[I originally shared this post on Medium, but I've since moved here.]
I'm a big fan of Jacob Bennet's "The 5 paid subscriptions I actually use in 20XX as a Staff Software Engineer" annual series, and I was inspired to share my own take from the perspective of a first-line engineering manager.
The total cost is $86 per month, easily justified if they save me just 40 minutes of work time. Rokt covers all but Willow Voice and Ulysses, both of which I pay for personally.
Given how quickly the latest and greatest tools are changing, though, I expect to have a different stack by next season.
Cursor ($20/mo)
I miss coding. Since transitioning from IC to manager, I rarely have the time to go deep in the tech stack or ship features hands-on. I don't need to, but I like to.
I'll admit I was a Cursor hater basically until about a month ago. I found it clunky, introduced inexplicable bugs, and often made my life harder. I am simply not smarter than AI, and debugging vibecoded hallucinations became a nightmare.
That said, I finally got Cursor to work for me: continually screaming to use test-driven development, writing aggressive Cursor rules, and tightly scoping chats to single, atomic tasks. It's materially helped me to actually get back into the code base and ship some features, even if they're small.
My favorite instruction (source: u/Worst_Artist)
I find it most useful for relatively simple tasks that one of my engineers could probably knock out in a couple of hours, but the biggest benefit I found from Cursor is that it allows me to take on these small, potentially-distracting tasks that let my engineers focus on meatier designs or more cognitively-demanding problems that require days of deep, dedicated focus.
A few of my favorite cursor links:
- Cursor Rules docs — specifically a heavy user of the
/Generate Cursor rulescommand. - Off-the-shelf rules from cursor.directory.
- PatrickJS/awesome-cursorrules (use with caution: some are much better than others.)
Link: https://cursor.com/
Willow Voice ($15/mo)
Dictation lowers the activation energy for the tasks I least want to do. For me, that's writing interview reviews.
After an hour-long interview, writing a thoughtful review can feel like a slog. With Willow Voice, I just speak. It doesn't have to be perfect. The value is in reducing friction.
A few other areas of use:
- Responding to emails and chats.
- More conversational discussion with LLMs.
- Getting first drafts of documents down quickly.
- Overcoming writer's block.
- Practicing saying what I mean.
Referral Link: https://willowvoice.com/?ref=CBARKER92 (You get a free month; I get a free month 🤝)
The Willow dashboard from my personal account.
ChatGPT ($20/mo)
I use ChatGPT for everything and all the time. It hasn't automated my day-to-day responsibilities, but it has dramatically reduced the amount of time some of them take and has freed up my bandwidth to focus on more interesting problems (like taking on small coding tasks with Cursor).
I philosophically view ChatGPT as an enhancement tool rather than a replacement tool, and with that framing, I find myself to be less disappointed when it doesn't do exactly what I want.
Not directly related to work, ChatGPT will also do heavy, hard-hitting research on my behalf so I don't lose the plot of my actual job.
"Militaristic Desire and Latent Aggression: The Rise of Nu Metal and Butt Rock in 1990s American Culture," or the PhD dissertation that never was.
Link: https://chatgpt.com/
Brief Interlude on Gemini:
We get access to Gemini through Google Workspace, and I think it's fine. If I could only have one right now, I would pick ChatGPT over Gemini because I prefer ChatGPT's web search features.
Granola.ai ($18/mo)
Meetings can be dense, fast-moving, and poorly documented. Granola.ai is my go-to automated note-taking app.
The transcription quality is solid, and I regularly drop raw transcripts into ChatGPT or Gemini to chunk content and generate structured meeting notes outside of what's provided in-app.
How I use it:
- Track decisions and action items
- Remember who said what
- Verify dates and commitments
Link: https://www.granola.ai/
Ulysses ($6/mo)
Ulysses is designed for content writers, not engineers, but I like the distraction-free writing experience and Markdown support outside of a browser.
One underrated feature: with some tinkering, it works with Google Drive as a backend. That means I can draft everything — architecture designs, policy docs, team strategies — in Ulysses and then seamlessly shift to Google Docs for collaboration.
The first draft of this post as viewed in Ulysses.
Link: https://ulysses.app/
Excalidraw ($7/mo)
Some tools just stick. Excalidraw is still my favorite for diagramming, even after trying to switch to more specialized alternatives. I have yet to find anything else as fast or fluid.
Bonus: it's also great for last-minute D&D maps.