Over the past month, I reviewed 100+ career questions submitted through Nikhyl.AI (powered by SuperMe). The pattern was unmistakable—everyone’s paralyzed by the same fundamental anxiety:
“I’m a Director at a FAANG company and recruiters keep reaching out about senior IC roles. These used to feel like a step backwards, but now they’re positioning them as better opportunities.”
“I’m in middle management. I’m setting vision and strategy for my team, not the company. How do I stay relevant when I’m neither strategic nor hands-on?”
“After two failed startups where equity went to zero, I need something stable. But every ‘safe’ opportunity feels like I’m giving up on being part of the AI transformation.”
These aren’t just career questions. They’re symptoms of an entire profession grappling with a fundamental shift in how products get built, how companies scale, and what skills actually matter.
Why Product Managers Need to Upgrade Their Intuition
Let me be direct: Product managers get paid for their intuition. Your value comes from understanding how products should be built, what customers need, how teams should operate. That intuition—built over years of experience—is becoming outdated at an unprecedented rate.
Why? Because the fundamental math of building products just changed.
Companies used to scale by hiring people. More people meant more managers. More managers meant layers. Getting promoted to management meant you’d made it. The entire PM function emerged to manage this complexity—coordinating between teams, aligning stakeholders, building processes.
But we’re rapidly moving toward a different reality. One person with AI will soon do what ten people did before. Companies are beginning to scale through technology, not headcount. Flat organizations are shipping faster than hierarchical ones. The distance between idea and execution is collapsing from months to days.
This has profound implications for product management:
The PM function is being introduced later (you don’t need PMs to coordinate 5 people)
PM teams remain smaller (AI provides leverage that people used to provide)
PMs must be far more hands-on with customers and product (less managing, more building)
As one founder told me: “We’re 18 months in with $50M ARR and just hiring our first PM. Five years ago, we’d have had a team of ten PMs by now.”
The uncomfortable truth? Your intuition about how products get built—formed at Google, Meta, or that successful startup from 2018—assumes a world that will no longer exist. And that world isn’t coming back.
This is why I tell everyone the same thing: You need to take one step backward to take two steps forward. The “step backward” isn’t really backward—it’s paying tuition to upgrade your intuition.
Understanding What Companies Actually Want
Before we dive into your personal constraints and capabilities, you need to understand how the market has bifurcated. Companies hiring PMs today want one of two completely different things from their leaders:
Type 1: “Be Our AI Strategy”
These are traditional companies—successful businesses with real customers and revenue—watching AI transform their industry. They have scale but little AI vision. They’re desperate for someone to essentially BE their AI strategy.
Think enterprise SaaS companies, growth-stage startups, traditional tech companies. They need a PM who can:
Identify where AI can transform their existing product
Build conviction in the organization for change
Navigate the politics of transformation
Make them AI-first without breaking what’s working
Shepherd in change and redefine org structures
Critical point: These companies need you to be a transformation expert. You’re not building AI from scratch—you’re figuring out how to integrate it into an existing business.
One PM who successfully made this transition told me: “They didn’t hire me because I knew LLMs. They hired me because I knew how to get 500 engineers to change how they work.”
Type 2: “Scale Our AI Vision”
These are AI-native companies that have found product-market fit. They have breakthrough technology, a bold vision, and early traction. They need someone to build the operational machinery that turns vision into products at scale.
Think OpenAI, Anthropic, Sierra, Decagon, or any hot AI startup. They need a PM who can:
Work with a radically different product development process
Ship at unprecedented speed with tiny teams
Connect product with AI research (a new discipline for PMs)
Deeply understand the customer and their future needs
Build structure without destroying what makes them fast
Critical point: These companies don’t need another AI visionary. They have founders and researchers for that. They need someone who can execute in their unique environment.
As one AI startup founder put it: “I don’t need someone to tell me what to build. I need someone to help me ship it 10x faster.”
The mismatch happens constantly. The enterprise PM joins an AI startup expecting to “drive strategy” and discovers the strategy is set—they need execution. The startup PM joins big tech to “build AI products” and discovers they’re mostly managing stakeholders and fighting for resources.
The Three Constraints That Actually Matter
Now let’s get personal. I’ve learned to start every career conversation by understanding constraints. Not aspirations—constraints. Because your constraints immediately eliminate certain doors while highlighting others.
Constraint #1: Compensation (The Reality Check Nobody Wants to Have)
Let’s address the elephant in the room with real numbers:
“I’ve been at Google for about five years, currently leading a technical team. The challenge is that leaving Google means taking a significant pay cut—I’m probably making 2-3x my market value.”
