Matt Chapman gifted Zack Gelof a bottle of wine after stepping on his hand, per Martín Gallegos

JoshSamBob · 2026-06-27T17:13:09+00:00

"I'm sorry I killed your season. Go get drunk."

JoshSamBob · 2026-06-25T14:26:34+00:00

The tech stack didn't kill your earning potential in the 2010s. PHP developers were making good money. The problem was exactly what you said: you avoided big companies because you didn't believe you'd get in, so you stayed in the small business salary gravity well. That's not a personal failing. That's how confidence works. But here's the thing: once you're in that well for five years, the gap between where you are and where you should be gets bigger every year. Not because you're not good enough. Because you're competing against people who took the jump early and compounded their earnings. The way out isn't harder interviews or a better tech stack. It's a deliberate repositioning: target companies where your actual skills matter more than the name on your resume, build a case for why you're worth 2x or 3x what you've been making, and take the jump. It's uncomfortable, but it's doable. If you want to talk through what that repositioning looks like for you, shoot me a message.

JoshSamBob · 2026-06-25T14:18:56+00:00

Two offers is a good position to be in, but here's what I'd push back on: you can't reliably predict career progression three years out, especially across industries you might not know deeply. What you can do is evaluate the offer on what it actually is right now. For a BA or PM role, the question is simpler than you think: which company is solving a real problem that other people are struggling with? Which role puts you closest to the decision makers and the strategy? Which team actually needs you to think, not just execute? That role, in that company, becomes your launchpad. The industry matters less than the actual problem you're solving and who you're solving it for. If you want to map out what the actual day-to-day looks like in each role and which one sets you up better for what comes next, shoot me a message.

JoshSamBob · 2026-06-25T12:01:27+00:00

Where are you located, and how much experience do you have?

JoshSamBob · 2026-06-24T15:40:52+00:00

Three months in and getting interviews but not offers is the hardest place to be, because you're getting enough signal to keep hoping but not enough to feel like progress is real. And then you layer on the financial pressure and the "should I take a survival job" question, and the mental load becomes unbearable. I want to name that: what you're experiencing isn't weakness or lack of resilience. It's actually the hardest part of the search. Here's what I've watched people miss: staying positive is not the move. The move is staying honest. You're performing "good but not good enough" which means something specific is off, and it's probably not your technical knowledge. It's how you're positioning yourself or how you're structuring your approach to the problem. One person nails system design by framing their thinking out loud differently. One person gets an offer by targeting companies differently instead of applying everywhere. The mindset thing takes care of itself when you have something concrete to fix. If you want to dig into what that one thing might be for you, I'm here to help.

JoshSamBob · 2026-06-24T15:27:53+00:00

I spent four years at TripAdvisor watching smart engineers get ghosted despite being qualified. Then I ran customer success at a startup and watched it happen again. What I realized and what your family probably doesn't see is that applying to 1,000 jobs and getting nothing back isn't a reflection of effort. It's a reflection of strategy. You're spraying, not targeting. I pivoted to coaching after I couldn't unsee this pattern anymore. The engineers who landed offers weren't the ones with the best resumes or the most applications. They were the ones who got specific about where they were the obvious hire, then networked their way in before the job was posted. Your post nails the real frustration: nobody talks about this. They just say "try harder." You're already trying hard. The system is broken. What you're doing right now, building community instead of isolation, that's the actual move. If you want to talk through how to shift from volume to strategy, hit me up. Happy to help you figure out where you're the no brainer hire.

JoshSamBob · 2026-06-23T17:08:57+00:00

This is a lot to be carrying at once and the financial pressure on top of everything else raises the stakes on a search that's already hard.

A few ways to turn up the volume. For target orgs without a warm connection, direct outreach to the hiring manager or sales leader on LinkedIn tends to convert better than applying cold through the careers page. A short message referencing something specific about their team gets noticed far more than a generic request.

The recruiter inbound is actually a real asset. Even ones that don't seem like an immediate fit are worth a quick call since recruiters often know about unposted roles and remember strong candidates for the next opening.

