
Stepsero · 2026-05-20 · 17 min
Key moments - from our scoring
Substance score
33 / 100
Five dimensions, 20 points each
Tessa, founder and CEO of HireGains, challenges the pervasive fear narrative around AI replacing knowledge workers by presenting a historically grounded alternative: workers will move up the stack, not out of jobs. She identifies three converging forces reshaping work - remote work normalization from Covid, generational shifts in how Gen Z and Gen Alpha experience work as identity rather than compartmentalized employment, and AI's arrival - that collectively point toward portfolio careers and fractional work models. Rather than viewing AI as a threat to roles, Tessa argues it will eliminate repetitive, transactional tasks (administrative work, paperwork, routine processing), freeing knowledge workers to focus on higher-level problem-solving, innovation, and creative work. She uses doctors' administrative burden as an example: freed from paperwork, they'd spend more time researching and solving complex medical problems. The conversation addresses the legitimate concern that moving up the stack means higher-stakes work, but Tessa emphasizes that this shift creates space for meaningful, purpose-driven work aligned with how younger generations define themselves. Her vision for 2030 involves multiple concurrent projects, democratized skills through AI acceleration, and quick career pivots - not precarity, but flexibility. This episode directly addresses the Anthropic chart and Sam Altman's warnings about AI and knowledge work that have dominated LinkedIn discourse, offering a more nuanced framework for understanding workforce transformation.
Moving up the stack means AI takes over repetitive, transactional work (paperwork, administration, data processing), freeing workers to spend time on higher-level activities like creative problem-solving, innovation, and strategic thinking. A doctor spending less time on administrative tasks could instead research new treatments or solve complex medical problems.
Remote work normalization accelerated by Covid, generational shifts where Gen Z views work as identity rather than compartmentalized employment and demands purpose-driven roles, and the arrival of AI to handle repetitive tasks.
She envisions portfolio careers with multiple concurrent projects and focus areas, more contract and fractional work arrangements rather than permanent full-time hiring, and people switching careers quickly due to democratized skills and AI acceleration of individual impact.
Because throughout history, technological shifts have moved workers up the skill ladder rather than eliminating work entirely - new technologies automate lower-level tasks, creating space for higher-value human work that didn't exist before.
End users passively receive AI tools, while shapers actively work on training and improving AI systems by identifying edge cases and understanding outputs at a business operations level - work that requires human expertise to make AI systems better and safer.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode surfaces a few interesting reframes - the 'messy middle,' the end-user vs. shaper distinction, and fractional portfolio careers - but these are developed only at a surface level with significant filler and repetition across the 17 minutes. The ideas-per-minute ratio is low, and many segments are spent restating the same thesis rather than deepening it.
I see that AI has this brilliant opportunity to take the work that we probably find quite repetitive, quite Transactional and be able to take that off our table
there are two categories of people. The ones who somehow are the end users on the receiving end of AI and the ones that are shaping the way AI will look like in the future
The 'moving up the stack' reframe and the claim that the replacement narrative is 'historically illiterate' hint at contrarian potential, but neither is backed by historical evidence or a rigorous argument; both remain at the level of assertion. The three forces (COVID, Gen Z, AI) and portfolio career thesis are well-worn talking points in the future-of-work discourse.
the replacement narrative has been historically illiterate
fear narrative moves faster and stays around longer than the other stack side of it
Tessa is a practitioner-founder running an AI-in-hiring platform with an active newsletter, giving her relevant domain credibility; however, she is self-described as only ~3 years into AI, no scale metrics or outcomes for HireGains are surfaced, and the forthcoming paper is unverified. Solid mid-tier practitioner, not a scaled operator.
I first got interested in AI probably about three years ago, to be honest, when, when the acceleration came out
You are the founder and CEO of HireGains, a platform that you describe as AI powered, human governed
Almost no concrete data, metrics, named companies, or specific case studies appear in the episode. The doctor-and-paperwork example is entirely hypothetical, and references to the Anthropic chart and Matt Schumer post are name-dropped without any numbers or findings cited. The entire argument rests on abstraction.
imagine if we could have doctors spending less time on paperwork, administration tasks
we had this anthropic chart that has been widely discussed
The host demonstrates genuine preparation (having read a draft paper and the Substack) and lands one substantive pushback - the 'high stakes work only' concern - that briefly enriches the conversation. However, most questions are leading or affirming, and the closing 'good day in 2034' prompt is a generic flourish that yields no new substance.
Is there any concern in your mind? And this is a fairly common concern, but I'm curious about your take that uh, with AI taking care of, let's call it the grunt work, the operational work, the most boring tasks
I think it's a phenomenal perspective. It, it finally sheds some positive light on a topic that many people fear so thank you for that
Computed from the transcript - who did the talking, and the words that came up most.
