Creating Time And Building Relationships: AI Product Management and the job market:

Join Shobhit Chugh and special guest Aakash Gupta for a transformative conversation on maximizing productivity and strengthening relationships. This event will provide you with actionable insights on:  

• AI’s Impact on Product Management Careers: Discover how AI can help you save time and streamline your workflow.
• Outsourcing with Confidence: Learn the art of delegation and find out how to identify reliable partners who deliver results.
• Top Product Leaders’ Salaries: Get a sneak peek of what the best in the field are earning.
• Positioning for AI Roles: Unlock strategies to build relevant experience and stand out in the competitive AI landscape.
• Leveraged Networking: Master techniques to build connections that drive financial growth.
• Hidden Roles: Explore why the highest-paying product positions are often off the radar—and how to find them.

00:00 Introduction to the Podcast
00:26 Aakash's Early Career and First Product Management Role
06:35 Transition to Growth Management and Core Product Leadership
11:42 Balancing Player-Coach Roles and Delegation Strategies
17:23 The Journey to Becoming a Content Creator
21:11 Monetizing Content and Expanding Influence
25:35 Writing Process and Content Strategy
27:28 Collaborative Efforts in Job Search
27:49 AI's Role in Content Creation
29:18 Insights from Product Leadership Job Search
33:48 The Importance of Recruiter Relationships
38:31 AI in Product Management
40:54 Leveraging AI for Efficiency and Innovation
41:52 Pathways to AI Product Management Roles
47:25 Conclusion and Further Resources

This discussion will equip you with tools to save time, create valuable opportunities, and achieve long-term financial rewards.

Learn more about Shobhit Chugh at intentionalproductmanager.com and connect on https://www.linkedin.com/in/shobhitchugh/

Explore Aakash Gupta’s work at aakashg.com and connect with him on https://www.linkedin.com/in/aagupta/

www.intentionalproductmanager.com

Chapters

• 0:00 Introduction to the Podcast
• 0:26 Aakash's Early Career and First Product Management Role
• 6:35 Transition to Growth Management and Core Product Leadership
• 11:42 Balancing Player-Coach Roles and Delegation Strategies
• 17:23 The Journey to Becoming a Content Creator
• 21:11 Monetizing Content and Expanding Influence
• 25:35 Writing Process and Content Strategy
• 27:28 Collaborative Efforts in Job Search
• 27:49 AI's Role in Content Creation
• 29:18 Insights from Product Leadership Job Search
• 33:48 The Importance of Recruiter Relationships
• 38:31 AI in Product Management
• 40:54 Leveraging AI for Efficiency and Innovation
• 41:52 Pathways to AI Product Management Roles
• 47:25 Conclusion and Further Resources

Transcript

 Ready to move to the next level in your product career. I'm Shobit from Intentional Product Manager. Join me as we discuss ways to help you stand out in your job search and your career, so you can have more impact and make more money. Akash, welcome to our podcast. So great to have you here.  

I'm a big fan of your work, so I'm excited to be here and glad we can chat in a little depth. 

Awesome. So look, probably most of the people who are watching this I'm not going to be watching or listening already know a bit about you, but I would love for you to like, like sort of tell us your product management and founder story.  What happened? How did you get into product? What your career was like, and then this awesome transition that you've made.

We'd just love to hear it from your own, uh, own mouth. 

Sure. I can give you the short version and let me know where you want me to go deeper. So as a  young youth, I was really lucky that my dad was a professor of computer science, so I was enrolled in programming classes from sixth grade itself. Uh, by ninth grade, I was operating an eBay store that I ran my own website on in order to just save some fees from eBay.

I built my own computer. Uh, In college, I was working with a variety of startups in and around the university I was at, and it was really full stack product management, so coding, designing, shipping to production, but spending a lot of time with customers, spending a lot of time with executives saying, this is why we should build it.

What I've now built. And so that led me into my first product management job at a B2B SAS company called scout force, which sold into 40 percent of the D one school. So university of Alabama football team, university of Michigan football team, some of the big money programs, it was their software for their recruiting teams.

If you think about it, they have all these field recruiters.  And I used to go meet with them while they're doing their things. They're going to like football games. Back then they had like, you know,  2012 iPhones. They're uploading their notes. They need like a good way to be able to put those notes in, put their videos into the system.

So we built that software. And that led me down a variety of different product jobs over the years. I went, I was a VP of product at Apollo. io most recently. And that was actually kind of my dream job for most of my product career, working at a unicorn, being a VP of product. That's what I wanted to do. Or so I thought.

While I was doing that, I loved it as much as I thought, but I had kind of a second job, which was  I had already built up my internet presence to such a level that I, I had this like juncture, like, do I want to, which one do I want to do? Because doing both of them,  and I was probably doing them at 90%. A lot of people say, if you do two things, if doing them at 80, I was doing them at 90.

