Welcome to Issue 01 of the People and Progress Report. I've been threatening to write this newsletter for longer than I care to admit, so here we are.
I spend my days advising HR Tech and Work Tech companies, coaching founders and CHROs, speaking at conferences, and building alongside some of the most interesting early-stage companies in the space. I have opinions. Lots of them. And after years of saving those opinions for client calls, board rooms, and the occasional panel where someone hands me a mic, I decided it was time to put them somewhere people could actually find them.
This is not a newsletter full of things you already know, dressed up in buzzwords to sound fresh. This is real talk about where work is going, what's working, what is absolutely not working, and what we should all be doing differently. From someone who has lived every chapter of it.
— Kristy McCann Flynn, CEO & Founder, 127 Ventures
Where I'm Spending My Time
Three bets.
One very clear thesis.
People ask how I manage to operate across multiple engagements at once. The honest answer is that I don't think of them as separate things. Every company I'm advising, investing in, or building alongside is an expression of the same belief: the gap between how organizations say they value their people and how they actually operate is one of the biggest, most solvable problems in business right now. That's the through line. Everything else is details.
127 Ventures: CEO & Founder
127 Ventures is where I bring 25+ years of founder, CHRO, and executive coaching experience directly to the companies and leaders who need it most. I advise and invest in HR Tech, Work Tech, and Ed Tech companies, help them build sharper GTM strategies, get their product story right, and design the people infrastructure that actually supports growth rather than slowing it down.
I also work directly with founders, CHROs, and senior leaders through executive coaching and keynote speaking. The name is intentional: 127 is the number of hours in a week that are not the standard 40-hour work week. It's a reminder that work is not the whole of a person's life, and the best organizations I've been part of are built with that truth in mind.
Current portfolio: Relate, Granted, RallyBright, and soon to be Previ.
Relate: Advisor & Chief HR Evangelist/Voice of Customer
Relate is the most interesting product I'm involved with right now, and I say that having spent 25 years evaluating HR Tech from every possible angle as a buyer, builder, and even investor. Relate is an AI-native trust intelligence platform that measures what actually builds or breaks relationships in real time, from every meeting, with zero surveys.
Through Sandi, their AI coaching layer, teams get post-meeting intelligence on the behavioral patterns that predict whether a deal closes, whether a team member is quietly checking out, and whether a manager is building or eroding the culture they claim to care about. This replaces the engagement survey model that has, in my experience, consistently produced beautiful data and very little actual change.
The seed round is open right now. If you're an investor who believes trust is the most undervalued asset in business, I want to introduce you to the founders.
Granted: Strategic Advisor
Granted is solving a problem that nobody talks about loudly but everyone in HR quietly knows is true: workforce development funding is a disaster to navigate, and billions of dollars in government programs, employer levies, and foundation grants never reach the workers and companies who need them because the process of finding, applying for, and managing that funding is complicated enough that most organizations give up before they even get started.
My role is shaping the go-to-market strategy and keeping the product focused on the right end user. The workers. Not the compliance team.
"The future of work will be defined by the companies willing to ask hard questions about what they actually owe the people who show up for them every day."
— Kristy McCann Flynn
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The Hard Conversation
AI and people at work.
Problems first. Solutions second.
I want to start with what I actually see happening, not the version that sounds good on a conference stage.
This month Anthropic released a labor market report built on real Claude usage data across enterprise customers showing that for white-collar occupations like coding, financial management, and market research, theoretical AI exposure runs close to 94%. Actual current adoption on those tasks is around 30%. That gap gets read as reassuring. I read it as a runway that is getting shorter every quarter, and most organizations are still standing at the gate with no boarding pass.
41%……of employers globally plan to reduce headcount in the next five years due to AI
(WEF Future of Jobs, 2025)
14%……of CEOs have a credible workforce transition plan as AI scales
(Deloitte, 2025)
41% planning reductions. 14% with an actual plan for the people affected. That gap is where the real crisis is forming, not in some dramatic collapse, but in a slow accumulation of anxiety, broken trust, and workers who feel like they're riding a train where nobody's announcing the stops.
What I See Going Wrong
Companies are moving at the speed of competitive advantage and treating the human cost as a footnote. Most AI rollouts are efficiency plays dressed up as transformation narratives. The question actually being asked is "how do we do more with fewer people," but it is almost never said that plainly, and it is almost never paired with an honest conversation with the people whose jobs are changing.
The productivity gains are real. What happens to them is not a settled question. When AI makes a knowledge worker 30% more productive, that 30% typically flows back to the organization's margin. The worker gets the same paycheck and a faster pace. This is a collective action problem, and very few people with actual power are willing to name it out loud.
