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The senior job search in this market is exhausting. Hundreds of applications, months of LinkedIn scroll, the slow attrition of confidence. That part isn’t getting easier. What surprised me, sitting down with three senior product leaders who’d just come through it, was how much else has changed. The playbook is out of date in at least ten ways.

I sat down with Dana Ingraham, now leading agent products at Harvey; Briana Ings, now leading Loom at Atlassian; and Pei-Chin Wang, now founding her own company. (Volume 2 of these “post-mortem” conversations; the first was six weeks back with three different leaders.) The state I heard from all three was something I’ve started calling smiling exhaustion: working hard, going long, and surprised by how good it feels. Joy is not a word I expected to come up in a panel about navigating a tough market. It came up four times in the first half hour.

Below, each one in depth.

1. Joining a New Company Used to Be a Year of Headwinds. Now You Get a Tailwind.

“I’ve been at my current company for years. Starting over and feeling like an imposter again sounds exhausting. Maybe staying is the safer call.”

The first year at a new senior role used to be a slog: no context, imposter feelings, slow ramp. AI tools have replaced the headwind with a tailwind.

The reason starting at a new company is supposed to be brutal isn’t the change itself. It’s the context vacuum. You don’t know the products, the people, the politics, the history, and you walk into rooms where everyone has months or years of background you don’t. Imposter syndrome runs on that gap, and at a new senior role the gap is wide by definition. Most candidates expect six months of feeling slow. Many find it’s closer to a year.

What these three found is that the gap closes faster than that now. Three weeks into Harvey, Dana described her first month as easier than expected, and traced it directly to context. On day one she connected agents to every internal system at Harvey: Slack channels, internal docs, customer records, deal pipeline. That gave her an always-on company expert from her desk. Months of chasing context collapsed into days of asking questions. Briana described the same pattern at Atlassian: when she doesn’t know what an internal acronym means, she types it into an agent instead of hunting down the right person. The dumb-question tax is gone.

That changes the imposter equation. When you can close the context gap before a meeting, vulnerability stops costing you credibility. You can admit what you don’t know, because you have a way to close it fast.

The implication isn’t that you should leave. It’s that if the new role now comes with a tailwind for the first time, the weight you’ve been placing on staying with what you know should drop accordingly.

2. Founding Got Fast, Fun, and Skill-Additive

“Is founding actually a serious option for someone who’s been an employee my whole career?”

Founding has become a viable mid-career option because it’s fast, fun, and skill-additive, even if it doesn’t work out.

Pei-Chin had no founding ambition. She left Modern Animal expecting to take time off and join another company. She founded instead, three weeks ago, with two friends. Her experience surfaces three shifts that have made founding accessible to people who don’t think of themselves as founders.

Speed. Three months from now, she said, they’ll know whether the thing they’re building is real, and if not they pivot quickly. Building a real product with a small team takes weeks, not months. Validation that used to take a year now arrives in a quarter. The bet you’re making when you found is smaller than it was.

Fun. Pei-Chin volunteered this without prompting: she’s having a ton of fun. She doesn’t think she’s been this happy in a long time. The proverbial founder misery hasn’t shown up. The AI-era founder experience, at least in the early going, is meaningfully different from the experience of working inside an established org.

Skill that pays off either way. Founding from zero forces the deepest hands-on use of AI tools that exists. Every day, you’re solving real product problems with the most powerful tools available. If your venture takes off, that fluency is the foundation of the company. If it doesn’t, you come back to senior employment fluent in AI in ways most senior leaders aren’t, and the next role available to you is often better than the one you left.

Stack those three together and founding stops looking like a binary capstone bet. It looks like a fast, fun, skill-compounding option that’s lower-risk on the downside than it used to be. For senior leaders making their next move, it deserves real evaluation, not a polite dismissal.

3. Most AI-first Companies Don't Hire Remote. Some Hot Companies Still Do.

“I live outside SF. Are the hot AI roles actually accessible to me?”

The remote-resistant tier is real, but it’s narrower than the household-name conversation suggests. Hot mature companies that grant remote exist; you have to look past the obvious AI brands to find them.

Plenty of senior people work remotely. Plenty of large companies have remote teams. From the outside, qualified senior candidates should be able to negotiate around location. For some hot companies, they can. For most, they can’t, and the rule gets strictest at the frontier-AI-lab tier: young, SF-concentrated companies where AI is the product. They don’t have remote muscle yet, and they’re not trying to build it.

Briana lives in San Diego. Pei-Chin lives in Seattle. Both knew location would matter. Neither expected it to matter this much. Looking at public big tech roles, Briana cut 80 percent off her list. Strong AI fluency wasn’t enough to bend the remote rule. Before Pei-Chin decided to found, she was looking for roles too: even targeting private companies, she cut 70 percent off hers.

