Keeping Time on the Bridge: The Rhythm of Risk with Bradley Jewett

In this episode of Risk Is Our Business, Captain Michael Rasmussen opens a subspace channel with Bradley Jewett, Chief Financial Officer at LeadVenture and a seasoned operating executive who helped shape enterprise risk management inside Microsoft and BMC Software.

The discussion begins by contrasting bad risk management (periodic, siloed, and designed to check a box) with good risk management that actively informs how organizations make decisions. From there, Brad introduces the philosophy he championed at Microsoft: the Rhythm of Risk.

Rather than positioning risk as a separate function, Brad describes an approach where risk management keeps pace with the enterprise itself. Strategic planning cycles, annual operating plans, mergers and acquisitions, audit planning, SEC reporting, investor communications, and product roadmaps all become natural moments for risk to surface and influence outcomes. Risk moves in time with the business, strategic and operational, top-down and bottom-up.

Recorded over a live video link, the conversation also explores how this mindset was received by leadership, what it took to set expectations that risk should shape daily decisions, and why aligning risk to the organization’s cadence is far more effective than standalone frameworks or annual exercises.

The episode offers a practical, experience-led perspective on what it means to keep risk on the bridge, not as a warning light, but as a steady navigational rhythm guiding the enterprise through uncertainty at warp speed.