Leading, Complex Systems, and AI with Jessica Block

Jessica Block thinks about the technological transformation we are all experiencing the way physicists think about quantum mechanics – as a system where observation changes the outcome and where the most interesting things happen at the edge of possibility.

In this episode of Law://WhatsNext, we catch up with Jess, Executive Vice President at Factor – a former theatre major turned legal tech executive who's spent her career electrifying complex systems. From her early days in eDiscovery at FTI Consulting to her multifaceted roles at Factor (including a stint as CFO), she embodies the kind of cross-functional thinking and leadership that thrives in periods of rapid transformation.

What makes this episode essential listening is Jessica's ability to articulate the delicate balance between structure and emergence when leading through technological upheaval. "We're constantly stitching together partial insights to get to coherence," she explains, describing how Factor is approaching the GenAI moment not as a traditional tech rollout but as a complex system that requires cultivation rather than control.

The conversation takes unexpected turns as Jessica reflects on Factor’s strategic pivot into AI-first legal solutions. The Sense Collective, formed during what she calls "that constant loop of discovery and disappointment" in early 2023, has positioned Factor at the center of a community exploring how generative AI will reshape legal work. 

We venture into philosophical territory when Jessica references complex systems theory and Neil Theise's "Notes on Complexity" drawing parallels between consciousness as a transducer and the kind of emergent organisational change Factor is nurturing. These moments of introspection reveal why building and leading in this space requires not just technical expertise but a willingness to confront existential questions about how we approach work itself.

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