Ship Happens, Week 11
A career change for yours truly, what I learned from this job search, and breakthroughs managing stress with my Oura Ring.
Happy Friday everyone! Welcome back to Ship Happens, your weekly product manager newsletter.
I'm using this newsletter to share at least three things l've come across this week to help you build better product. Subscribe so you don't miss these when they come out:
One announcement: there will be no newsletter next week. Taking the kids to Florida 🐊 for spring break. Wish us luck!
On to this week's thoughts and updates:
1. Goodbye Udemy, hello AI Copilot at Procore!
I mentioned last week that an end of an era was nigh for me, and so it has come to pass that I am leaving Udemy on Monday after almost 4 years at the company. (Would have been 4 years officially in April. Missed it by a hair!)
I’m so grateful to have worked with so many bright folks in Austin and the Bay Area on many growth, conversion and experience challenges at Udemy. I got to reunite with many people I loved working with at Vrbo! We IPO’d, my younger son was born during that time also, many adventures were had. Thank you to everyone I got a chance to work with. Udemy will always have a special place in my heart. 💜
I’m super excited to be joining the team at Procore in April! I’ll be working on their AI Copilot experience, leveraging a lot of what I’ve learned here and building my own stuff like this resume reviewer for product managers:
It’s a really exciting chance to work on something different from growth & conversion, and of course in LLMs and AI, an area I’m super passionate about as y’all can see from my musings here. Off to new adventures!
As such, I’ve been learning and re-learning some important things about the job search over the last 30 days or so. So I thought it’d be good to share those learnings below for you in case you’re facing a job search, either now or down the road.
Below are some thoughts about the process of changing jobs and what I’ve learned about it over the last 15 years that you can apply for yourself.
2. Don’t bother applying online. Get a referral.
Another hiring manager and I were comparing notes about what he was seeing as part of the recruiting process for an open role he had.
He said that when he opened the role, he had over 400 applicants in a little over 24 hours. But in reality, 5-10 of those applicants were actually qualified with good resumes. The rest probably were either Easy Applies or AI bots submitting on behalf of candidates with AI generated resumes.
When you apply online, just remember you’re competing with of course AI-submitted candidates, but also in general nameless, faceless people. Trust between you and the company, recruiter and hiring manager will start low. You’ll have to build it brick by brick as a candidate, which leaves very little room for error.
When you have the all-powerful referral, especially if it’s a really quality one from your network of people you’ve actually worked with or at least know you really well, you have a big leg up over the faceless AI-generated masses.
This makes a strong case for referrals in your job search, but just to add a kicker and bring this home, I asked Perplexity about how best to look for jobs. It told me that 80% of jobs get filled via referrals before they even hit a job board. So, ya know, get a referral!!!
How do you get a great referral? You’re in luck! I made a series of videos about it on TikTok, starting with this one:
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3. Build your brand
Okay, this sounds like one of those super-gross things that business influencers say. But go with me here for a minute.
Remember how we were talking about building trust above? Well even if you have a referral, it’s hard to get into people’s heads during the interview process, even if you’re a great interviewer. I’ve been told I’m pretty good at interviewing and reading people, but even for me interviewing can be a bit more art than science.
So what’s another way to get into someone’s head aside from the interview process? One great way is from the referral you undoubtedly got from above RIGHT?!
Another great way though is to read, watch or listen to anything the candidate has put out into the world. This includes things like this Substack here! And OF COURSE any actual product you’ve built.
So get yourself and your brand out there. Build your TikTok following, write on Substack, make a podcast (I’ve done all of those things!) Be on someone else’s podcast, post on Linkedin more…get your thoughts out there! I can tell you for sure that the last three jobs I’ve gotten have been influenced by my thoughts out on the internet. Get out and make stuff! Below is a more advanced variation on that…
4. Side hustle on something you want to become your main hustle
Here’s an excellent video from Prof G on side hustles:
Prof G can be hit or miss I think. But on the point of side hustles being a temporary means to make something else your main hustle, I think that’s on point.
All of my side hustles in the last few years: the AI resume reviewer, building an AI-generated trips app, writing this newsletter…they’re all off the beaten path of what I did before (mostly growth & conversion.) But they all helped me transition to the new career path I’m on working in engagement and AI.
So if you have the time and bandwidth, I’d highly recommend doing a side hustle, mostly for learning and getting versed in the things you want to do ultimately in your main hustle. It helps you stay sharp and gets you to where you want to be.
There are so many new tools now to make something great too! Cursor I love and now use as my main IDE. But things like Lovable, Replit etc. all sound amazing. I’ll be testing them out during my time off!
5. Practice interviewing with ChatGPT Advanced Voice Mode
OMG I love ChatGPT Advance Voice Mode SO MUCH. I spent HOURS with it prepping for interviews. Here is what I did to get the most use out of it:
Upload your resume for context so it knows your background and experience.
Give it a link to the role you’re interviewing for.
Give it links to Linkedin profiles for the people you’re interviewing with.
Paste in any notes that you have from your referral, the recruiter, and any interviews you’ve had, along with notes about the company, their website, etc.
Use a prompt like this one before you start advanced voice mode:
Let’s role play for the role I’ve included above. What kinds of questions would I be asked? Please provide feedback on my answers as well. I’ll trigger voice mode to mock interview.
I’d say I spent 5-10 hours mock interviewing this way and it made me feel so much more comfortable walking into interviews. Do it, thank me later.
6. Negotiate like a boss
If you haven’t read this book yet and don’t have immigrant parents like I did to teach you how to negotiate like a total boss, add Never Split the Difference to your Amazon cart right now:
I read this before I started my 2025 job search journey and was head-nodding through almost all of it. It reminded me so much of watching my dad negotiate buying a car…or pretty much anything he bought. Everything was negotiable, he was always looking for a deal and was polite about it.
Much of what I learned from my dad and what you’ll learn in this book will be critical in a job search. Negotiation of compensation with a job starts from the minute you apply, especially now when salary ranges are posted on jobs. And the negotiation continues right up until you sign on the dotted line. How you negotiate can be the difference between a life-changing job change and a big disappointment. So make the investment to get better at it with this book.
Switching gears on the final leg here…
7. I think I’m finally starting to crack my stress equation
We are starting to crack the code on stress! Here’s what I’m learning might actually work for me according to my Daytime Stress chart from Oura Ring:
I might need connection to feel relaxed and at my best. The chart above was from this past Sunday, where I spent much of the day with family and my kids. Connection is the key to restorative time for me.
Meditation really resets me into a more restored mode. I’ve been hitting the Calm app a ton the last few days and it is delivering at minimum more relaxed moments, if not some restorative time. Brings the heart rate down and keeps me connected to the present moment.
I’m not convinced that watching TV or scrolling TikTok is that relaxing for me. I don’t seem to get into a restorative state with those activities. More experimentation is needed but I think that jives with earlier posts.
I might try more reading and walking. I wonder if the screen time and lack of movement is building up stress. More on these in the next edition.
So if you’re on a journey to live longer, happier and healthier and are thinking about managing stress to do it, here are some pointers that help.
That's it for this week!
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I’ll be back around this time next week with more useful product manager things!