The dominant narrative around AI and work is built on fear. But is the replacement narrative historically illiterate, and is there a more nuanced argument to make?". Tessa is the founder and CEO of HireGains.ai, an AI-powered platform, and author of the Human Centric AI newsletter on Substack. In this conversation, we explore three converging forces reshaping the future of work: remote work, generational shift, and AI, and what they mean for knowledge workers trying to figure out where they stand. We also get into the idea of moving up the stack, what it means, why the repetitive transactional work AI takes over is actually an opportunity rather than a threat, and what Tessa believes a good day at work looks like in 2030. A rare and genuinely optimistic take on a topic most people approach with anxiety. Our Guest: Tessa James Tessa James, CEO and Founder of HireGains.ai, is a talent strategist at the intersection of psychology, organisational transformation, and human-centred technology.
Transcribed and scored by The B2B Podcast Index.
Speaker A: Tessa, welcome to the stepsetto podcast. Thank you so much for taking the time.
Speaker B: Thanks for having me. Pleasure.
Speaker A: You are the founder and CEO of HireGains, a platform that you describe as AI powered, human governed. You are also the author of Human Centric AI, a newsletter on Substack, which I particularly appreciate. It looks like there's ah, a thing or two you can tell me about AI or I can learn from you about AI. How long have you been in the space?
Speaker B: That's a good question. I think I first got interested in AI probably about three years ago, to be honest, when, when the acceleration came out. I remember jumping into ChatGPT and just suddenly realizing that things had come a very long way very quickly. So that was probably my first exposure to really the opportunity, the advances that have been made. And that that's, I guess what got me thinking on a different path in terms of what could this mean for the areas that I care about and where I could have impact. So I know AI has been around forever, but I think that was probably the defining moment for me in my journey.
Speaker A: I had the privilege of uh, looking at the draft of a paper that you, that you shared with me and that will be, will be released soon. And um, the paper I found, I found super interesting. You touch on several topics that I believe are very hot right now and dare I say misunderstood. In the paper you describe initially three forces that are converging and eventually you lead, um, the narrative towards somehow the future of work. And you're giving a nuanced answer to a big question that is on anybody's mind, which is in a way, what is the future of work going to look like specifically for knowledge workers? Can you elaborate for me a little bit on that and about what is the main message of the paper?
Speaker B: Yeah, I see, uh, I think about a lot of things, I guess in the workforce as a series of patterns and trends of coming together to predict maybe where we're headed. And so that was some of the premise of that paper. But when I look back in terms of some things that have been converging together, uh, I think that really for me is the feels like it all works together in a tangent with one another to help us think about what the future might look like. So one of the big trends, waves that we had in this space in terms of rethinking, redefining how we might think about work was, was Covid. So for me, I've had the experience of sort of working in a remote setup previously and I just. There are all sorts of dynamics in that, which I think for me was eventually going to play out in the workforce anyway, just based on the way that we experience life, the way that we consume information. I just, we were always on a path in that direction, but Covid really accelerated that. I think what happened was we realized that we didn't have to have the same infrastructure that we'd always known around us to get work done and that we could think about this in different ways. So that for me was the big, one of the first big changes that we've seen over the last sort of decade or so. And then of course we've got new generations coming into the workforce and we tend to define those people as almost a set of personality constructs. I think it's far deeper than that. I think it's about the way that people come in and experience their environment, their personal environment, their work environment, the way that they experience day to day life. And I think about Gen Z and even my own kids, the way that they experience coming in. It's a, uh, Technology has blended everything in our lives, right? We don't have a work day and a personal day. And I know that there are some instances where we have that level of distinction, but not typically. And so with that I think Gen Z has really has got a mindset of this is identity. For me, my work is who I am. It's not even a blend, it's just, it's all just one thing. So I want this to be meaningful and there needs to be purpose to this. So I think there is a, uh, there's a, there's a connected piece here where Gen Z is, you know, questioning and pushing and thinking differently about what is work and what do I want to do and how do I want to spend my time. And then of course now we've had AI come in and it's really, it's broken. I talk about it breaking the deal like it broke the deal because the deal was usually you'd have a job, you'd work your job, you would probably stay there for a period of time and then considering another opportunity. And I think the way that things are moving and the speed in which they're moving, that uh, level of stability is not there. So I see this all moving together into a place where I think people will embrace more fractional type work opportunities, where they have more of a portfolio style career. Um, and it just imminently, I think just won't look like it used to from a workforce standpoint. I think we're in some sort of Messy middle part of that at the moment. So that's in a very long winded response to your question. That's, that's what the paper's, that's the premise of the paper and what I'm trying to share across.