Like I was doing 35 hours pretty much for social media stuff, like five hours at night. I barely slept. I used to do, so my stint would be, I'd put my kids to sleep and then I do 9pm to 2am. And then I'd wake up at 7 a. m. the next day. Sometimes my son or my daughter would wake me up at 6 a. m. or 5. 30 a. m.

as anyone with young kids would know. So, I was living like You know, that true like dual life almost and so for me, it went down into, well, what is giving me the most passion? What would I do even if nobody was paying me? What would I do  just if I had all this time to focus on one, which one would I prefer to focus on?

And then which one has the higher upside? So at that point, I was a VP of product at a unicorn company and I could see a pretty clear. Path for this creator journey to be earning significantly more than I was at the top of the pyramid already. So that was a huge factor. And then loving this work, loving writing content, loving talking to PMs and researching PM things.

That was a second factor and then the third factor being my own boss So  right after I worked at that small startup in Ann Arbor I actually started my own company hired seven people worked for four years on an iOS app called rap to beats And so I've always had that entrepreneurial streak like many other product managers.

So putting all those factors together I had to go out on my own again And give it a shot.  

That's amazing. I mean, absolutely amazing journey. And, um,  um, you know, if you don't mind, I'm going to go like deeper into some of these and like how you thought through the transition and, and, uh, everything around that.

So let's, let's go back. Let's, let's maybe talk about, you mentioned your first product role. Was this like right after undergrad that you, you jumped in, like, was there a career even before that? Yeah. Yeah. 

That was it. That was my first job. So it was a company called Scout Force. And yeah, I was lucky. Like most people, I think that finding a product manager job is pretty difficult, especially right out of undergrad.

Usually those people go for an associate product manager. What I did though, is I targeted a company with only 15 employees. And I didn't just do product management and I worked with them while I was in college. So while I was in college, I helped them ship  tons of features. And I actually designed, I actually did the user research, designed, and shipped them all on my own.

So Having done that they were more than happy to hire me in almost any capacity and they up for my first few jobs They used to give me really nice references and everything like that They just loved me like I was kind of like another co founder in that sense that I like I would just do anything for the Company because I was young at the time as well.

So that's how I secured that job is I was working with them in undergrad They were like, it's a no brainer. We have to bring you into the team. So I got that. 

I love that And then did you like very intentionally chose? Product management is sort of the area you went in. How did that happen? No, actually 

so If you  Think about what I wanted to do is actually found a huge company So what I looked forward to like was specifically like Larry Page Sergey Brin Steve Jobs those types of people really motivated me later on Elon Musk before like Everybody started having million reasons to hate him these people really inspired me And so I was thinking like, that's why I worked with that startup from the beginning.

I just got handed the title product manager because that was the closest thing to what I was doing. Uh, but after that, the first job I actually took was growth manager at a company called ThredUp, which at the time was a Series C company in San Francisco. And Series C is an amazing spot to be because you still get time with the CEO, the CTO, the president.

Uh, Cmo so I actually worked with those guys on growth and it was a series C So we could work on whatever was most impactful. So for my first year, I scaled up a couple things I took their Facebook spend from something like three hundred dollars a month to thirty thousand dollars a month and at better ROIs than it was at when it was at 300 a month.

I scaled up their, at the time, Yahoo ads were still a thing. I scaled up their SEM. So I scaled up a bunch of their growth marketing channels using some of these skills that you now see in me today. So I wrote all the Facebook ads. I remember there was one ad that went, Super viral that had a typo and whenever we would hire like a new brand person, they would always be like, but how come we're spending so much money on this ad?

And we're like, guys, like, this is just how it works. Like this ad has 70, 000 likes. Everybody loves it. Facebook is serving it at a 60 percent CPM. So we would fund these types of posts that I would write. And that was like, uh, that was like the first leg of growth. But as we scaled. Um, our new customer acquisition, we realized like, whoa, like the LTV on these people also needs to go up.

And so that's how I switched into growth product, which is all about how do we take those first time visitors and convert them to first time purchasers. As I built that, I scaled into the pricing system because I realized what's the number one thing that drives conversion? Everybody knows it, right?

Price. If you reduce the price, you're going to get way more conversion. So I slowly made my way into core product, and then I actually started becoming a core product leader. 

That's awesome. You know, just a funny story to share on the one you wrote, you mentioned about Facebook ads. One of my best performing ads, it has this AI generated image, and the image has, like, the person has a monitor.

Two monitors, which the monitors are looking at each other. It's like all weird. And if there's like multiple comments there, which is like how, you know, the first thing you need to do is to hire a real designer and you know, that's how you become intentional. This is clearly not intentional. And I'm like, cool, look at the results on the other side.

So, you know, what works might not be that intuitive.  

Yeah, and at least at the time back when I was an expert, so we're talking now about 2012 for Facebook ads The algorithm it's kind of like it would just find something that it could reliably show to new people that people wouldn't hate I think back then the ads weren't as good as they are now from everybody else, too And so that post it looked organic like most people would comment like  I didn't even realize this was an ad  Because we used this image that was like a blurry image, it looked like, I believe, actually, I took it on my iPhone while I was at our warehouse. 

So I just took a picture of the racks of, you know, the, it was like the fourth generation iPhone, so it wasn't a very good photo. And, yeah, I think that sometimes, you know, that's what I tell people who have, uh, social media, they spend a lot on it, is you have to let those people who are working in the social media space cook.

