Can AI Replace a Chief of Staff? Cat Jordan on Running an AI-Native VC Fund

Cat Jordan, Chief of Staff at Crystal Venture Partners, talks with David Nebinski about why AI can take over repetitive tasks but can't replace a Chief of Staff's judgment, relationships, or negotiation skills. She shares how she helped build an AI-native venture fund, the tools Chiefs of Staff are using right now, and what she wishes she'd known before taking the role.

Connect with Cat on LinkedIn!

Full video

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Episode highlights:

02:00: Cat shares her career path through family business, startups, and IR becoming Chief of Staff at Crystal Venture Partners

04:00: She reflects on the CoS role as challenging and rewarding

07:15: She explains what “AI-native” means to the firm and how they are building one

13:15: Cat gives an example of resolving a miscommunication by calling the other person and working toward a resolution

21:30: Cat’s advice to new Chiefs of Staff: protect your time, peace, health, and personal routines

25:00: She talks about using agents for repeatable tasks

29:15: They discuss risk in using AI for consequential work, such as wire confirmations and deal negotiations

33:15: She discusses the reported growth in open CoS roles

35:45: Cat reflects on how the Chief of Staff role has evolved and become more widely understood

38:15: Cat encourages aspiring Chiefs of Staff to reach out to people whose careers they admire and to understand that the role varies by firm and executive

Connect with Cat on LinkedIn here!

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How AI is Changing The Chief of Staff Role in 2026 with Lauren Stein