Founder's Story - Why Great Hires Fail and How to Fix Talent Market Fit | Ep. 327 with Deepali Vyas of Founder & CEO, Vyas Media & 'The Elite Recruiter'

Episode Date: March 24, 2026

Daniel Robbins interviews Deepali Vyas about the real reasons people get put on performance improvement plans, how founders can diagnose misalignment before it becomes a firing decision, and how CEO and C-suite profiles must evolve as companies scale. Deepali shares behind-the-scenes insight into executive hiring dynamics, including the power networks that shape boards and why women founders can face different patterns of removal. The episode closes with a clear view of what’s next: portfolio careers, fractional expertise, and a workforce increasingly driven by leverage, skill, and distribution. Key Discussion Points Deepali reframes PIPs as a symptom of misalignment: wrong role, wrong stage, wrong manager, or wrong pressure profile, and argues the real leadership question is “where would this person win.” She defines “talent market fit” as the match between a person’s wiring and the company’s current stage and constraints, and warns founders to ask, “did the person make the logo or did the logo make the person.” Deepali explains how CEO needs evolve at inflection points, using the Uber search as an example of needing institutional process and maturity once a company outgrows founder-led chaos. On AI, she lays out level one, level two, level three adoption and says most companies are missing level two, the workflow layer where the real ROI lives, which is why layoffs get justified as “AI” while productivity gains lag. She predicts the rise of the portfolio career: high-skill talent stacking experience, then shifting into fractional advisory, consulting collectives, and multi-income expertise that disrupts traditional firms. Takeaways Performance is contextual, and “fire fast” is often the wrong move; diagnose capability, energy fit, autonomy fit, and stage fit before assuming someone is the problem. Hiring the “best” résumé is risky if the environment that created their success is not the environment you have, so founders must interview for pressure profile, ambiguity tolerance, and stage readiness. The VC and board power dynamic still shapes outcomes, especially for women founders, and structural change requires more women check writers and support beyond seed into Series A and later stages. The future of work is shifting from survival and status to optionality and identity, and the winning model becomes leverage plus skill plus distribution, not tenure. Closing Thoughts This Founder’s Story conversation turns hiring and “future of work” from buzzwords into a practical operating system for founders. Deepali Vyas leaves listeners with a clear message: build teams for fit, not prestige, and design organizations for the reality of how talent wants to work now, not how it worked ten years ago. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

So DiPali, when I was in my corporate environment, what I noticed was people were getting fired. And many times it was because they were not the right fit for the position. But the corporation is like put them on a performance improvement plan. The amazing PIP put them on that. And then basically get them out like whatever, hire, slow, fire fast, right? That was like, you know, do these things. And what I always found is as a leader, as I continued to move up, that people were just not in the right position and they're forced to doing a job that did not fit for them. How do you see this?

First of all, I think this happens more often than you think. And that seems to be the age old problem around organizational design, right? When you see people on PIPs, it's not because they were incapable. It's because they were misaligned, right? It was the wrong role, wrong stage, wrong misaligned. manager, wrong pressure profile. But I think the uncomfortable truth is that, you know, it's sometimes it's not fire fast. It's diagnosed correctly. So I think the corporate mistake here is corporations assume if someone isn't performing in this role, they're underperforming as a person.

And that's flawed thinking, right? Performance is contextual. And so if a person has high potential, but they're in the wrong function, that's a problem. If they're strategic in an execution heavy role, also a problem. If they're executional in a strategic role, also a problem. So they're never going to win. So I think the leadership question here is, why are they failing? And where would this person win? And that's fundamentally different leadership posture.