You have to let them test things out, it might not be exactly to your brand guidelines. But sometimes those things will just pick up and 60 cent ccpm. At the time, the CPMs for the types of ad groups we were targeting was eight $9. So it was like seven 8% of the average CPM because it liked it so much.

That's amazing that, that, that's, that's totally amazing. Um, then, then tell us more about your product journey. So what happened after distant.  So 

at ThredUp, I ended up leading a bunch of core product teams and reporting to our head of product. And so that set the kind of journey off for the rest of my career, where, uh, I was doing basically that reporting to the head of product at places like Epic Games.

Um, at places like Affirm and then at Apollo. So, those roles were kind of the player coach role, where I'd usually have like one product team where I have to do the IC work for, but then like two or three people at the beginning, up until like seven or eight people that I'm managing and also coaching.

And, those roles were really great. Each role that I took,  It led me to like expand my aperture of how I think about things. So from thread up, which is like, you know, two, 3 billion market cap to Epic games, 30 billion market cap to a firm, which at the time it's market cap has varied wildly, but also when it was like peaking in the COVID era, it was around 30 billion market cap.

And then finally to Apollo at a unicorn, which funny enough moved much faster than any of the other companies I'd ever worked at. So, yeah. 

You mentioned player coach. Um, and, and I, I find that a lot of people are in that stage. Uh, tell me more about  how did you make that work? Like, you know, with a core focus for yourself and then combining that with coaching other people.

So any principles or practices that made you successful in those sort of roles? 

Yeah. One of the things that I  I have a really strong belief about that I think not enough people pay attention to is that you need to be advancing What state of the art looks like for PM work products? And so that's why I actually often defended the player cultural even when I was Having like four or five PM's on my team having directors on my team who had people reporting to them I still wanted to keep that closeness because  Ultimately, it's kind of like the founder mode is the current thing, right, about founders.

It's the same thing when you're a product leader. You need to set the bar higher than anybody else. You need to show them, this is really what a PRD could look like. And you know what? A good PRD is not very long. But it is really well written and the insights you're getting from every line and  it is going just deep enough so as to not dictate everything to the designers and engineers, but still have thought out everything that a PM should be thinking through.

So it's impossible basically to like teach some of these skills. Like I think that going from like a nine on a purity to a 10 it takes like Five years of working in product management at successful companies to actually move up to that level So I firmly believe that you know just to actually show teams and also the type of impact So what I find is that a lot of pms they they build their career on safer bets I actually had the strategy of taking like lots of big bets 70 percent of which would fail, but 30 percent of which would change the course of the company.

So I mentioned like the pricing system at thread up the system, ultimately, like it redid our entire pricing. It improved our inventory turns and improved our first new user conversion rate and improves our lifetime value. It was like the basis of the business. Now they have like multiple teams focused just on that.

I just shipped it as one of my many big bets in a quarter. So it, it was like a strategy also. And so to be able to show that to folks.  And then how do I manage this? Okay, so this is why I did it. How did I manage kind of this, these roles? I actually think it's very hard. So I don't think that, uh, anybody who wants to work a 40 hour a week job can possibly do this.

Uh, you have to be able to go totally crazy in your job. So if you have a bunch of  priorities about working out and hanging out with your kids and logging off at 5pm, it's actually impossible. But if you are willing to go the extra mile, you know, my typical day, it would basically look like, you know, eight to nine catching up on emails, nine to five being triple booked in meetings.

And then Sometime in the evening, maybe like for me often, like maybe like eight to 10 o'clock doing some I. C. work where you can show it off. So how can you manage a whole team in just say two hours of I. C. work a day?  Number one, it was really learning how to delegate to my design and engineering partners on those teams, and also kind of picking and choosing teams that could handle that.

So if you have a very junior designer, especially you're like totally screwed on this front,  very senior designer. Who can take a problem statement, they can go talk to users, they can go create a design, they can go test the prototype, they can get all the QA edge cases ready for engineering, then you can rely on them.

So a lot of times I would choose like amongst the most senior product designer, and then an engineering manager who has been Product focused. There are generally like two or three types of engineering managers, but these product focused ones, these are the ones who like, they're leaving a ton of comments in PRDs, leaving a ton of comments and strategies and product reviews, asking questions at product all hands.

Those people I'd pair up with those so that these were the teams where they could just take a couple of really good documents, a really good strategy doc, and maybe PRDs for the top three big rocks and they could run with it. That is super 

insightful because this is probably the, the,  the most common question I get.

Around, Hey, you know, I I'm just really busy. I can't figure out even time for thinking through strategy and others because I'm so busy in execution. And it seems your secret has been, how do I find the right people who actually want to be more product focused, who, who I can delegate these things to. 

Yeah, there's a certain type of engineer who's like, you need to write the tickets for me.

Your PRD did not cover all these use cases. And then there's a certain type of engineering manager who just throws that back in the PM's face. There's another type of engineering manager who's like, okay, we're going to have a tech lead on the team. The tech lead's job is going to be to embed with the product manager.