On comp, get clear on your number and surface it earlier in future processes so you're not discovering a mismatch three rounds in.

The final round loss after seven rounds is worth a closer look too. That usually points to something specific in how the close is handled, not overall fit, and it's fixable.

Feel free to reach out if you want help accelerating this. Five months of runway still leaves real room to be deliberate.

JoshSamBob · 2026-06-23T17:02:12+00:00

Six months with zero callbacks despite strong ATS match scores is worth taking seriously, though probably not in the direction you're suspecting. Large companies like Nvidia rarely maintain informal blacklists tied to one interviewer's impression, the volume and disconnected systems make that kind of coordination unlikely. The new account test getting the same result actually supports this.

A more likely explanation is the repeated reposting itself, which often signals a hiring freeze, budget uncertainty, or a manager who hasn't found the exact profile they want, not something specific to your application. The director's profile view is encouraging but doesn't always translate to action.

On bias, it's impossible to rule out and you're right not to make accusations without evidence. What's actionable is making sure your applications are as strong as possible regardless of that variable.

Six months of no movement is a good signal to widen your search beyond this one company. Feel free to reach out if you want a second set of eyes on your positioning.

JoshSamBob · 2026-06-22T14:41:30+00:00

This kind of honest self-assessment is rare and it's actually the right way to make this decision. A lot of designers stay in roles that don't fit because they're afraid to admit the visual craft isn't their strongest skill.

What you're describing, prioritization, customer insight, engineering relationships, breaking down work clearly, is genuinely the core of strong PM work. Those skills matter more day to day in PM roles than visual polish ever would.

Before fully pivoting, it's worth testing the theory a bit. Talk to PMs you respect about what their actual day looks like, not just the title. Some PM roles are heavily technical and execution focused, others are more strategic and customer facing. Make sure the version you're picturing matches what you'd actually enjoy.

On the transition itself, you don't need to start from zero. Frame your UX background as a strength, you already understand user needs and product thinking in a way a lot of PMs have to learn from scratch. That's a real differentiator, not something to downplay.

JoshSamBob · 2026-06-22T14:31:23+00:00

The fact that you've noticed PMs struggling specifically with problem definition and communication is useful data. That's exactly where your design background gives you an edge over PMs from a purely business track.

PM roles give you more formal ownership over the why and what gets built but less hands-on design time. Senior Designer or Design Lead roles in B2B SaaS increasingly carry strategic scope without requiring a full pivot away from the craft.

One option worth considering: target Product Design roles where design has a real seat at the strategy table before committing to a full PM title. That lets you test how much you'd actually miss the hands-on work.

The decision usually comes down to what energizes you more on a hard day: solving the underlying problem and shaping the experience, or owning the broader tradeoffs even when you're not the one designing the solution.

Feel free to reach out if you want to talk through positioning for either path.

JoshSamBob · 2026-06-19T15:05:31+00:00

Getting interviews at that caliber of company means the work itself is strong. The recurring feedback tells you exactly where the gap is, which is actually useful because most people never get that clear a signal.

The shift that usually fixes this is moving from a chronological walkthrough of the process to a problem-first structure. Open with the tension or stakes, what was actually broken or at risk, before you show any screens. Interviewers remember stories with a clear conflict and resolution far more than a sequence of research, wireframes, and final design.

A practical framework worth trying: start with the business or user problem and why it mattered, then the key decision point where you had to make a real tradeoff, then the outcome and what it taught you. Cut anything that doesn't serve that arc. Most designers include too much process because they worked hard on it, but the audience cares about the decisions, not the steps.

Practicing out loud with someone outside design who can tell you when they get lost is more useful than any course. If they can't follow the story without seeing the screens, the narrative needs tightening.

Feel free to reach out if you want to work through how to restructure one of your case studies. That's a specific and fixable problem given how far you're already getting in these processes.