The pattern: the closer a company sits to the frontier-lab archetype, the harder the door is to crack remote. Even very strong candidates struggle to get exceptions there. The ones who do are people with exceptional AI brand or skill. As Briana put it, you’d need to be an “AI guru in the industry” to bend the rule.

If you’re outside a hub, look beyond the obvious AI brands. Hot mature companies that hire remote exist (Atlassian, where Briana now leads Loom, is one). Finding them takes more search effort, but the door is open. Don’t burn the search budget hammering frontier-lab applications hoping for an exception. The AI-guru bar is real. Or seriously consider a move.

Calibrate the remote calculus before you build your pipeline. If you’re outside a hub, you’re not cut off from hot roles. You’re cut off from a specific tier: the frontier labs. The rest of the market, including the subset of mature hot companies that grant remote, is reachable. It’s just less visible than the brand-name list.

4. Don't Filter for AI. Most Growing Companies Are Heading There.

“Should AI exposure be a hard filter for my next role?”

Most growing companies are already going AI, including the established ones. Filter on your other must-haves; the AI exposure comes with.

Briana and Dana both deprioritized “AI company” as a hard filter. The companies they actually wanted (winning on scale, role shape, product quality, leadership) were heading to AI anyway. Harvey is built around AI: the legal product IS the AI. Atlassian is on the same trajectory, with arguably the strongest reason to push hard. Established companies have the most distribution to defend and the most to gain by getting it right. AI is the top strategic priority across Atlassian, and Briana’s team is shaping Loom into that future.

Pei-Chin is the exception that proves the rule. Her non-negotiable was getting closer to the technology itself, building products where AI is the core, not just a layer on top. That’s a more specific ask, and it pulled her toward the narrower set of companies that build AI as the product itself.

If you came into your search assuming AI had to be on your must-have list, recheck the math. The companies winning on what you actually care about (scale, role, team, manager fit) are mostly going there anyway. Filter on those, and the AI exposure comes with.

5. What You’ve Built Has Replaced What You’ve Titled

“How do I get noticed at companies that don’t already know me?”

At every stage of the process, from first contact through interview, what you’ve built and how you talk about it has more weight than brand-name credentials.

Pei-Chin’s experience cracking into AI-native opportunities surprised her: “My credentials didn’t matter. They don’t care that I was a CPO. What have you built?” The title and the tenure didn’t open the conversation. The work she’d shipped did.

The same dynamic shows up at first contact. Dana gets cold outreach almost daily and opens almost none of it. The “congrats on the new role” notes (most of which now smell AI-generated) go in the trash. The exceptions are messages with an HTML file attached: a clickable prototype of a feature the sender thought Harvey should build. The interactive artifact, in her words, is “way more compelling” than any pitch. So few candidates actually do this that the ones who do stand out instantly.

The same dynamic shows up in the interview. Briana came out of hers surprised that “almost every product question was AI related”: model accuracy, the AI stack, eval design. The bar wasn’t memorized AI theory. It was whether she could talk fluently about her own hands-on use of the tools, breaking each question down to first principles she’d already worked through. The candidates who can describe what they’ve built, concretely and in their own words, clear that bar. The ones reciting concepts don’t.

The structural shift: storytelling what you’ve built dominates the conversation now, at every stage. The differentiator isn’t the prototype itself, it’s the specificity of the work and the fluency you bring to talking about it. Spend the time on real building, and on being able to articulate what you did and why it mattered.

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6. Take Any Interview at a Target Company

“What if I’m excited about the company, but not the level?”

At companies you actually want to work for, take the interview anyway. The cream rises to the top.

Briana’s pipeline strategy was unusual. At companies she genuinely wanted to work for, she said yes to any interview, including individual contributor roles. The bet wasn’t that they’d flex on title once they met her. It was that being inside a great company was worth the level reset, and that her work would speak for her over time.

The principle: in a market this turbulent, betting on company quality matters more than protecting your level. If you believe in your own ability and you’re certain about the company, the IC entry point is a reasonable trade. You’d rather spend two years at a top company in a slightly smaller role than two years at a less compelling company at the level you’re protecting. The catch is that this only works with high conviction in the company. Without it, you’re just settling.

For senior leaders facing pipeline scarcity, this converts a “no opening at your level” rejection into a real conversation. The level may take time to recover. The quality of company you’re inside doesn’t.

7. Turn a Non-Traditional Resume Into Leverage

“I haven’t worked in a brand-name company with a well-known product. Doesn’t that put me at a disadvantage?”

The candidate who teaches the interviewer wins the room.

Briana’s experience: “I joined an interview once and the guy was like, ‘I literally don’t know what to ask you. I don’t know how to deal with your resume.’” Most candidates would treat that moment as a problem. Briana treated it as her opening. She walked him through her story, then coached him on what to ask.