And I think that there's a diagnostic for this, right? Before you PIP someone, figure out what is their capability? Like, do they actually have a skill set that's required? Not from before, but like, what are they really, really good at? And then where's the energy fit? Where does this work drain them versus what energizes them? If someone who would have asked me that early on in my career, Dan, it would have been super obvious where I thrive versus where I am. I suck at details. Period. Full stop. I suck at it. But I am really good at empowering people, setting big vision, energizing people, a really big goal. And if they would have seen that early on, they wouldn't have put me in, you know, spreadsheet land, right? Because that's not where I thrive. And then the last part is, you know, well, I talked about autonomy fit, but like the stage fit, right? Like, is the company in a phase that matches their wiring, right? Because sometimes you can be in a high growth company and

you're the kind of person that's like, look, I want to be really pragmatic and methodical and whatever, you don't fit there because they want to move fast and break things, right? And so that's where all of these things kind of go wrong and the wires get super crossed. Which leads me to this thought around most founders are obsessing over product market fit. You argue about talent market fit. How do you recognize this before you even put someone in a position? So if you're going to interview so on and you're going to mask them to a position. And then what do you do the moment they're in there if you're realizing it might not be that fit? So founders do obsess with product market fit, which is fair, right? But most of them don't think about the talent market fit. And that's why a lot of

these great hires fail. So what does talent market fit, right? It's not the impressive resume, the big brand logo, the years of experience, the raw intelligence. It's really the alignment between a person's wiring and the company's current stage and the pressure and the market reality. That's talent market fit to be really, really clear, right? So here's where founders, I feel, go wrong. They will hire the quote-unquote best candidate, the most experienced operator, the person who crushed it at a bigger company, but they forget that the environment changed the outcome, right? So I always say this a lot. You can come from a really big branded logo. You really have to ask yourself, as a founder hiring that person, did that person, you know, make the logo or did the logo make the

person, right? That's a really big difference because could they stand up on their own without the logo? And does that matter for you now? Right. So like a VP who thrived in a 3,000 person infrastructure, They had a deep bench. They had clear process. They had brand gravity. Those people will typically fail in a 40-person chaos, right? Ambiguous strategy. Founder-led decision-making.

Capital constraints. Like, that VP is smart. They're different. There's different results that they have in that organization, not in this organization. So we had a guest on before, Francis Fry, a Harvard professor, and she helped the transformation through Uber when it was the founder to the new CEO. And I was fascinated to hear about this whole like founder CEO when the company skills, you now need a new CEO because of the fits of the company.

What do you see around C-suite fit as the company scales over time? So I have a confession. my team and I, my team actually worked on the Uber CEO search. So life has come full circle to talk about it. It was really difficult. And where Uber was at the time, because it was founder-led, if you think about where they were going at the inflection point that they were, and you know, Francis probably can, you know, go more deeply into this, they needed institutional gravity.

They needed institutional process. And Dara was one of the few people that had built several companies to a stage that had these institutional processes that could really build world class frameworks and process and get everybody organized to row in in a in one direction, right? And he had done that over and over again. He also had a bit of gray hair. And he also had the maturity. And he also had the longer term vision because he had been a visionary previously, right? Not to take anything away from from Travis. But I would say that there is an inflection point that happens. And by the way, like, not even just Uber, you know, I'm sure you've watched shows like Silicon Valley, right? And so when those things do ring true in real life, right?

The CEO profile has to evolve based on the stage that the company is at, right? And so I just gave you the sort of microcosm version of a VP that thrives in these types of environments won't really thrive in that. The reverse is also true, right? If you have just played sort of of quote unquote small ball and you really need to go to this level. What does all of that infrastructure need in order to get to that level and you need the right CEO profile? So that's what we're really talking about. It's fascinating. It's very fascinating around what happens with your company as you continue to grow. And also like where would I want my company to even go? And what do I need to sacrifice as a founder? I know many that were kicked out of their company or the board

or whoever investors remove them and put somebody else in. It's very interesting around what happens with the people as a company grows. But let's say there's a organization maybe less than 20 people. They're not thinking about people so much because they're still thinking about growing and scaling the organization. Is there a simple audit or something that they can do to look at their organization to see if the people they do have are correct? The audit, I would say like, if you think about it from like a board level, because that's typically why these things, you know, come about. What stage are we actually in, right? Like not what stage we're aspiring to be, but what stage are we actually in?

