AI is accelerating faster than most organizations can process.

What feels like progress on the surface also introduces a deeper leadership question: As tasks get automated and outputs get polished instantly, how do we protect judgment, development, and human connection?

In this episode, we’re joined by Dan Riley, Co-Founder of RADICL, to explore the responsibility that comes with building and deploying AI inside the workplace. If humans created these systems, humans still shape their direction.

We talk about AI as a copilot, the risk of over-reliance, the value of creative friction, and why the future of work depends less on the tools themselves and more on the intentionality behind how we use them.

Technology will keep advancing. The real differentiator will be leadership.

"The market just isn't ready for us." After 20 years advising HR tech founders, executives, and investors, Sarah White has heard that line more times than she can count — and she has zero patience for it.

In this episode of Work Tech Weekly, Sarah joins Steve Smith to break down what's really stalling growth, killing deals, and quietly holding HR tech teams back. They dig into why unclear positioning costs you customers and acquisitions, how a $100M company was leaving growth on the table because of internal misalignment, and where AI is reshaping the work tech stack faster than most people realize.

If you're a founder, executive, or investor wondering why you’re stuck in neutral, this conversation will give you a sharper lens on what's actually going wrong — and how to fix it.

In this episode:

• Why "the market isn't ready" is almost always a go-to-market problem

• How messaging mistakes kill acquisitions before a deal ever closes

• The internal alignment gap that's holding more companies back than they realize

• Where AI is quietly reshaping payroll, workforce management, and learning

AI didn’t just speed up work. It changed what matters at work. For decades, talent assessments measured traits, cognitive ability, and technical skills. That made sense when roles were stable and hard skills lasted longer than your iPhone upgrade cycle.

But now? AI handles more of the execution. Technical skills commoditize fast. And the real differentiator isn’t what you know — it’s how you think. In this episode of Work Tech Weekly, I sit down with Dustin Clinard, CEO of Ignis AI, to talk about what happens when the baseline shifts but our measurement tools don’t.

We dig into why traditional assessments may be misaligned with the AI era and whether human skills have quietly become the hardest skills of all. AI can now build a presentation deck in seconds — probably better than you can. But can it decide what story the deck should tell? “The part that [AI] can't do is think, ‘What do I want it to say and in what order?’ That's my judgment call to make,” Dustin says. “Once I decide that, the building-it part can happen really quickly.”

If AI is accelerating execution, judgment becomes the edge. The question is: can we measure it? If you’re rethinking hiring, development, or what performance actually looks like in an AI-first world, this one’s for you.

From an investment perspective, the Work Tech market in 2026 looks… oddly healthy. The charts are trending up, capital is flowing again, and 2025 clocked in at $6.24 billion in funding — the third-biggest year the sector has ever had. On paper, it’s momentum, if you’re brave enough to say it out loud. However, most founders’ lived reality feels so far from OK.

In this episode, we are talking with George LaRocque, the Founder and Chief Analyst at WorkTech (the research and advisory firm, not this podcast … yes, I know it’s confusing.) We break down his 2025 Work Tech investment recap because he has some of the best research and clearest views in the industry on what’s happening beneath the surface of Work Tech: where investors are placing bets, where buyers are actually spending, and which companies may not survive this cycle.

We dig into today’s somewhat paradoxical and often contradictory Work Tech investment dynamics. The disconnect is psychological and structural: Investors see stability, founders feel selectivity. Raising isn’t about having a cool AI story anymore — it’s about adoption, ROI, survival.

Why do hiring processes collapse under volume? Why has “perfect fit” made trust disappear from recruiting? Can AI be both a problem and a solution? Where the hell is Left Miami?

In this episode of the Work Tech Weekly podcast, Steve Smith talks with Claire McTaggart — founder and CEO of SquarePeg — about how modern hiring systems trained candidates to game the process, and why recruiters are now drowning in low-signal applicants.

Drawing on real-world fraud investigations and hands-on work with talent teams, Claire explains how keyword-driven screening flattened resumes into sameness, why asking HR to police fraud is unsustainable and how incentives created today’s mess.

They also discuss where AI has amplified the problem, where it can actually help, and what changes would be required for screening tools to reward authenticity, context and real capability again.

Why do global payroll implementations that were supposed to take 12 months still drag into year two?

In this episode of the Work Tech Weekly podcast, Steve Smith sits down with Jerome Gouvernel — CEO and co-founder of datascalehr — to unpack why global payroll projects keep breaking down, and why the industry keeps selling a model that can’t scale.

Jerome draws on 20 years of experience building global payroll systems to explain why traditional implementations are still waterfall, why promises of “full compliance” are economically fragile, and why most integration work forces teams to learn system languages they’ll never use again.

They also dig into the growing hype around enterprise AI — why compliance can’t be “vibe coded,” why auditability matters more than automation, and why you need a data strategy before you can have a real AI strategy.

What makes sales kickoffs either catalytic or a Vegas-grade waste of money?

You’ll find out in this episode of the Work Tech Weekly podcast, when Steve Smith welcomes Ryan Estis — former Fortune 500 CRO, bestselling author, and leadership keynote speaker — for a candid conversation on sales, leadership, kickoffs and (of course) AI.

They dig into why human-centered leadership is a performance multiplier. Right now, command-and-control sales leaders are falling behind, and empathy is becoming the most valuable (and hardest) skill in sales. They wrap up by talking about why the time for AI experimentation is over and how the most effective teams are using it to free up time for empathy, coaching and focus on the customer.

A new podcast is launching for people who want the inside scoop on what’s going in the Work Tech industry and its sometimes chaotic and ever-evolving landscape.

The Work Tech Weekly Podcast is hosted by Steve Smith, Managing Director of Growth at Rep Cap. When he talks with the founders, executives, and other industry muckity-mucks that make things happen in the industry, he aims to surface the interesting tidbits that usually happen off-mic. You know, the signals hiding in plain sight. And yes, the weird details that say more than a polished press release ever could.

In this trailer, you’ll get a behind-the-scenes look at the show before we launch: candid, opinionated, sometimes messy, and focused on giving you real context in less time. If you care about where work technology is headed and want to understand what’s actually happening beneath the surface, this podcast is for you.