If you’re at big tech benefiting from the stock run-up of recent years, you’re likely making 2-3x market rate. I call this a ‘harvest’ position—you’re there to maximize compensation, not primarily to learn. And there’s no shame in that.
But understand what you’re harvesting. As one director told me: “I’m staying at Meta for exactly 18 more months. That funds my kids’ college. Then I’m taking a 50% pay cut to actually learn again.”
The Equity-Burned (The Other Side of the Story)
Then there’s the opposite problem—those who’ve been chasing the startup dream and have nothing to show for it:
“I’m 37 with no significant savings because I kept joining early-stage companies. Everyone talks about ‘investing in learning’ but I need to invest in my 401k.”
I see this constantly. You joined that Series A in 2015—it went nowhere. Then the “hot” startup in 2018—acqui-hired for pennies. The pandemic-era rocket ship in 2021—ran out of runway. Meanwhile, your college roommate who joined Google is sitting on $2M in vested stock.
The psychological toll is real. One PM told me: “I’ve been at three startups over 10 years. My equity is worth exactly zero. Friends who stayed at boring big tech jobs are millionaires. I feel like an idiot.”
If this is you, you need liquid compensation NOW. Not options that might be worth something in 5 years. Not paper money at a $10B valuation. Real, liquid compensation that pays for your kids’ braces and your mortgage.
The New Middle Ground
The good news? The market has evolved. You’re no longer forced to choose between big tech golden handcuffs and startup lottery tickets:
Later-stage with liquidity: Stripe, Databricks, and similar companies offer secondary markets. Your equity has real value, not just hope
Public growth companies: Beyond FAANG, companies like Klaviyo, Hims & Hers, and dozens of others offer real equity with liquidity
AI compensation reality: The top AI labs and startups pay well, but they hire very few applicants. And these AI startups’ equity is a wild card—the valuations are arguably bubblish, but the potential upside if you pick right could be generational wealth
Talent acquisitions: For founders, acqui-hires are back and paying well
Here’s the framework: Be brutally honest about where you are financially. If you have high compensation needs (kids approaching college, aging parents, mortgage in expensive market), you need to either:
Stay in your harvest role and maximize it with a clear timeline
Target the new middle ground—companies with semi-liquid equity
Accept that certain doors (early-stage startups) are closed to you
Stop torturing yourself about opportunities you can’t actually afford to take. There’s no nobility in taking a role you’ll have to leave in six months when reality hits.
Constraint #2: Location (The Geography of Opportunity)
“I’m a product leader in Austin and every AI role seems to require SF or NYC. I’ve built my whole life here—kids in school, spouse with a local job. Are remote senior roles basically dead?”
The location reality has fundamentally shifted:
AI-Native Companies: Overwhelmingly in-person, heavily Bay Area concentrated. “Interviews are on Sunday” because everyone lives within 20 minutes.
Big Tech: Hybrid is the new normal (3 days in office), but fully remote roles are shrinking, not growing. Still more flexible than pre-COVID, but the trend is clear.
Traditional Companies: Most flexible, especially for senior roles. Your best bet if you can’t relocate.
But location isn’t just about where you work—it’s about where decisions get made. One PM learned this the hard way: “I thought I could do the role remotely from Austin. But all the real decisions happened at Sunday dinners in SF. I was always playing catch-up on Monday.”
If you can’t relocate to the Bay Area, you’re eliminated from probably 80% of AI-native opportunities. That’s not a judgment—it’s just reality. Focus on the 20% that remain viable.
Constraint #3: Pace (The Hierarchy of Intensity)
“I want to transition to AI but every role seems to require 60-70 hour weeks. At 42, I value my health and family time. Are there ANY AI opportunities with work-life balance?”
I see three distinct pace modes in tech, and you need to be honest about which one you can sustain:
9-9-6 (Work Is Life)
AI startups where Sunday interviews are normal
Young or first-time founders who are married to work
No boundaries—work is priority zero, everything else comes after
Incompatible with parenting young kids, caregiving, or health issues
Online After Hours
The norm for most tech jobs, including big tech
You’re on Slack at 9pm but can establish some boundaries
Intensity comes in waves (launch periods, incidents)
Includes OpenAI, Meta during crunch, most growth companies
Sustainable with discipline and clear communication
Avoid Nights and Weekends
Co-workers sign off at 6pm, no weekend expectations
Established projects, lifestyle businesses
Usually means slower growth, less cutting-edge work
Hard to “stay current” working here
But gives you time to invest in learning elsewhere
“Everyone talks about ‘founder mode’ and working harder. As a parent of young kids, I literally cannot work weekends. Am I just not cut out for startups anymore?”
You might not be cut out for 9-9-6 startups. But there are plenty of “online after hours” opportunities where you can thrive. Stop applying to roles that require a pace you can’t sustain—you’ll either fail the interview or burn out within months.