What problems dominate this stage? Is it innovation, scale, governance, turn around? What is it? Right. And then do the leaders in our organization, right, whether it's, you know, at this small stage, but they're all basically leaders, right? does that pattern history match that pressure, right? So does past patterns predict future behavior? And can they handle it? That's the diagnostic. And the hard truth is like, you know, sometimes the most dangerous CEO is not a weak one. It's the almost right one, right? And so that's where, you know,

boards and the leadership teams really have to take audit or take stock of where they are. By the way, like you mentioned something earlier, I'm literally working. with the founder right now that got pushed out by a board, even though they had had multiple exits, you know, had 300 million in revenue in their previous companies, but she got replaced by a man, and there was a whole dynamic there as well. And there was a reason for that,

because when they were raising the next level of capital, they needed the face that was going to represent what that next face what that next phase was going to be. So there's a lot of dynamics that get played out in the boardroom. We just had another guest on who was talking about this issue around many times women founders seem to be removed from their company without them. And I've I've talked to some really well-known companies before, not on this show, just privately, who if I said their names, people would know them, like household names. They were all removed from their companies. It's great. There's a whole group of women that meet up, I guess, who have all been removed to talk about, like, what you can do in the future.

Why do you think this is happening? And is it related to what you were just saying around the future of the company? Is it only is it because there's not a lot of women who are founding, you know, larger companies? What do you think it is? So I think that there's a, it's, first of all, I don't think it's random, right? High profile founder removals have happened to men and women. But the pattern feels different for women. And there's actually sort of structural reasons that I believe, right? One is the capital dynamic. Venture capital is still overwhelmingly male. That's a fact.

Boards are still overwhelmingly male, also a fact. And power networks are still relationship-based. So the tension kind of arises where there's founder vision, board pressure, and growth expectations. And the person with less embedded power losses, that's where, you know, there's where, you the conversation takes place and women founders statistically raise less capital have fewer deeply embedded board allies and they get scrutinized earlier for leadership maturity and that compounds under stress my mind i'm blown my mind is blown like i never the power dynamic i never i've never even

heard of this to be honest like the power dynamics of what's going this is why i never raised money because i was too afraid of of the power, giving up the power. And I'm a three-time founder, and I have raised money, and it is a slog in the mud. And I do realize I'm a female founder, right? By the way, in my seat raising money, and I raised over a million dollars for my last, for my last venture, even just that, by the way, the zero to million is the hardest, I would say. I was scrutinized like a series A company versus a seed company as a female founder. That's firsthand experience. Hope it changes because I know.

The amount of money going to women is very small. We just had the previous founder of TaskRabbit who started her own VC firm now to hopefully, you know, try and solve this. But obviously it's something huge. When you look at the future of what the, workplace will be. A couple of years ago, this was like the topic everywhere. Well, people go back to the office, hybrid. Then all of a sudden, they became a topic again. And there was a company recently just laid off 4,000 people and said it was because of AI. I'm sure it wasn't because of just AI. But this is really becoming a thing, right? Like a lot of jobs are being lost to AI. And I have a family

member who is always never had a problem getting a job it just took her like two years to get a job and she's like in a very specific niche job that normally she never has a time without a job so how do you see the future of how this is going to play out with obviously AI and robotics just advancing so fast so I live in the world of data and AI from a search executive search perspective so you know a lot of times even I get a lot of pushbacksing. You know, you're the reason why all of this stuff is happening. You're putting these AI officers in these seats and all of the stuff. I think, first of all, I know the company that you're talking about. When companies say that they laid off 4,000 people because of AI, it's almost never purely AI. But let me tell you what's happening in this market

because I did a video about this recently and kind of connecting the dots here. There's a few things. at the leadership level, AI is being discussed at nauseam. I also think a lot of people don't understand AI in depth. There's a lot of low-hanging fruit, which most CEOs and boards want to take advantage of, but they don't know how. So I call this sort of level one, level two, level three thinking. Level one is have your employees experiment with this stuff, whether it's chat, whether it's, you know, Gemini, whether it's clawed, whatever it is.