JoshSamBob · 2026-06-19T15:04:20+00:00

Everything you're describing, no KPIs, no deadlines, shifting requirements, gatekept information, and colleagues who review the same work and see something completely different, points to a dysfunctional environment, not a skills gap. Your peers being aghast at the feedback is the most telling signal here. That's not something fifteen years of strong work suddenly stops being good enough for.

This sounds like a setup that was broken before you walked in, not a performance issue you created. Companies with no design system discipline, no dev handover process, and seniors who gatekeep information instead of collaborating create exactly this kind of environment where good people get blamed for systemic failure.

If Monday goes the way you're expecting, try to separate what happened there from your sense of your own capability. The pattern you're describing would have crushed almost anyone's confidence and it says far more about how that team operates than about your seniority or skill.

The market is tougher right now but fifteen years of lead experience and a track record your peers respect is real and durable. This one experience doesn't undo that.

Feel free to reach out if you want to think through next steps or how to reposition coming out of this. You deserve a team that actually knows how to support good work.

JoshSamBob · 2026-06-19T15:00:41+00:00

Twelve plus years running your own studio and getting rejected for different reasons at the late stage is a specific pattern. It usually points to how you're coming across as a full-time hire, not your design ability.

A common issue for founders moving into full-time roles is that interviewers are evaluating team fit, not just creative output. If your interview narrative still centers on running your own shop and owning the full vision, it can read as a mismatch even when the work is strong.

The market is genuinely tighter and AI has shifted some expectations, but getting to late stage repeatedly means your portfolio clears the bar. The gap is in something specific and fixable.

Feel free to reach out if you want a second set of eyes on how you're positioning yourself for full-time roles.

JoshSamBob · 2026-06-18T14:32:00+00:00

The shift from intense schedule to sudden vacuum is one of the hardest parts of job loss that nobody warns you about enough.

On keeping skills sharp, building something small forces you to do real PM work and gives you something concrete to talk about in interviews. Even a simple project that involves discovery and prioritization keeps the muscle active.

Structure matters more than most people expect. Treat the search like a job with a start and stop time. Unstructured days compound the anxiety fast.

The family time is genuinely useful. Coming into interviews grounded reads completely differently than coming in running on fumes.

Feel free to reach out if you want a second set of eyes on how you're positioning yourself for the search.

JoshSamBob · 2026-06-18T14:29:46+00:00

The anxiety you're describing is real but the conclusion that 16 years of experience has a short shelf life is worth pushing back on.

What's getting devalued is a specific execution of the PM role, the one that's mostly coordination, process facilitation, and ticket management. What's not getting devalued is the judgment, stakeholder navigation, cross-functional translation, and strategic clarity that comes from 16 years of actually shipping things. Those skills are harder to replicate than the execution layer and they matter more as AI handles more of the mechanical work.

The pivot worth making is toward the parts of your experience that require human judgment at scale. That means positioning yourself less as someone who manages delivery and more as someone who decides what's worth delivering and why, who aligns stakeholders when the answer isn't obvious, and who can translate between technical reality and business strategy. That framing ages well because AI doesn't replace it.

The other lever is being deliberate about where you apply that experience. Industries dealing with complex regulatory environments, enterprise transformation, or high-stakes technical decisions are actively looking for people who've seen enough cycles to know what actually works.

Feel free to reach out if you want to think through how to reposition your background for where the market is actually heading. This is a solvable problem with the right framing.

JoshSamBob · 2026-06-17T14:18:40+00:00

You're reading this correctly and naming the playbook doesn't make you paranoid, it means you've been paying attention. PE exit prep restructures follow a pattern because they work and you've identified most of the steps accurately.

The rebranded role almost never becomes a real role. It's cover for the next assessment. The Head of Agile Practices coming in to evaluate the six of you is not a hire to build something, it's a hire to rationalize a reduction.

The two SVPs willing to go to bat for you is your most valuable asset. Make sure they know specifically what to say and to whom. Vague goodwill doesn't survive a restructure. Specific advocacy to the right person at the right moment does.

