Cracking the PM Code: Aakash Gupta on Building a Stellar Product Career

Did you know that 88% of product management roles are in core PM functions?

What about the specialized roles like Growth, Platform, or AI PM? AI Product Management already represents 5% of all PM jobs and is among the most lucrative.

Aakash Gupta

offers actionable advice on how to break into this rapidly growing, high-paying field.

Whether you’re starting your product management journey or looking to advance, Aakash explains how the scale of a company impacts your role and career path.

In this podcast, Aakash also breaks down the inherent conflicts of the PM role, emphasizing:

“It’s a feature, not a bug, to have disagreements as a Product Manager.”

Learn how to thrive in an environment where the business was designed for conflicting incentives.

We cover:

• From VP of Product to Product Content Creator - 3:48

• Understanding PM Roles Across Different Company Scales - 11:07

• PM Job Seeking Based on Your Career Phase - 16:57

• The Importance of Influence and Decision-Making - 25:36

• Roadmapping and Planning - 32:00

• Navigating Conflict and Stakeholder Relationship - 37:10

• AIPM - How’s The AI PM Role Different From Other PMs? - 44:53

• Separating Platform PM from the Core PM - 50:04

• Breaking into AI Product Management - 53:27

If you're navigating the world of product management or aiming for the next big leap, this episode is your ultimate guide.

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From VP of Product to Content Creator: Journey to a Dream Job

What started as a 15-year climb to becoming a VP of Product at a unicorn startup evolved into a leap toward content creation and work-life harmony.

Aakash’s story is a dream come true. It came with hard work and keeping an eye on the target.

After juggling a demanding VP of Product role while growing his content business and raising two kids, Aakash decided to bet on content creation:

I followed a trend that's happening broadly within the economy, which is the fastest-growing job in America right now - becoming an influencer or a content creator.

Aakash Gupta

This career shift aligned with his core values:

• Control over his time,

• Freedom to choose what to work on

• Work-life balance to spend more time with his kids

• And yes, earning well—because who doesn’t value financial success?

Today, as a full-time content creator, he enjoys the freedom to work on what inspires him and connect with amazing people daily.

Now I feel like I'm just living my best life, doing one job, have work-life balance, getting to come on podcasts and talk to awesome people like you every day.
Aakash Gupta

Understanding PM Roles Across Different Company Scales

In the U.S., product managers (PMs) are evenly distributed across companies of different sizes. According to Aakash’s observations, his audience is split into roughly equal proportions: 20% each work in firms with over 10,000 employees, 5,000–10,000 employees, 1,000–5,000 employees, 100–1,000 employees, and fewer than 100 employees.

This diverse spread contrasts with Europe, where PMs often emerge from digital transformations in legacy sectors or scale-ups like Bolt and Revolut.

Company size heavily influences how product work is structured. Smaller companies require minimal bureaucracy, while larger organizations (10k+ employees) depend on roles like product operations and well-defined frameworks to manage scale. The U.S. dominates in growth-stage companies and unicorns, which contributes to its robust PM ecosystem.

Navigating Your PM Career: Choosing Between Startups and Big Tech

When seeking a PM job, consider how your career stage aligns with company size. Larger companies typically offer higher pay for equivalent titles but demand more experience.