By David Schumer, Managing Partner
Why human judgment remains the decisive edge in financial services, fintech, and private equity
Over the last few months, the AI conversation has swung toward predictable extremes. Some say it will replace most knowledge workers; others warn we’re “on the edge” of something irreversible. Anyone who has spent decades in recruiting knows that technology hype cycles come and go; and yet, one truth never changes: companies win or lose based on the quality of their people. That was true during the dot‑com boom when we founded Calibre One, and it remains true today.
As Matt Shumer wrote in his widely cited essay on AI, “Something Big Is Happening.” AI is reshaping workflows, compressing timelines, and expanding what’s possible across every function. His essay struck a chord because it was personal, grounded in lived experience, and directionally right: use AI aggressively, lean into trust, build relationships, and focus on judgment. We agree. Where we differ is not the direction of travel, but the timeline, the magnitude, and the hiring implications. Without recruiting and developing the right leaders now, companies risk hollowing out the very judgment, institutional memory, and cultural coherence that differentiate them. Without the right leaders today, you have no company tomorrow.
Companies, cultures, and competitive moats aren’t artifacts of code, they’re built by people. People who absorb a company’s operating rhythm. People who hold institutional judgment. People who communicate, align, escalate, and decide. People who can steer AI, not be steered by it. Judgment, accountability, and trust cannot be automated away. AI elevates high performers and exposes underperformers faster, but it doesn’t replace the people.
Across financial services, AI excels at triage, pattern detection, normalization, and summarization; however, humans remain indispensable for causality, ethics, escalation, and accountable decision‑making. The most credible analyses point toward augmentation, not elimination. AI enhances analyst leverage, it doesn’t remove the need for the analyst.
The pandemic taught us something similar: we are deeply social creatures, and we do our best work in high‑functioning teams. Team performance during COVID hinged on communication quality, trust, conflict management, and role clarity – none of which AI can replicate. If anything, AI raises the stakes. Analysts now will need to add value beyond just building models and writing investment memos with judgement and conviction.
Human–machine collaboration has always been an engine of progress. From the industrial revolution to the internet, human–machine teams consistently outperform standalone humans or standalone machines because superior process, judgment, and collaboration matter more than raw compute.
When IBM’s Deep Blue beat Garry Kasparov in 1997, conventional wisdom said human chess was finished. Newsweek’s May 1997 cover declared it ‘The Brain’s Last Stand.’ Instead, human–machine teams dominated both solo grandmasters and solo engines for almost twenty more years. That advantage eventually disappeared – computers got powerful enough to play perfect chess without us. But our world isn’t anything like a 64-square board with fixed rules. Ours is an open system of incomplete information, regulatory friction, relationships, trust, context and judgment calls. If human-AI collaboration defined peak performance in a closed system for nearly two decades, human-AI partnership will define excellence in our open industry for far longer, which means the quality of the people you pair with these tools is exponentially more important.
This is why companies get themselves into trouble when they respond to technological change with panic or denial.
Panic: “Freeze hiring because AI will do it.” Short‑term savings create long‑term damage. Replace too many junior roles and you collapse your leadership pipeline.
Denial: “Keep hiring the same profiles.” This ignores how dramatically AI is raising expectations of speed, throughput, and decision‑quality. The market is already pricing a premium for leaders, especially CEOs, CFOs, CROs, CTOs, and CPOs who can interrogate, govern, and communicate AI‑driven decisions.
Shumer writes, “the future is already here.” And he’s right – directionally.
Our view: the future is being built by people. The right ones will make all the difference.
At Calibre One, we’ve spent decades helping companies navigate disruptive transitions, from the internet, to cloud, to mobile, and now AI. Technology doesn’t automatically build organizations. Leaders do. The companies that win this era won’t be the ones with the most sophisticated models, but the ones who hire leaders who can use AI well, decide well, build trust, and scale teams through disruption.
AI is not an existential threat to talent.
It is a multiplier for the right talent.
And our work in finding those leaders has never been more essential.