From Product to Profit: Tech bro learning sales | Update | Day 29 / 100
Insights from my insomnia episode this week.
It’s 3am Saturday morning. I crack open an enterprise sales textbook, hoping its dry pages would lull my restless mind to sleep.
Instead, I find myself captivated, highlighting paragraphs and nodding along the pages.
I make a new section in Notion and start taking diligent notes.
I eventually pass out at the break of dawn and finish the book the next day.
I never thought I would enjoy this book, yet I couldn’t put it down.
Could I…actually be enjoying learning sales?
I believe the answer is yes.
Enterprise sales lessons reminded me of preparing for product management interviews in college.
A sales rep’s preparation for discovering, qualifying, and presenting to a potential customer seemed so strikingly similar to the guidelines and frameworks that landed me final round interviews at Google and Facebook’s prestigious entry-level PM programs and a senior product offer from TikTok.
My insomnia this week has been the worst it’s been in a while, but fortunately something good came out of it.
Let me lay it out for you.
There are at least 4 distinct areas where excelling in sales is analogous to conquering a PM interview.
Be tactical.
Great salespeople are prepared for a variety of responses. They gracefully handle objections and reluctance to take a follow-up by demonstrating the direct or opportunity cost the prospect is incurring by not considering their solution, and push along their plan. They are prepared to answer questions like “can I just get some information sent to my email” or “I don’t have the budget”, and will have even built well-crafted responses to these concerns over time directly into their sales deck to pull out when the time is right.
They walk into the meeting knowing what they could be hit with, and revise their shortcomings and collect patterns when they encounter something new.
This tactical approach was immensely refreshing, as it is exactly the same as preparing for product questions.
During college, I’ve come to collect a series of guidelines, frameworks, and even intentional pause-inducing phrases over time. I found that creating a consolidated document of various scenarios and refining them with each interview personalized for myself gave me the best chance to succeed.
The stakes are high in both — a sale worth more money than I can count or a job offer that can catapult my earning potential, so why not prepare for all the possibilities?
Make yourself incredibly clear.
One thing that’s always recommended for PM interviews is bullet pointing your responses.
“There are three aspects we will evaluate our proposed solutions across: total addressable market, technical feasibility, and confidence in success.”
It tells your interviewer 3 things immediately: 1) you can communicate, 2) you will be talking about exactly three things, and 3) here are the exact three things you will be talking about.
You then would proceed to repeat yourself as you dive into the details of these three hypothetical categories, and summarize the three points again at the end.
This is a rudimentary PM skillset: communicate clearly to guarantee understanding.
A sales presentation, as I have learned, is structured the same way: clear visualization of problems that your decision maker faces, a list of products that undeniably tackle your decision maker’s problems, and ideally undebatable proof that your solution works and thus you’re not talking out of your ass.
Sales presentations are built with visuals and marked texts with the sole purpose of ensuring the prospect both gets the problem AND how your solution fixes it.
The one thing you and your prospect do not have in common is that you understand way more about your product than they do, and it is your job and your job alone to make sure they understand how your product solves their problems.
Keep them engaged.
If you got a “Design a product for XYZ” or “Improve product X” problem in your PM interview, a sure fire way to burn your chances is to yap about your supposedly great solution for 15 minutes straight and then ask “Does that sound good?”.
Your interviewer would say “Yeah that sounds great” as they hurry to switch tabs back from their actual work.
Checking in and re-engaging your interviewer is vital to getting your points heard whenever you go on for more than 2-3 minutes.
It’s the same reason standup comedians ask questions in their crowd work so nobody gets distracted.
Same goes for sales presentations.
When I was toying around the mental health space for potential business ideas, I took a demo meeting from an EHR software company to check out their software. The sales rep presented his screen and proceeded to click buttons on their software. He talked nonstop for the next 20 minutes, and I promptly turned my camera off and started to do my own research.
Keep you audience mentally clocked in. It doesn’t matter how good your product is if your audience didn’t hear it.
Time is of the essence.
I’ve come to learn that sales is not only a numbers game but also a game to intelligently allocate your time (thanks Elyas!).
The game plan is to determine as quickly as possible if your prospect actually has the problem your product solves (this is what the qualification step does). If they do, then you want to demo in front of the decision maker as quickly as possible and drive to sale. If they do not, then you want to quickly and gracefully end the conversation so you can move on to others who may be qualified.
You only have so many hours in a week, and 30 minutes saved on a prospect who will never convert is 30 minutes gained in discovering and creating more leads who may.
This mimics a PM interview beautifully, because the clock starts ticking the second you get into the interview.
In the 30-45 minute allocated, you will need to build rapport, solve 1-2 product questions, and then ask questions for yourself. You must leverage every minute to demonstrate you are indeed the rockstar they have been missing, and that means running through an efficient problem-solving framework and avoiding situations where you go back to the drawing board.
5 minutes spent rambling about nice buttons on Instagram Reels with no point to be made is 5 minutes taken away showcasing your understanding about success and guardrail metrics.
The silver lining.
The one thing I’ve known for a while, and reinforced by the book, is the ability for great salespeople to be polite yet persistent (if the prospect is qualified). To be that annoying little rat who won’t take no for an answer and constantly drive to demo calls or to get the decision maker cc’ed on an email.
Admittedly, being unfazed in the face of nicely- or rudely-worded rejection is not my current forte.
I’m accustomed to designing, implementing, and evaluating solutions that should work, because their failures implicate my ability to make good decisions.
This will be an aspect of sales where I’ll have to bring back in that all-in mindset.
Lots of practice by myself, with a friend, and on real calls will be a must.
I’ll need to get comfortable with the 80-90% rejection reality and this will be my biggest barrier to improve at sales.
A happy feeling.
All things considered, learning about how to do sales has been great.
I’m starting to reap the benefit of being that “jack of all trades” engineer.
It’s not just about having the best product, but also about showing diligence, tact, and preparation in more ways than one. I have a fairly optimistic outlook towards this because I’m used to pulling in expertise from my various prior career interests.

I felt a slight jolt of joy as I wrapped up the book (It’s called Founding Sales for anyone interested in learning more).
It’s going to be fun, because my mojo is finally coming back online.
A quick side note.
This is my first and last “Update” post. I no longer think it’s productive to segment my posts by “Reflections, Ideas & Perspectives, and Updates” as I had planned in my first post.
Why? Well, because they’re useless. I was originally inspired by recommendations on email structures to investors, and I’ve come to realize that personal content are and should be different.
I’m neither writing to impress nor sharing concrete thought leadership, so let’s not pretend that’s what’s going on.
I was wrong in making the initial judgement call (public admission?? sheeeesh). I’ll continue to track my days, but posts will no longer contain this fit-a-square-peg-in-a-round-hole label crap.
Let’s keep it simple, there are bigger problems to spend time on (like actually getting this business rolling).
Thanks for reading!
JZ, May 13 2024