Using "AI will create new jobs" as a reason not to act today is one of the most convenient things I hear from leadership teams. It may well be true over time, at an aggregate level, in a way that shows up nicely in economic research. That is cold comfort to the 47-year-old benefits analyst in Cincinnati whose role is gone this year, not in five years. Systemic outcomes do not cancel individual accountability.
We are layering AI on top of management practices that were already broken (ARGH!!!!). If your managers cannot give direct, useful feedback without an AI-assisted tool, AI-assisted feedback is not going to fix that. It is going to automate mediocrity at scale. Technology amplifies what is already there. Before you deploy anything, you should be asking: what are we actually building on top of?
None of this means AI is bad for work. I believe it can be genuinely transformative for people and organizations when it is deployed thoughtfully. But getting there requires something most organizations refuse to do: slow down long enough to ask whether the way they are deploying AI is actually consistent with the kind of company they say they want to be. That is not a technology question. That is a values question.
Jamie Dimon said this week he thinks AI will eventually get us to a 3.5-day work week and told Gen Z that emotional intelligence is more important than ever. He also said AI will "definitely eliminate some jobs" and that businesses and governments need to work together before that happens. I agree with all of it. What I do not see is many organizations actually doing that work, because doing it requires having conversations that are genuinely uncomfortable, and most leadership teams would rather send a well-crafted all-hands email and call it a change management strategy.
What Good Looks Like
Say what you are actually doing, before you do it. Tell your people what is being automated, what it means for their roles, and what the company is prepared to do about it. Uncertainty corrodes trust faster than bad news does. Clarity, even when the answer is hard, is what good leadership looks like.
Fund the transition at the same level you're funding the technology. Every dollar going toward AI infrastructure needs a proportionate investment in reskilling, repositioning, and supporting the people whose work is changing because of it. The ratio at most companies right now is embarrassingly out of balance, and workers notice.
Measure what AI is actually doing to your culture, not just your output. Track trust levels, manager effectiveness, and how people are actually experiencing the pace of change. If you are still relying on an annual engagement survey to catch these things, you are getting data about how people felt six months ago and calling it insight.
Bring people into the design process before you build the rollout plan. The most successful AI transitions I have been part of or observed directly involve the people most affected in the actual design of how the change gets implemented. Not as a rubber-stamp exercise. As real co-design. It produces better outcomes and it is the right thing to do, which should be reason enough on its own. This is how you enact change management FYI.
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What I am Reading that I think is What's Worth Your Time
Hot reads from the last 30 days.
With opinions attached.
There is a lot of content about the future of work. Most of it recycles the same three ideas with different fonts. Here is what I have actually been reading this month, and what I think about it.
01 Report · March 2026 · Anthropic
Labor Market Impacts of AI: A New Measure and Early Evidence
Anthropic published its first major labor market report this month, built on actual Claude usage data across enterprise customers. The headline finding: for occupations like coding, financial management, and market research, theoretical AI exposure is close to 94%. Actual current adoption on those tasks sits around 30%. Fortune covered it well this week if you want the readable version before the primary source.
My hot take - What gets buried is the adoption pattern: concentrated in a small set of tasks within a small set of occupations. The disruption is uneven right now. The direction of travel is not. If you lead a people function and this is not on your leadership team's reading list, that is a gap worth closing before someone else closes it for you.
02 Opinion · April 9, 2026 · City & State NY
Corporate America Needs to Come Clean About AI's Impact on Jobs
The New York State Comptroller is calling on companies in the state pension fund portfolio, including Amazon, Salesforce, and Meta, to disclose what AI is actually doing to their workforce. His argument: investors cannot evaluate a company's long-term health without knowing whether AI-driven headcount reductions reflect thoughtful strategy or short-term cost-cutting dressed up as innovation. The SEC's Investor Advisory Committee already voted in December 2025 to recommend mandatory disclosure of AI's workforce impact.
My hot take - This is one of the most important governance pieces I've read this year. Transparency is not an obstacle to innovation. It is what responsible leadership looks like. The companies resisting this disclosure conversation are not protecting their strategy. They are protecting a story, and those things are very different.
03 News · April 6, 2026 · Fortune
Jamie Dimon Says AI Will Cut the Workweek to 3.5 Days and Tells Gen Z EQ Matters More Than Ever
Dimon's annual shareholder letter dropped this week and the AI sections are generating serious conversation. He is bullish on long-term quality of life gains and unusually direct about short-term disruption risk, saying AI will "definitely eliminate some jobs" and that deployment speed could outpace adaptation if businesses and governments do not coordinate. He also doubled down on emotional intelligence as the skill that matters most going forward.
My hot take - The EQ point is the one I keep coming back to. Every skills readiness index right now is showing the same result: the skills AI is making more valuable are human skills, specifically critical thinking, communication, and the ability to work well with people you disagree with. The organizations still treating those as soft add-ons are going to find out the hard way that they are actually load-bearing walls.