So they understand the questions that the product manager was thinking about so that they can answer these detailed implementation results. When you have those types of people in place, When you have those types of teams that are autonomous and, you know, a really great example of this is those teams that didn't even need a PM.

You'll often find those like the, the billing platform team or the payments platform team, but they'll be consistently shipping stuff that's improving business metrics. Those can be very interesting if there are some big bats where you can create some innovation in their space to take on. 

That's amazing. 

Okay, so we talked about the player coach role, and now I'm really curious about  transitioning into what you're doing now, like,  just like, where did that idea come from in the first place?  

Yeah, it's serendipity really, or serendipity. surface area of luck increases as you write online. In my case, somebody really amazing, Pavel Hern, really pushed me to create a paid subscription to my newsletter.

So my newsletter was growing very fast, just on the basis of writing I was doing in passion. Uh, like a lot of people like, They're, they're surprised that I could write so much when having a full time job, but it kinda just goes back to my whole life, I'm used to working like 14 to 16 hours a day. The average person is not used to working that much.

They work 8 hours a day, so they look at someone who's working 14 16 hours a day and they're like, Oh, that person must be slacking off in their job. No, actually, I just found time for content when you all were watching Netflix and from like nine to ten o'clock, I would, I had a daily ritual where I would write that.

I would usually write it actually after some meditation so I could clear my mind from work. Finish up all my emails and Slack messages from work, do a little meditation, do my content, head to bed. That was like my ritual. So I grew this free, I have, I think at some point I was the number 11 ranked person on LinkedIn.

Just based on the amount of impressions I'd had, how many likes per post I had. At that time, like, LinkedIn, it was all I was doing. But Paula said, you know what, you need to do this paid newsletter thing. So I, I did that, and having made this amazing connection, he, by the way, is the author of Product Compass, 70, 000 plus newsletters, subscribers, 165, 000 plus on LinkedIn.

He's huge. He's a great friend of mine, so you should have friends who are in similar positions as you. And he's like, look Akash, like, your writing is very suited for this. Because at the time, I used to write like these five, six thousand word articles. Drop a paywall at word fifteen hundred. The people who only are willing to ever read for five minutes, they were never going to pay for your newsletter anyways.

But the people who want more, those are the type of people who are connoisseurs of good information. They're connoisseurs of research. They're willing to pay. And so, immediately found product market fit with this paid subscription. Like, it was just wild. Like, oh my god. People are recommending it to their friends.

I'm not even talking about it and it's just growing on its own. So got this paid newsletter going and that showed me that, okay, I have this product, I had this side hustle that's working for me.  In fact, like the revenue that I'm getting from the side hustle is going to be a lot more than I'm getting as a VP of product.

So I was in that lucky position. Unlike a lot of people who like just have to leave their job and have no revenue, like, especially cause I had kids.  That was never going to be an option for me. I already had like a good revenue plus line of sight to much more if I were able to spend more time.  

Okay. I mean, I really admire. 

Uh, folks who've built this, uh, career, the company around deep writing, you, Lenny, uh, Ben Thompson, who actually was, uh, um, uh, MBA classmate of, of, uh, mine. And I just saw his, his awesome writing. I really admire that because I don't have that, or I haven't built that skill set of Deep, long form writing that you have,  um, it's really awesome.

Okay. Now I'm, I'm also curious, like, you know, as you are this point  thinking about,  or organically, you come to that, but like,  why writing, did you consider coaching, like, how did you find out what was the thing that gave you most joy and then just like decide to pursue it?  

So I thought about the different options.

If you think about how like creators monetize coaching, uh, courses. Books, YouTube, podcasts, writing. So, where I started was like my bread and butter. Like, what was I doing for free, without getting paid, just for fun? Was that deep writing. So, that's where I started everything. More recently, I have started to move into those other directions.

So, uh, released a book last year. This year, I released a podcast. So, I kind of just taking the predictable creator path, you know. So, A year or two from the line, there'll be merch, a year or two after that, there will be, you know, an in person conference. So the roadmap is well trodden, like other influencers have basically already shown us the way and we see also how much revenue they have.

You look at like a Stephen Bartlett of Diary of a CEO, this man's pulling in like 50 million dollars a year. So you see, oh wow, I could 100x my business still, there's a lot more room to go, so.  

I mean, uh, I, I do think this is a very critical point that, you know, both people in careers and entrepreneurship that you don't have to reinvent everything.

There is a  road map. There's something other people have done. And you can, like, just focus on your, I mean, I don't know if you follow the, or, uh, use the term, um. zone of genius and just like follow the other path for, for other people. At least I'm a believer in that. 

Yeah. I think that, you know, the haters on Reddit, they would say like the Powells, the Akash's there's basically two other paid newsletters, Bundon.

And, um, I'm just blanking on the other name, Peter Yang. So like the four of us, they would say like, Oh, you guys are copying Lenny, but no, actually like Lenny pioneered the category. Yes. But he created a category. It's not like in podcasting. Nobody else ever released a podcast like once podcast was created as a really good category a bunch of people entered and actually Lenny Co created the category alongside sub stack and gurgly arose and some of those other people so he was one of the founding members we're kind of all in the second wave these new paid subscribed newsletters and It's fundamentally, it's a space that has so much demand.

