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044 OpsJobs | The AI skill gap that's starting to show up in CoS hiring

Author

Scott Amenta
May 14, 2026

Hi there,

86% of Chiefs of Staff use AI every day. Only 7.3% have actually built it into how they work.

That gap is showing up in hiring. Organizations aren't just looking for operators who can use AI tools. They're looking for operators who can lead on AI — who can run the internal audit, build the case for tool adoption, and brief the CEO with a point of view. That's a different skill set, and most candidates don't have it yet.

We published new data this week from the COSN AI Readiness Diagnostic that breaks down exactly where the community stands and what separates the operators who are pulling ahead.

If you're actively looking or just keeping your options open, this is worth reading. The operators who build AI-native workflows now will have a structural advantage in the next job search that's genuinely getting harder to close.

And if you want to do the work, not just read about it, the COSN AI Fellowship is where Chiefs of Staff are building these skills together. Applications are open.

Be the strategic partner to Sage’s CEO at a mission-driven healthtech company transforming senior care. This is a high-impact, high-visibility role where you’ll own critical initiatives and help scale Sage through its next phase of growth.

💰$190k-220 | 📍New York

Work directly with the Managing Partner at a tech-forward law firm serving startups and founders. This is an operational partner role at the intersection of law, technology, and entrepreneurship, with room to grow into senior leadership.

💰$100k-125k | 📍Remote

Chief of Staff Roles

Chief of Staff (Generalist) – Build.inc
💰$175k-230k | 📍New York, NY

Chief of Staff – Colla Health
💰Not listed | 📍United States

Chief of Staff – Veriswap
💰Not listed | 📍New York, NY

Deputy Chief of Staff – Anaplan
💰Not listed | 📍Manchester, UK

Chief of Staff – atares
💰Not listed | 📍Munich, Germany

BizOps Roles

Strategy & Operations – Gigs
💰$140k-190k | 📍New York, NY

Director, Operations – NBCUniversal
💰$150k-175k | 📍Universal City, CA

US-Senior Manager – Apple
💰Not listed | 📍Miami, FL

Is your Exec team ahead of the AI curve, or behind it?

Honest answer: you probably don't know. Neither does anyone else, because no one's measuring it.

We're changing that. Fill in our anonymous survey and we'll send you the full cross-industry report so you can finally see where you stand.

Anonymous, 2-3 min

Director, Legal & Compliance – NewtonX
💰$170k-180k | 📍United States

All Ops Roles

Field Marketing – Freed
💰$145k-175k | 📍New York, NY

Product Manager - Growth – Luma
💰Not listed | 📍San Francisco, CA

Revenue Operations Program Manager – CallRail
💰Not listed | 📍Atalanta, GA

Upcoming IRL events:

Upcoming Virtual events:

Get in on the fast track, join our Talent Network

Whether you're actively searching or just open to the right thing, we're building a curated database of Chief of Staff talent to match against roles as they come across our desks. Submit your profile here and we'll reach out when something fits.

Thanks for reading!

Scott
Founder, Operators | LinkedIn