When you're doing it individually, you are now maybe 20, 30% more productive because you're using these things with that amount of utility. Level two is when you think about the workflows in your organization of, hey, my team has to deliver this. So there's a lot of different people in a lot of different places in these workflows that really need to connect the dots via AI enablement to actually get that thing in a place where it is, saves 30, 40 percent more time or cost savings or whatever it is. That is the layer that really needs to be built out in corporate America, right? And the third layer is the whole

system redesign. What companies are making a mistake right now is there's level one and then there's level three, but the missing middle is where the ROI is really at. And that's why there's frustration. And that's why you're seeing this overcutting, right? You're seeing all these layoffs saying, well, where's every, EA's going to solve everything, but they haven't done layer two. So they think they're just going to redesign stuff. And I guarantee the people that overcut now will overhire again in the next sort of pendulum swing. So I think that there's a bit of a somewhat of a misinferral misinformation and myths out there. And then, you know, MIT came out with the study saying, you know, 95% of companies are not getting the ROI on AI. But when you dig in a layer deeper, it's because

there's 12 power users of Microsoft co-pilot and nobody else in that organization because they haven't really been taught how to do all of these things. Right. So that's the reality. And that's why I did that video on like, these things will only move as fast as as budgets can approve, right? Or, you know, roadmaps can be approved. And that's going to be a longer cycle. Now, Block did this, you know, layoff. And I think that it wasn't purely about it, but they're taking advantage of the time where, you know, there's sort of cheap capital that's disappearing, there's margin pressure, whatever it is, but they want to signal that they are AI accelerating. I thought of a funny show. We, we as humans give all of everything, all our jobs to AI and robots. Then the robots become

human, they unionize, then they want days off, they only want to work 20 hours a week, and then humans have to take back over. I think that might be what's going to happen. When you, which leads me into, I'm seeing a lot of younger people, let's say in their 20s, taking on jobs at like Claude, for example, who just gave out like billions or hundreds of millions of dollars in stock options to their employees, private options. You could work out like SpaceX and get private options and then it goes public, I wonder how in the next two or three years, they will become multi, multi-millionaires. Some of these companies, I'm seeing like, if you're getting stock like this and it goes public, or even it already is public, or they're getting paid

$500,000 to work at Meta, I wonder if they're only going to work for a few years and then stop working. So that's a great point. And a lot of the stuff that I talk about, you know, on my sort of elite recruiter platform when I'm out there is the rise of the portfolio career. I think the traditional career staying at one company for a very long time is over. And I think the future of work is going to be everyone is sort of stacking skills within these organizations, getting a lot of, you know, compensation for it. But I think that they are going to learn and do all of these things and then say, hey, if I can do it here, I can do it across the board.

And so they will stand up multiple income streams based on their expertise. And that's what a portfolio career looks like, where they will eventually become independent consultants. But now the rise of independent consultants and being able to advise or do sprint work or do advisory work or do fractional work with multiple companies because those companies need that expertise from these very few people, I think you're going to see a rise in the ultimate portfolio career. So it's sort of like single consulting houses, solopreneurs, or they will get their friends together and build this whole consulting collective that goes against all of the big professional services companies that we see today and break those models in half. The big firms need to watch out. It makes sense. I'm also wondering, because we've been talking with other guests around the wealth transfer. I keep thinking about this.

So it's like $80 trillion in wealth in the U.S. that's transferring from baby boomers to Gen Z and millennial in the next few years as they age out. They're getting these jobs that could be making a potentially lot of money. If they can take a few hundred thousand dollars home in dividends, I don't know if they want to work because I, you know, like they, it seems like they're, they want to work for, they want to be passionate workers. They want to travel. They want to dance on.

TikTok or they want to be content creators. I don't know if they want to hustle and grind. I'd say like older millennials enough, we were, you know, you and I, like, we got a hustle, we got to grind. But if I'm making $200,000 a year and just from dividends or $250, I'm not sure if I'm one of them, if I'm going to work anymore, which I wonder what happens to that base of probably highly educated, skilled workers, they are just gone. What do you think?