If we think about how many PMs there are in the world, there's on the order of four to five million PMs in the world. Lenny definitely doesn't have 400 to 500, 000 paid newsletter subscribers, otherwise he would be living, you know, in Monaco in a high rise. So, He doesn't even have 10 percent of the market really yet.

There is a huge ocean out there. Um, and if you think about it, like at least 10 percent of the market would be willing to pay for something like this. So we have a ton of space to play in. None of us have even started to like, See any sort of like limit on the market demand.  

I mean, it's funny. There's a. A recent, um,  graduate of mine who was like, Hey, one of the things I'm really thankful for is you told me go subscribe to, at that time it was Ben Thompson and Lenny.

And I'm like, like, and, and this person is like senior. So like, I totally agree with you about the  lack of market penetration. Cause like,  I, I believe like everyone should be spending a fair amount on their education. This person was not, not doing that. And they're like very experienced, really smart, smart, uh, on that front.

And it's a great investment for any product leader. So, you know, like let's say Lenny's newsletter, it's 150 a year.  Versus they're probably spending like 1, 100 on a Reforge membership that go take a look at your login stats How many times have your PMs locked into Reforge recently or they're paying for you know 1, 000 for a fertility benefit per year.

They're paying 600 to send people to conferences. What are people getting out of those? Conferences. I'm very curious to know outside of inspiration. So it's a, it's a interesting, like very cheap thing. I personally think, Oh, you mean for companies? Yeah. Yeah. I think most companies, my prediction is that within five to 10 years, most companies will have a learning and development budget.

It was going to be like a hundred percent of companies like a year or two ago. I think this is the end of the ZURP era kind of slowed down the expansion of those, but those were on a crazy upward trajectory right before. The bubble popped and I'm sure it'll continue in a little bit 

now. I'm also curious.

Uh, like, how do you decide  what are you going to write about? And, you know, just also curious about your process. Uh, you, you, I know, I noticed you often speak with other people. What do you go through to produce this, all these awesome articles that people love? 

Yeah, so what to write about, and then my process for writing it.

So, there's actually somewhat joined at the hip, too, so I'm glad you asked that in one. So,  my fundamental  Thing I look at for how to write a post is what have people been asking me about the most where i've been repeating myself the most  So i'm looking for those things like especially I have an engaged slack community for paid newsletter subscribers So they'll be asking me like, you know I might look at like 10 or 11 questions a day Then on linkedin and x people will comment questions in response to my post So i'm seeing all these questions and actually a lot of people also dm me questions on linkedin So all of these Channels i'm getting of questions.

So as I start to repeat myself Then I know like okay, it's time to do a newsletter the other angle I use to write a newsletter Is where is my curiosity taking me and where is there no good content yet?  So Uh, you know, one topic where my curiosity was taking me is like, uh, what is good retention? It turns out Lenny has already written a really good post on what is good retention.

So I haven't gone out and done the extensive research that would be needed to support such a piece, at least yet. Now his piece is getting three years old and I might actually do one maybe early next year. It's on the content calendar right now, but that's how I think about things. And so, uh, For instance, I know we're going to talk about the product leadership job search.

I didn't see any good content out there. I didn't think there was anything actually. There was a ton of content for early career and mid career PMs. But what about late career PMs? And so it naturally makes sense for me to dedicate. At that point, Colin and I, Colin dedicated like roughly like two weeks to that post.

I dedicated like a week to that post. And we collaborated to create the product leadership job search. And so I think Colin talked to something like 16 people. I talked to something like six people. And  the idea there is nothing I publish. I want to a already be online or be an AI, be able to produce for you.

So these days, AI is pretty good. I don't know if you guys know, but, uh, it doesn't need to sound like an AI anymore, especially go try the latest model of Grok or the latest model, Cloud Sonnet 3. 5. Nobody can tell the difference. In fact, there was a recent Turing test done with the latest Senate 3. 5. And the AI sounded more human than humans.

So everybody was saying, this was written by AI, this was written by AI. No, no, no. That was just written by below average humans, which anything now that's kind of below average, we just think it was written by AI. No, no, no. It can fool you. And so for me, it's then, well, what are the unique insights? The AI is not going out there and interviewing people.

The AI is not going out there and doing research. And so that's where I've really tripled down my 

content.  Totally love it. And it's, uh, uh, I am also consistently amazed. I'm also consistently amazed how much I can get AI to start sounding like me  and like, by training it and then be like, Hey, you know, like literally at the gym, I would be thinking of something and I would be like, Chad, GPD, please come up with the draft.

And I'm like, okay, it's 80 percent there. Now I'll edit it later on and, and get it somewhere. So that part is also, uh, super amazing. 

Yeah. Yeah. It can get you 80 percent there in like 10 seconds. And so your timeline to get 200 percent is a lot faster. 

I agree. I totally agree with you. Um, okay. That's awesome.