04 Research · April 6, 2026 · Newmark
AI and the Future of Office: Quantifying Workforce Change Through 2030
Real estate research firm Newmark released a detailed study on how AI will shape office-using employment through 2030. Their base case projects essentially flat office employment growth, which would be historically unprecedented outside of a recession. Their point: AI is acting as a structural headwind to labor-driven office demand, and the companies and industries most exposed are not the ones most people would guess.
My hot take - The finding that matters most to me: 52% of AI interactions are being classified as augmentation versus 45% automation, based on Anthropic's January Economic Index. If that pattern holds, more jobs get restructured than replaced. But "restructured" still means significant disruption for the people living through it, and most workforce plans are not accounting for that middle ground.
05 Podcast · April 8, 2026 · Trust Insights
In-Ear Insights: AI and the Future of Work in 2026
Trust Insights published a sharp conversation this week on the METR report projecting that only domain experts, "the senior," will survive the next major wave of AI capability advancement. They also discuss a real company that scaled to $1 billion in revenue with a two-person team using agentic AI. Not as a thought experiment. As an actual current business operating right now.
My hot take - The $1 billion, two-person company story is not a prediction about where everything is going. It is a preview of one possible path. I do not think most organizations are 18 months from looking like that. But the direction of travel is clear, and the question HR leaders and founders need to be sitting with is not "will this affect us." It is "when it does, what is our answer for the people who built the company with us?" Or as an old friend said to me - so 2 person Ai companies are just going to sell to other 2 person Ai companies and where does that get us?
"The future of work will not be defined by what technology makes possible. It will be defined by what we decide is acceptable."
— Kristy McCann Flynn
I want to close this issue with something direct about what I think is broken in the broader conversation around work, ethics, and change management. Not just the technology piece, but the whole operating framework most organizations are using to navigate this moment.
Change management has become performance art. The standard playbook, communicate, train, reinforce, was designed for a world where change happened in defined episodes with a beginning and an end. That world is gone. AI is not a project with a go-live date. It is a continuous condition. Organizations need to build change capability permanently into how they operate, not deploy a program, declare victory, and move on to the next initiative.
AI ethics at work is being treated as a legal exposure problem rather than a moral commitment. Most corporate AI ethics frameworks I've reviewed were written by legal teams, not ethicists, and they are designed to limit liability rather than to genuinely grapple with what it means to treat people fairly as AI reshapes the work they've built their careers around. Workers feel the difference even when they cannot name it.
The consent problem is being actively avoided. When an organization deploys AI to analyze how employees communicate, track their productivity patterns, or assess engagement levels, the people being analyzed are rarely the people who made the deployment decision. That asymmetry of power is not just a policy question. It is an ethical one, and the organizations treating it as the former are accumulating trust debt that will eventually come due.
We keep measuring the things that are easy to count instead of the things that actually matter. Most organizations measure people investment through productivity output and retention rates. These are lagging indicators that tell you what already happened. The leading indicators, trust levels, psychological safety, manager quality, and whether people have any real directional clarity about their work, are harder to capture and so they mostly do not get captured at all. We optimize for what we can measure and act as though that represents the full picture.
The "best place to work" industry has become a marketing channel. I have been inside this process more than once. Winning one of those designations is not the same as being a good place to work. The methodology is mostly self-reported, the incentive to manage the submission process is substantial, and I have watched companies with genuinely dysfunctional cultures walk away with awards because they knew how to fill out the application. Recognition should carry weight. Right now, it mostly carries brand value, which is a different thing entirely.
What does an ethical approach to the future of work actually look like in practice? It starts with one commitment that sounds straightforward and turns out to be genuinely hard: tell your people what you are doing, why you are doing it, and what it means for them, before you do it. A real conversation, not a communication cascade. Change Management 101.
That takes more courage than any technology deployment. It is also the difference between organizations that build lasting loyalty and organizations that hit their efficiency targets and spend the next three years wondering why engagement keeps declining and their best people keep leaving.
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Until Next Time
This newsletter exists because the conversation about work deserves more honest voices. People who have actually built teams, led through hard moments, sat in the rooms where the real decisions get made, and are willing to say out loud what they see. I hope this qualifies as I am a 20-year HR Veteran and 3x Work Tech Founder and I know a few things, learned a few things and failed more times than I can count - but got up again to try again better every day. That is me in a nutshell.
Next issue I'm going deep on the HR Tech stack. What is actually worth buying right now, what has been dramatically over-hyped, and where I think the real white space is for the next generation of tools. If you have a product in this space and want to make the case for why it belongs on the list, reach out.
Reply to this email. I read every single one.
Kristy McCann Flynn
CEO & Founder, 127 Ventures
Advisor & Investor: Relate · Granted · RallyBright · and soon to be Previ
Executive Coach · Keynote Speaker · Forbes Coaching Council