The translation move: “The problems I solved at a property management company are similar to the problems you’ve solved here. You just haven’t heard of them.”

When an interviewer doesn’t know how to evaluate you, the room tilts toward whoever has a clear narrative ready. If you walk in knowing how to bridge your background to their problems, you stop performing for someone hunting for the right rubric and start running the conversation. The interviewer sees agency, clarity, and the ability to structure ambiguity in real time. Those are exactly the qualities they’re hiring for in the role.

The principle: when your resume doesn’t fit the pattern, don’t try harder to fit. Take the room. Teach the interviewer how the work you’ve done maps to the work they need. The unfamiliar resume becomes the moment that demonstrates you’re the kind of senior leader who can step into ambiguity and make it productive.

8. Don’t Take an AI Class. Build Something Instead.

“I want to get serious about AI. Should I take a class?”

The models teach you while you use them. Build something you actually want, push the agent when its answer doesn’t quite land, and the fluency compounds in a way that shows up clearly when you talk about AI later.

None of the three took classes. None followed a curriculum. Dana’s journey started with Claude Code. As she put it, she felt like a sorcerer. She was pinging her engineers at Airbnb asking if this was what they always felt like, that they could just build anything they wanted. She built what she wanted personally first: iOS apps for her daughter, travel tools she’d been dreaming about.

Pei-Chin’s first afternoon with Claude Code was an aha moment. The bigger shift was emotional. She started from “I’m behind, I need to catch up” anxiety. Within weeks it had flipped to self-actualization. That joy cycle, she said, was a stronger driver than the anxiety ever was.

The mechanism is simple. The models are good enough now that they teach you while you’re using them. Ask the agent what something means. Ask it to walk you through a concept. Push back when its answer is shallow or you don’t quite follow. Build something concrete (an internal tool, an iOS app, a thing that doesn’t need to ship), and the technical learning happens as a byproduct.

The reason this matters beyond your own development: hands-on engagement with the tools shows up in how you talk about AI. The candidates who’ve actually built things have a fluency that’s impossible to fake, and other senior leaders pick up on it in three minutes of conversation. Reciting concepts you read about feels different. Engineer the joy of building, and the credibility follows.

9. Signal Your Constraints. Watch the Response.

“I have young kids. Do I have to write off the AI-era roles to keep my evenings?”

The 9-9-6 companies get filtered out up front. Inside the rest, what matters is whether your boss internalizes the constraints you signal, not what they say about boundaries in the abstract.

All three of these leaders ruled out 9-9-6 companies up front. None of them were going to take a role where the company-level expectation made boundaries impossible. That part is straightforward. The harder, more consequential filter applied inside the set of remaining companies, where every boss says they support work-life balance.

What separated the offers they took from the ones they didn’t was whether the people they’d report to internalized the constraints, not just acknowledged them. Dana’s test: am I around a lot of parents? Are the founders mature enough to understand what it actually means to have a life outside of work? When she signaled her non-negotiables on day one, she watched whether the response was real (calendar respect, no late-night pings, comfortable rescheduling) or performative (”of course we support balance,” with no behavior change). Briana ran the same test. Both got the real version. Neither hit pushback.

The signals worth reading: do parents on the team actually leave at 5, or are they in Slack at 7? Does the founder have kids and act like it? When you describe a non-negotiable, does the response sound concrete or scripted?

Working hard is fine. Working hard always is not. The boundary is on when the work happens, not whether you’re committed to delivering it. Briana’s hard time blocks are 7 to 8:30 AM and 5 to 7:30 PM; Dana keeps a physical brick device that locks her out of her phone from 5 to 7 PM. Both put in long hours after their kids go down. They’ve chosen which hours are theirs, and they joined teams where that choice was respected without negotiation.

10. Hold Your Identity Loosely

“My professional identity is what I’ve built my career around. How much does it actually need to change?”

The career you’ve identified with and worked years to build is getting reformatted, whether you like it or not. Holding it tight just makes the reformat painful.

Pei-Chin’s parting line: “Everyone’s identity is going to change drastically. Don’t hold it too tight.”

Look at what’s already happened to these three. Dana, the product manager, now owns agent platforms and ships iOS apps herself. Briana, the startup CPO, now leads a division at a far larger company. Pei-Chin, the self-described employee, is a founder. Each shift looked unlikely a year ago. None of them rhyme with each other. What they share is a willingness to let the role of “what I am professionally” reshape under them rather than defending the old version.

The throughline of this conversation isn’t “do what these three did.” Their moves don’t rhyme. What unites them is what they found on the other side: smiling exhaustion. Working hard, going long, and surprised by how good it feels. The moves are softer than they look. The curves are shorter than they feel. And the version of yourself you’ll be in six months may not be the version you’re protecting today.

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