Speaker A: One thing that um, struck me about the paper is that you touch indeed on these three forces, but then you mention what, what's on everybody's mind these days, which is, is AI going to replace me? Right. We've had um, on LinkedIn, we've had this anthropic chart that has been widely discussed in from many different angles. Some people were visibly concerned about it. A little earlier than that we had this uh, tweet or post by Matt Schumer about um, about what uh, AI is going to mean for knowledge, uh, workers and white collar jobs. It looks to me you have a much more, dare I say, positive take on the future of work. It's a nuanced take, but uh, it's indeed based on uh, this premise that you gave us. One specific thing that stood out to me is this replacement, uh, narrative. Your take on the fact that the replacement narrative has been historically illiterate. So you describe a stack and you're saying that knowledge workers are actually not being replaced, but they're moving up the stack. May I ask you to expand on that and explain what the stack is? How do you see it from your perspective and what does it mean that humans are actually moving up the stack?
Speaker B: Yeah, so maybe I'll address it in a couple of ways. I think when I look at the narrative that's out there at the moment, it is based on fear. And I think, personally, I think fear narrative moves faster and stays around longer than the other stack side of it. So when you look at what's out there when you read LinkedIn, it's, it's in the newspaper, in the front page of whatever. It's all about what AI is taking and, and moving out. And that's the messaging and that's what keeps people glued because it's a fear. Right? We're going to be replaced. Everything's changing. I see it, I see it differently. So I, I feel that what AI can do and where it's really great at doing things is the consistent transactional work. And so the way I see it is, and I can link this back to kind of an early careers story as well if it's helpful to anchor it somewhere. Uh, but I see that AI has this brilliant opportunity to take the work that we probably find quite repetitive, quite Transactional and be able to take that off our table, off our desk and then be able to help us move up the stack. Meaning let's elevate our thinking. We've got something else here that can do the work that is transactional, repeatable and uh, monotonous, whatever you want to call it. Let's elevate ourselves so that we know that that's where Maybe that was 80% of our time. Now we can delegate that to be 20% of our time. We've got now all of this extra time to think about what else we can do to solve problems, to think creatively, to be innovative. Like if I was to take this into a medical example, imagine if we could have doctors spending less time on paperwork, administration tasks. And yes that might impact some roles, but those roles could be redeployed or rethought of differently in terms of managing some aspects, overseeing what's actually taken the manual sort of repetitive things away. And then we've got doctors who uh, perhaps researching more things in health and medicine or problem solving at a different level because they're not having to be burdened with some of this administrative stuff. So basic example, but that's where my mind is. And I feel that when people can sort of get, get okay with that and get okay with the idea that this can be, they can augment their work and then accelerate what they, what they are doing in their work through AI I think we have a different mindset around all of this and we can stop listening to the fear messaging. We can start sort of moving forward into a positive direction and then everything else I think will, will follow. That's my perhaps delusional view, but I definitely stand by that. I think that's the pattern. And yeah, I'm sort of waiting to see it, see it become a reality.
Speaker A: Is there any concern in your mind? And this is a fairly common concern, but I'm curious about your take that uh, with AI taking care of, let's call it the grunt work, the operational work, the most boring tasks in um, in many fields. What we are left is with high stakes work only, it's of course like it's a negative, it's a negative take on what you are describing. But, but I'm curious whether this has crossed your mind or whether you have any thoughts about that.
Speaker B: You know, I don't have all the answers to that. I get your point because it feels like if you're moving up the stack, maybe you're moving up the risk level or the stakes level as Well, I think there's also like, if I think about early careers and a lot of the news around those roles disappearing and I see that that is actually if you were to look at graduate positions or entry level positions, there is this kind of, kind of period right now. People trying to figure out those are the roles we've always had, they've always looked like that. Now AI can do that. What needs to come next is someone who says, okay, but we've got these amazing people coming into the workforce and their perspective is like this and their lens on life is like that. And so, yeah, we can't replace, we can't put them into those roles because we're, we now have different opportunities. But let's think about the value that they bring into the workforce with the way that they consume life and experience life and that lens and perspective and create new opportunities that help us move forward in different ways. Because at the end of the day, the AI, if we're talking about this from an LLM perspective, it's data, it's information, it's pattern recognition across billions of data points. We still need that nuanced human problem solving, innovation aspect. I don't think we. I know that there's theories out there that AI will get to that point of being able to do all of that. I just, I don't know if that's the case. I think those things that make us innately human will continue and we just have to let the workforce design catch up.