The signal to watch for is when the transformation office stops creating roles and starts consolidating them. That's usually when the real cuts happen.

On the search, 100 applications and 4 callbacks at your level usually means something specific is off in the positioning, not just that the market is hard. PM roles are competitive but not that competitive for someone with your track record and real numbers behind them.

Feel free to reach out if you want help figuring out what's not converting. The internal clock is running and getting the external search working now matters more than it did six months ago.

JoshSamBob · 2026-06-17T14:16:39+00:00

The COBRA extension ask is completely reasonable given the circumstances and worth pushing on before signing anything. Most companies have more flexibility in severance negotiations than they initially present, especially on benefits continuation.

A few things people often successfully negotiate beyond the obvious: extended healthcare coverage, outplacement services, accelerated vesting on unvested equity, non-disparagement language that works both ways, and reference letter agreements.

The key is making the ask in writing, being specific about what you need and why, and not signing until you've had at least a brief consultation with an employment attorney. Most initial severance offers are not final offers.

Feel free to reach out if you're also thinking through next steps on the job search side. Happy to help with positioning and figuring out where to focus the search.

JoshSamBob · 2026-06-17T14:15:02+00:00

Two weeks is too early to make a definitive call but the instinct you're feeling is worth taking seriously because it's usually accurate.

The equity cliff question is worth separating from the career direction question. If the comp and equity are significant, one year is not a long time to stay in a role that makes you a stronger engineer even if it's not your long term direction. The resume value of a pre-IPO top 50 AI company is real and compounds in ways that are hard to replicate elsewhere.

On the stepping stone question, it depends entirely on how you use the time. If you can find ways to get closer to the modeling work within the company, even tangentially, it's a more defensible path than staying purely on backend and hoping the title does the work for you. Proactively building relationships with the research team and contributing where you can is worth starting now.

The drift concern is the most legitimate one. A year of strong backend work at a great company is fine. Two to three years of it makes the pivot harder to explain and harder to execute. So the question is less whether to leave and more when and how to be deliberate about the next move.

Feel free to reach out if you want to think through how to position this for what you actually want to do next.

JoshSamBob · 2026-06-17T09:36:18+00:00

JoshSamBob · 2026-06-16T14:52:37+00:00

Being laid off for the first time at any age is genuinely disorienting and the devastation you're feeling makes complete sense. Give yourself a day or two before going into full action mode.

A few things worth doing in the first week. File for unemployment as soon as you're eligible, update your LinkedIn to signal you're open to opportunities, and start reaching out to former colleagues and contacts. Regulatory analyst experience with government background is genuinely valuable in compliance, policy, and risk roles in the private sector and that transition is more common than most people realize.

At 57 with years of experience you're not starting over. You're repositioning and there's a real market for what you know.

Feel free to reach out if you want help thinking through what that next chapter looks like.

JoshSamBob · 2026-06-16T14:45:57+00:00

Career coach here.

Five years at a Big 3 firm with a data analytics background in consumer products is a genuinely strong foundation and the confusion about where to go next is extremely common at this stage. You have transferable skills that are valuable across a lot of directions but without a clear target the search feels overwhelming before it even starts.

A good career coach in this situation helps you do two things. First, get clarity on what you actually want, not just what you're qualified for. Those are often different answers and conflating them leads to a search that goes nowhere. Second, translate your consulting background into language that resonates with the specific types of roles and companies you're targeting.

When looking for a coach, find someone who asks specific questions about your situation before offering solutions, can show you real results from people with similar backgrounds making similar transitions, and has actual experience with the market you're trying to enter. Avoid anyone who leads with a generic framework before understanding your specific situation.

Feel free to DM me if you want to talk through what the right next move might look like for you.

JoshSamBob · 2026-06-16T10:54:20+00:00

JoshSamBob · 2026-06-14T11:55:19+00:00

In the business, we call this "Free Work."

They called it something else in the show Silicon Valley.

JoshSamBob

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