First of all, you are kind to lump me into older millennial because I'm definitely not that. I am much older than you, but I appreciate that. You know, Dan, that's such an honest question and it's layered, right? Because what you're really asking is if people don't have to work, will they still choose to work? And that happens to a talent and what happens to that sort of talent base, like you said, highly educated. So let's kind of break this down. I think the dividend delusion, right? First, the number of people truly living off of 200,000 passive income is still relatively small.

And I know that those numbers are like really highlighted. It's still relatively small when you think about like the distribution of it. So here's what social media sort of amplifies. They amplify the crypto wins, the exit liquidity, the creator revenue spikes, the dividend screenshots, all that. But statistically, I think most people do not have permanent sustainable passive income at that level, right? There's a loud minority effect that's happening there. Let's be really real.

And I think that work motivation is shifting. It's not disappearing. So like older millennials and Gen X, right? We work from the point of view of like, we need to survive. We need security. We need status, right? The younger cohorts, work is sort of optional identity expression. Right. It's economic context. So if you grew up during 08 and you were watching layoffs and you see loyalty unrewarded, you're going to equate optionality with safety, meaning I'm not going to work for that one employer that can lay me off one day or go under, right? And I think if someone truly has $200,000 in passive income, here's the interesting part. I think those people will build that passive income. They do have ambition. They understand leverage. They enjoy building.

They like status. They like influence, right? None of that stuff is going to disappear. They're going to pivot and they're going to become angel investors. They're going to become fractional advisors. They're going to become creators. They're going to become portfolio operators. They're going to become board members, consultants, whatever.

They may not grind 80 hours, but they're not going to vanish from productivity. And I think this is where I feel, look at me, right? I don't need to work if I don't really want to. I'm doing it out of the sheer sort of passion that I have for it. So I think even this younger audience, this younger sort of cohort that's coming up, they're going to want to do meaningful work. And that might not yield like the comp that we might be used to, but they're okay with that because they have this passive, you know, income back there.

And that's where it's going to win. The new equation I'm going to say is income is really leverage plus skill plus distribution. I think that's the equation. I've never, I think I've talked to over 1,400 people in six years. I've never heard this before. I like to have a guest on who's telling me something I've never heard before. And really, my mind is suddenly expanded. Like, that is very interesting.

I could see this whole like, it's like the rise of the gig economy, like the fractional type. Like, I don't want to work full time for one job. which I don't blame anyone. I remember the last job that I had and I was miserable. And they would never really allow me, even though they kept promoting me. But every time they promoted me, I was even more miserable than the previous time.

And it was like the only option I had. Like I wanted to move somewhere. So I had to get into it. Like I would rather like, okay, I work here for a few months. I work there for a few months. I do this.

I work five different places. for like three hours a week. But damn, that's a structural thing, right? Because corporations are not allowing that type of flow. Exactly. If they were to allow that type of flow in and out and not be burdened by, you know, if, again, if you, let's zoom out 30,000 feet. For that to happen, for your lifestyle that you just described to happen,

you need to make sure that, you know, you have some benefits in the background. You have, you know, something that you have sort of a savings account, et cetera, et cetera, but you have freedom to move through the system. And until we get there, that's a structural problem. However, I think we as the employee base or the solopreneur base or whatever it is, when we start disrupting the system this way that like, hey, we're not going to do this. We're going to do it on a 1099. We're going to do it on a three-month contract.

And we're going to be in and out. And, you know, I will find a way a marketplace that's going to have all my benefits and help me with my quote unquote 401k or an equivalent thereof, I feel very good about being in and out. Most people feel stuck because they don't have the understanding of what optionality looks like. I feel like people and corporations need your help. Yeah, that's what I mean.

That's what it seems like to me. So if they want to get in touch with you because they all need to, how can they do so? So they can reach me. I have my website, depolyvias.com. I'm on Instagram and TikTok and LinkedIn and all of the things. But hello at de polyvias.com. They can reach me there. And then your book will come out eventually.

We'll have to read that. The fact that you're wearing Vias Media sweater, like I need to get a sweater. This has been great. I appreciate it. I've learned a lot. I learned a lot. Thank you. I learned a lot today and a lot of sound bites.

So I can't wait to share this with everyone. So thank you for joining us. Appreciate it.