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Asana: The Operating System for Human-Agent Teams—Try Now

In the past few weeks, I’ve seen three offers go out to product executives at ten million dollars a year — top jobs at public and late-stage market leaders. Almost nobody gets that number, and that’s not the point. When the top PMs make that kind of money, it brings the whole industry up: the new archetype, the product builder who operates as an executive, is now highly paid and sought after at every tier. The same profile commands two and three times what it did a year ago.

We watched this happen with AI researchers. When a profile gets scarce enough, pay detaches from the old bands entirely. It’s now happening for product leaders — specifically the ones who can build with modern tools and run an executive scope. There aren’t many. Companies have decided the few are worth a bidding war, and the packages look less like salary bands and more like pro-athlete contracts.

For some of you reading this, that tier is reachable if you play your cards right — but it takes different math than the advice you grew up on. I take three or four career calls a week right now, and what I told people six months ago isn’t quite what I tell them today, especially with the demand we’re seeing for the elite. So this week’s podcast works through three of those conversations: a leader worried the AI bubble will pop, playing it safer than she needs to. A consultant trying to become a product builder, struggling to find the right lane. And an elite executive trying to match joy, purpose, and unparalleled income in one role.

The points below are the highlights. The episode is where the real work happens — three decisions walked end to end, because the moves you make today are what open a path to elite a few years from now.

1. Everyone trying to maximize their career should ask three questions.

2. If you believe you could be elite one day, play the long game. A strong IC or director package in Silicon Valley runs $400K to $1M a year. The elite tier pays ten to twenty times that — so much more that maximizing your current job becomes the wrong goal. Spend less energy on any single offer’s comp delta and more on making sure your current and next roles set up the eventual elite executive seat, if you can make the constraints and skills work. That’s the long game this show is named for: keep your eye on the skip job, not just today’s title and salary.

3. Constraints are a risk budget. Spend it while you have it. One of the three cases is a leader in the Bay Area — no kids, elite potential — who walked away from a hot AI company because the valuation scared her, then found herself choosing between two safe, incremental roles. At her constraint level, the hot AI company was the no-brainer she talked herself out of: even if the equity ends up worth nothing, the skills and the peer group move her forward. If your constraints are low, take the risk now. And if they’re real — kids at home, income constraints, location restrictions — those are inputs to the math, not something to be ashamed of.

4. Staying current beats the biggest job at the best company. The biggest job at the best brand is the traditional advice, and it used to work: for most of a career, the VP seat at a Fortune 20 was the destination you climbed toward. Today that same seat can lock you out of the best companies down the road. The next generation of employers will be looking for people who led a transformation, or shifted comfortably into the new way of working — and that isn’t the brand you bank at the largest companies. The better target is the biggest job at the most current company that will have you. You can test for current from the outside. Ask what meetings are for: moving information — which AI is eating — or making decisions. Ask whether promotions go to people with ideas or people with influence. Talk to teams at Stripe, Meta, or Anthropic and they’ll tell you products are built violently differently than they were twelve months ago.

5. Everyone says they’re a builder now. Verify the market sees you that way. Which PM isn’t building something with AI tools this year? The label costs nothing, so it proves nothing. Put yourself up for internal projects that demand hands-on work with the latest tools, or apply to a few real roles at genuinely current companies, and watch what happens — who shows interest, where they slot you. If the answer stings, better to find out now than four years into a plan that needed the market to see you differently. Either way, the data should tune where your hours go.

6. Assume pay like this comes with strings. It’s hard to believe one seat pays top of market and grows your skills and gives you joy and respects your boundaries — so stop optimizing for all four in one role. If one is lopsided, like pay, assume another is probably missing. Getting paid is still a legitimate goal: last month I wrote about an exec who needed permission not to chase the paycheck. In this episode, the right call for one executive is the opposite — stop hunting for the role she’d love, run the auction, and let the job fund the founding journey that comes after. Same math, different inputs. Sequence the traits you used to maximize all at once. You can have it all — just not at the same time.

If there’s a thread across the three cases, it’s that the same situation produces different answers for different people. Your relationship with money, your abilities, your appetite for risk — they change the math. I’d be suspicious of anyone selling a formula for this market, including me. That’s why we run these episodes as case studies: the factors surface one at a time, the trade-offs get debated out loud, and you can pattern your own situation against someone real.

The full conversations are on the podcast — come hear how each one plays out.

Have your own career question? Get personalized guidance at Nikhyl.AI. It’s where the questions keep coming, and where I’ll keep sharing what I’m learning.