Speaker A: Is it fair to say that in a way there might be a future where people close the gap between what they can do and what energizes them? What they can do and what their purpose is?
Speaker B: Yes. So you mean in terms of is this an opportunity to m, move more in sort of the direction of where you feel pulled versus yeah, absolutely. I mean, that is my nirvana. That is, that is my mission in life. I think to enable people to be able to actually show up and feel like whatever they're getting involved in has some connection into their meaning and purpose. And I think Gen Z and Gen Alpha and I don't know what comes after that. Is it beta? I'm not sure. But, um, I think they will force us to move in that direct. I think that wave is coming no matter what. Because I've got young kids. You just see how they engage in life. It's not. There is no black and white. It's all just. It's one gray and they want to be in it and they want to experience things that are meaningful. To them and purposeful to them. And I think naturally then in the workforce we're going to see people who want variation. They want to make sure that what they're doing is connected to who they are, what they enjoy doing. And so I think there's this very unique opportunity of these two things coming together now in a way that we haven't seen before. And I think that will be how we start to define the workforce.
Speaker A: Tessa, may I touch back on the idea of the messy middle that you, that you mentioned just before you wrote something in your, in your substack that I found very interesting. And it was somehow about human adaptability within this messy middle, ah, phase of, of uh, where AI stands. And you mentioned there are two categories of people. The ones who somehow are the end users on the receiving end of AI and the ones that are shaping the way AI will look like in the future. May I ask you to tell me more about that?
Speaker B: Yeah, I mean, that was very much linked into, um, also work that I see expanding out there, which is where people are like. If you think about our journey with AI, we all jumped into ChatGPT and Claude, and we've all sort of played around with that. And those models have been built based on, um, billions of data points that have been trained offshore, nearshore, in those types of locations. We've now kind of got past the foundations of that. Like that works. We all get it. That is also moving up the stack in terms of. We've now got to a point where we're pushing these types of models into organizations and they're getting deeper into the business operations in terms of systems that people are building in terms of what, how they're working with their customers. And that needs a different level of training. That's not something we can take out and, you know, and sit behind a computer and say, is it a cat, yes or no? Is it, is it, is it black or is it white? It's a new level of um, understanding what the outputs are, what the edge cases are. So there's a whole range of um, opportunities for people to actually get involved in how these systems start to support. But it's very difficult to see at this stage or experience for me, for me to experience at this stage, people recognizing that as an opportunity because there's so much fear messaging out there with people thinking that AI is taking the job, their job, so why would they come in and help it be better? But if we can all help it be better, we can move up the stack and we can have even Better outcomes than what we had imagined before. So it's this process of we need to get into a different mindset around AI, which is difficult because those who are selling AI and these big AI labs and models, it's helpful for them to tell that story of how this is going to take over so much of work. But actually I think the reality is quite different. So I feel like we have an opportunity, I guess in a more macro sense to shape how this moves forward. And so the more that people get involved in doing that, in working with AI, in even training AI, the better we will be in terms of where that trajectory goes.
Speaker A: Such an interesting perspective. So we are heading slowly towards the end of the conversation. There is one, if you will, final question that I have for you. It's um, let's say it's 2034 or five years from now. What does a good day at work look like in your eyes?
Speaker B: So firstly, 2030 is four years away. That's a terrifying. Yes, I would imagine. And maybe this is a little, I'm usually a little bit sort of ambitious with my timelines, but I think we're heading in a direction where people wake up, they have multiple areas and projects and focus points. It's not just they don't sort of have one opportunity to work towards, it's multiple things that they're probably focused in on, all of which provide some level of meaning. I'd imagine that people were switching career paths quite quickly with all of the advancement in AI. It feels to me like skills, knowledge have become quite democratized. So I think there's an opportunity for people to switch careers and focus areas and explore things that maybe they've not been able to explore before. So I feel like in four to five years, if we're not already there, then we're very much on the way for people to have more of a portfolio career. So we'll see less permanent hiring, we'll see more contract contingent, fractional type work playing out where people can lean into their strengths as much as they would like to and be accelerated with AI. So it doesn't feel like eight full time jobs, even though the impacts that you might be having could be sort of at that level. So it's a, it's a very fragmented but sort of purpose focused approach. I would say I probably would work on that wording before I put it, advertise it anywhere. But something, something like that. Yeah.
Speaker A: I think it's a phenomenal perspective. It, it finally sheds some positive light on a topic that many people fear so thank you for that. And, Tessa, thank you so much for taking the time. It's been a pleasure. I hope we can again at some point.
Speaker B: Absolutely. Very welcome. Thanks for having me.
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