So, so let's dive into like two areas that, um, in my community, um, people have been posting articles for a long time. Uh, but like Two,  two of them really like sort of blew up and everybody was commenting and bunch of things. I want to talk, talk to you about some of them. Uh, first. So let's start with the, um, leadership job search product leadership job search.

Uh, if you were to think of like, as you interviewed  these people, what were like some of the most counterintuitive things you, you learned that you were like, wow.  

Yeah. So.  That's generally my bar for publishing even like 10 words on my newsletter. And this is a 20, 000 word article. So I'm going to choose the best of the best of that article.

So like the maybe like three sort of most wow aha moments for me. One, 70 percent of product leadership jobs are never listed online.  Two, a similar percentage About 70 percent of product leadership jobs as a result are filled via recruiters. And so having really good relationships with recruiters is very, very important.

And then third, the salaries and types of percentage of companies people are getting actually blew my mind. I think, uh, even when I was a VP of product at Apollo, I thought I knew what Uh, CPOs were getting paid, but I was, I was off. I was under because there's a lot of data out there, but all that data is wrong.

It's way, way under the data is telling you like, Oh, these CPOs at Series C are making like, you know, 300 K and getting like 0. 5 percent of the company. No, like it's actually way, way more. The range is anywhere from like 425 to 600 in cash. And anywhere from like half a percent at the very low end to like one and a half Percent of the high end.

So people are making way more money than you think at the top. Those are three of my big 

ahas. Love it. Love it. And, um,  I'm curious going deeper into like, especially the first two points. When you said 70 percent of product leadership jobs are not posted. This is primarily a certain stage of the company or is it across the board? 

Yeah, so there are a few public companies that have like a policy that all jobs need to be posted online,  even those jobs,  70 percent of them are filled well before they're posted, there's either an internal candidate, or there was a recruiting person, you know, if you look at a company like HubSpot, so I got the opportunity to work with HubSpot's head of people at Apollo, and we made a bunch of key hires on Apollo's product team, you know, his approach, he built five, six, seven year relationships with hotshots and product.

And then when he'd go to a company like HubSpot or Apollo, he would sell them slowly and he would make the leader sell them. So he'd tell me like, Oh gosh, like this is one of the hotshots. He's like, you know, a target for your team. Like, you know, he's led product growth that Miro he's led product growth that gong, like he's going to be a perfect fit for Apollo.

So you should go get dinner with him. And I wouldn't even be about having a job yet. It would just be like, Slowly cultivating into it. So that's how these, uh,  these truly excellent companies are sourcing. Excellent high level positions. And so the percentages decrease. So if we're talking about the head of product, CPO SVP.

Even at like a Google or something like that, 0 percent of those jobs are listed. The only ones listed are the ones that are required by HR policy. Now, if you go down all the way to director at like a series, a company, then it's only 60 percent of the jobs.  are listed. So we go, we go see way more jobs listed.

So the smaller the company, the lower the title, the more likely it is to be listed.  

Got it. Got it. That's, that's super interesting. And, um, speaking of HubSpot, um, I actually interviewed with them for a VP role way back when, and then they decided I'd be not going to invest in this area yet. And how did it happen? 

I knew the CPU, the CPU was like, I read this article you wrote really cool. Want to chat about it? I'm like, cool. That's awesome. Let's do that. Comes over for lunch. And, uh, it's like, oh, by the way, we are hiring this person. I'm like, Ooh, okay. Let's talk. It's a great company. I, I would have loved to work there. 

Um, now, you know, the second point, um, building those relationships with the recruiters, um, there is a perception, at least,  I've sensed from my community and a bunch of others that, oh, recruiters are very transactional. Unless you're a good fit, then it's not going to work. I'm just like curious,  what, what did you find out in your research and writing on this topic?

Yeah, I didn't find them to be transactional at all. Just as an example, almost every single recruiter I reached out to as a part of this piece responded to my questions within that same day. I go out and do research. I send cold DMs every single day, and no class of people responded faster. more timely than recruiters.

So to think that they're transactional is like a very broad mischaracterization. And if we're talking about the recruiters who are filling high product jobs, these people are incredibly well paid to think that like you could, uh, you could, these people are as good as your best CPOs and VPs of product.

Okay. These guys, they're the ones who you see. See at the yacht club on the phone, talking about 800, 000, this 0. 1 percent of the company, these, that's who they are. Those are those people, a lot of these guys, they're called million dollar men, because their goal is to make 1 million in comp. If they hit that by August, they'll just stop working for the next four months. 

You know, that's how these guys operate their life and gals, actually, a lot of them are gals. So, uh, No, definitely not. Um, all the best product leaders, everybody, you know, who's gotten a CPO job or SVP job has a network of recruiters and  the, to varying degrees, they all support that network. The most  common and effective tic tic to use is that recruiter is going to ping you.

Okay, uh, Shobit, I think you would be great VP of product at HubSpot, but you're currently not looking for VP of product at HubSpot. So what you do is you pay, you text three of your buddies,  Hey, Ranjith, Akshay and Alyssa, are either any of you guys interested in this VP of product at HubSpot job? I have a lead.