The Builder vs Manager Identity Crisis
After compensation, location, and pace, we get to the heart of the matter: What are you actually good at? And more importantly, what energizes you?
“How do I position myself for AI-focused roles when I don’t have direct AI experience? I’ve been managing teams for five years, and while I understand AI conceptually, I haven’t actually built with LLMs or shipped AI features.”
Here’s the framework that matters: You’re either a Builder or a Manager. The middle is disappearing. For 10+ years, the pendulum swung toward managers—they got paid more, were seen as more senior, and became prerequisites for any leadership role. Now it’s swinging back.
Builders: The Obsessed Craftspeople
Builders are obsessed with the craft of building products. They:
Always have an opinion on how to improve the products in their everyday lives
First to use the latest AI tools
Are constantly rebuilding how they work
Get energy from being in the details
Focus on the car, not the factory
One critical insight: Many excellent Builders got promoted into management because they were so good at their craft. They became what I call “okay managers but great individual contributors.” Their teams might be small now, but their instincts remain Builder instincts.
As one VP who took an IC role told me: “I realized I was happiest when I was closest to the product. Management was something I did because it came with the territory, not because I loved it.”
If this is you—if you think about product details in the shower, if you’d rather prototype than run a planning meeting—you’re a Builder. The market is swinging back in your favor.
Managers: The System Architects
Managers are obsessed with scale and leverage. They:
Think in systems and processes
Get energy from making teams work
See patterns across problems
Excel at building through people
Focus on the factory, not the car
Great Managers might not write the best PRD, but they can orchestrate ten people to ship something exceptional. They thrive on organizational challenges, talent development, and strategic alignment.
The challenge is particularly acute for middle managers:
“I’m in middle management, setting vision and strategy for my team, not for the company. I’m not directly working with the new age of product management. It’s a weird time to be a middle manager.”
You’re neither strategic enough for the C-suite nor hands-on enough for the new world. The comfortable middle—where you could be “strategic” without being hands-on, where you could “manage” without operating the business—is vanishing.
The Dangerous Middle: Wannabe Builders
This is the most precarious position in today’s market:
“I’ve been trying to get more hands-on by taking online courses and building side projects, but companies still see me as a ‘process person.’ How long does it take to rebuild your reputation as a builder?”
Here’s the hard truth: Taking an AI course or watching YouTube tutorials won’t make you a Builder. Building requires obsession, not education. If you’re not already building things on nights and weekends because you can’t help yourself, no job will magically transform you into a Builder. Real Builders? They’re shipping side projects, contributing to open source, or building internal tools at their current job—not because anyone asked, but because they can’t help themselves.
I see too many people in this position:
Taking prompt engineering courses
Getting AI certifications
Attending hackathons they don’t enjoy
Hoping a job will teach them to build
It doesn’t work. As I tell them: “A class isn’t going to make you into a Builder. You need to have the obsession to basically be one or the other.”
If you’re a wannabe Builder, you have two honest options:
Commit fully—come up with something to build and start getting your hands dirty
Embrace being a Manager and find organizations that value that
Which Door Can You Actually Walk Through?
Here’s how the math works:
High constraints + Manager DNA = Big Tech Harvest
Stay at Meta/Google, maximize compensation, plan your exit
You’re not upgrading your intuition, but you’re funding your next move
Low constraints + Builder DNA = AI Startup IC
Take that “step backward” to senior IC
It’s not backward—it’s tuition for upgrading your intuition
Medium constraints + Manager DNA = Transform Traditional Company
Be their AI strategy
Good pay, sustainable pace, real impact
Low constraints + Builder DNA + Extreme pace = Hot AI Startup
The hardest door to walk through, but positions you for everything afterward
Any constraints + Wannabe Builder = Stay Put
Harsh but true: If you’re not already building on nights/weekends, no job will make you a Builder
Either commit to building on your own or accept being a Manager
The framework doesn’t always tell you what to want. It tells you what’s actually available.
Your Next Move
Stop asking “Should I take this role?”
Start asking:
What are my real constraints? (Be honest, no shame)
Am I truly a Builder or a Manager? (Look at what energizes you)
Which bucket is this company in? (Transform or Scale)
Once you map these honestly, the right door becomes obvious.
In Part II next month, we’ll examine each door in detail—the specific companies, interview processes, and what you’re really signing up for when you walk through.
But first, stop trying to force open doors that were never available to you.
The most common response to this framework: “I wish I’d been honest about my constraints sooner.”
Have your own career question?
Get personalized guidance at Nikhyl.AI— which is where these questions came from. And join Skip Coach to connect with other leaders navigating these same transitions.
