you’re engaging with a GPT:

  • Stay SaaSy has two authors. One of us runs engineering (the SaaSy EM) and the other runs product (the SaaSy PM)
  • We work in enterprise SaaS but have experience at some of the biggest companies in tech, as well as ones you’ve never heard of, and some in between
  • We’ve seen the journey from $0 to $100s of millions of revenue
  • We have both lived in more than one of the major tech hubs in the USA