Alyssa responds right away. Boom. You say, okay, can you just customize your resume? I know they really care about this. She sends you your resume, you follow that back to the recruiter. And also you do this within like two hours. You don't, recruiters respond fast as I said, right? So you don't wait like 48 hours to do this extended process.

But you immediately come back and recommend Alyssa. And it turns out Alyssa gets hired for the job, right? Because you actually know who the good talent is. And you can recommend and you can become that person who, you know, When Alyssa got hired, that recruiter got paid 80k. So, she got, he, they got paid nicely.

They're gonna remember you after that. They're gonna ask you for again and again. And you can maintain these relationships. And then at some point, you'll be the person who they actually ping when they get new roles. And at some point, that new role will be your role. And you'll say, you know, who's the candidate?

Me, I wanted to always work for meta and now you have a director role and you know, that's the level I'm targeting and you know, I've never made that seven figure comp. Here's my chance. Let me talk to them.  

Okay.  If I were to boil this down, I think it's a very important insight. It's like  people, you've got to play the long game here and you're going to just be willing to help and know it's going to come back to you. 

Yeah. Yeah. I mean, with karma, with these types of universe. Things where you're just helping the universe, you know, you have to put out 10 times more than you're gonna get back You just have to be okay with that ratio 

Yeah,  I mean, I don't know over the long term It feels like for most people you'll get back like even more but on a short term Yeah, like, you know don't expect it and tomorrow they'll have the job.

Yeah and I mean if you maintain relationship with 10 recruiters, you know, you're only gonna have like seven or eight jobs in your career or like three or four of them might get filled by those people, but  More likely than not, just one or two of them will, but that's great that you got one or two of your key jobs filled by a recruiter.

You know, the other ones, they should come in. Just inbound because you're developing such a great background. Anyone who has a good background in product knows that you're getting inbound. So if you're not getting inbound in product, there's one of two problems. One, the brand, the companies you're working for aren't sexy enough.

Or two, you don't have enough years of experience. That's it. I've seen people with the least optimized LinkedIn ever, but they've been at Uber PM for seven years. They get inbound every week or so.  

Agreed.  Totally agree. So let's talk a bit more about, um,  a recent article you wrote about AI in product management. 

Again, I'm going to ask you the same question because, you know, you, you, you, you think the same way. What was surprising as you did your research and start to write things out?  

Yeah. So again, this is another one of those, I think like 9, 000 word article. I collaborated with Marilyn Nika, who was an AI product lead at Meta and Google.

So she was the highest she runs a 

Maven course as well. 

Yeah. So she basically knows the IPM job market. So, uh, I basically tried to get every insight out of her that you might get if you were to pay her for many, many coaching sessions. And then. I also coached a bunch of VMs to getting AI VM jobs. So this piece took me, I think, seven and a half months to create.

You'll have to fact check me on it. I say in the article exactly how many people we get VM jobs, etc. But, you know, we got people jobs at Databricks, people jobs at OpenAI, Anthropic, Google, Meta, and of course the biggest hire, Microsoft. So many people getting Microsoft AI jobs. Because we know Satya knows how to invest, right, in a new area.

And he laid off all those people in the gaming division to fund it. So there was, uh,  the first aha moment for me after doing all that research was  There's absolutely no concern about AI for product management. There's literally none, you know, like everybody was worried for a second there because, uh, GPT two to three to four in two years was amazing.

I agree with everybody, but you know what? GPT five hasn't come out. GPT 4. 0 is not a big step up. Code Interpreter is not a big step up. We have not seen a GPT 5 level advancement, even though I did name check Grok and Sonnet, which are two really competitive models now. Um, even the latest version of Gemini, so I teamed up with Liam Bolling over at Gemini, the PM there, even that's very competitive and very interesting, but none of them have been a step change.

In fact, as we were just talking about earlier, what they're really good at,  is taking you from 20 percent to 80%. They can't do the beginning and they can't do the end. They kind of suck at both. They're not creative and they don't sound like humans, right? So  what is AI useful for? Well, first of all, it's making your developers more efficient.

Second of all, it's making your designers more efficient. Third of all, it's making you more efficient. PMs are using it for PRDs, for strategy documents, for responding to emails, for taking meeting notes, for sending out meeting summaries, for doing analysis on experiments, for creating bandit algorithms to better quickly.

select the winning AB test scenario. So that's what PMs are using AI for today. And you know what? It's meant there's more PM jobs. You know, uh, there's this crazy data that came out, right? Where in 2021  PM jobs peaked after 30 years of nonstop growth, PM jobs peaked, but you know what? You know why it's not down 10 percent because actually like probably 10 percent of PMs were laid off. 

It's those AI jobs. This came in and that's why it's only down 1 percent because we saw basically like a 9 percent lift in AI jobs at these companies I mentioned like Databricks, Microsoft, all these companies are hoovering  up tons of talent. So that was my big aha. So when I had that aha, my next question was, okay, all UPMs who are laid off, For all you PMs who don't have AI experience, how can you position yourself for one of these AI PM roles?

And so what I learned at the first AHA is AI is the one place where side projects work. I don't think side projects work super well for your average PM job. If you have worked in retail and you want to move into fintech, you can't suddenly build a fintech side project.  You know what? You could build a pretty good AI side project.

Or you could at least build something that shows that you're really using the space. Or you could become a content creator. So a lot of people, what they do is that as a new model is released, they'll create a cool use of it. And then they'll get caught up in these Twitter and X threads where they compile the greatest uses of all the new models.

So you see lots of people like this, like Amar Rishi, who's now head of design at 11 labs for every cool new model. He used to release a little usage of it. So he went from being a regular designer to now being head of design at one of the hottest companies in the world. I saw many other people with very similar trajectories where they're using their side project.

They're hacking on the side. They're hacking with AI. They're the AI hacker. They're using AI to build an AI product. Those people are often getting these AI PM jobs. So that's route one. Route two,  you know, even if you're a core or a growth PM, how can you use AI in your surface area? How can you use AI in an innovative way?

So not just querying the open AI APIs because there's absolutely nothing that you've done innovative or interesting about that.  Maybe, you know, You've fine tuned the GPT 3 Turbo models to be more effective than the GPT 4 0 and faster so that you can deliver for your company at 1 percent of the cost and twice the speed, really good AI results for your users, that 90 percent of users accept those AI results.

That's something that's very interesting. And so much. Believe me to get to 90 percent user acceptance. That means you, you spent years on it of iterating, improving your prompts, improving your fine tuning, everything like that. So if you go and build those features, that's another really good route. And so what I did over the six, seven months that I was working on this piece, I actually worked with real PMs where we would try to build like proactively think roadmap, how are we going to get an AI feature?

So that then when we go interview at Anthropic or OpenAI, we can talk about how we are, like, on the cutting edge of innovating product with AI. 

What you just mentioned here, um, it, like, for me, seems to solve two big things that product managers always talk about. Well, one big, it solves one big thing, and then there's a second point that's very important.

First big thing is when you're talking about, hey, I'm too busy,  This is your opportunity to find that time for strategy because you can leverage AI to do some of those things that you would have just spent hours doing.  And, uh, those would be like, you know, the, the, the low importance tasks for you.  And then second, like becoming a super user of AI. 

Seems to be like just cool for you to have like even a ticket to entry to get an AI product management job.  

Oh, yeah, and I think you have to code also. Every single AI company out there They want people who are technical, who can code, who can ship. I believe every single open AI PM that I know that's gotten hired can code.

So if you want to work at  Probably the best TC job there is, you know, that's probably going to be a two, 3 trillion company at some point. It's only valued at a hundred billion right now. So you're going to 20, 30 X or equity plus their cash offers are higher than Google and meta. I mean, if you want to work there, that's, it's the sexiest job I believe currently in tech, you have to be able to.

So I think it's a prerequisite. I tell every single buddy that Andre Carpathy, he has a YouTube course. He helps you code. GPT 3. Everybody should be doing that.  

That is really next level and it feels like,  uh, the product managers who are getting into AI have many levels to go through in the technical expertise, but they don't have to necessarily hit that top level right now  to have the initial move. 

But like for something like OpenAI or Anthropic, you need to get to that level. 

Yeah. Ideally. Ideally. I think that, uh, you should think about it as.  How am I going to find 2 3 hours a day for the next 6 months?  To hack around with AI products, release AI products too. So go ahead and take a look at Levels.

io. This man has, what, three AI products currently generating over 50k MRR? How many do you have? You know, everybody listening. Generate even one with 500 MRR and you'll learn a lot. So, this man is releasing one a month. You know, Mark Liu is releasing one of these once a month. There's no reason you can't also.

Uh, the current state of Cursor plus Claude Sonnet www. levels. io is amazing. You can build apps fast and as a PM, it's really good for you to understand design as well. So, uh, use Playground AI to create your first version of your design, take it over to Figma, learn your Figma skills, improve it a little bit, and then ship.

Amazing.  

Well, Akash, I, you know, this has been like, Uh, such amazing information. Like I was taking notes while, while talking to you. Like I learned so much today. Thank you so much for appearing in, in today's podcast and for our viewers, like, how did they learn more about you? Uh, how did they get to know some more of your content?

Uh,  uh, tell us more. 

Sure. Yeah, so I think like the two ways. Number one, subscribe to the newsletter. Uh, even better if you wanna subscribe to the paid version. And if you need like a discount of some sort, just email me. You can just reply to your welcome email. I read all my welcome email respondents.

Actually, I read all my email respondent. And then second, um,  listen to the podcast, uh, just launched about, what, a month ago? Twice a week podcast going like two and a half, three hours each recording session going super deep on product topics. So I was already doing this research already. And so all my friends kept telling me like, if you're already doing it, why don't you just put it out on the internet? 

Yeah,  love it. Thank you so much, Akash. Really appreciate it. 

Thanks for having me and, uh, look forward to the next collab. 

Hey, be sure to check out our website at intentionalproductmanager.  com to see how you can level up in your career.