Turn Risk Into Your Biggest Advantage with Courtney C. Davis
August 12, 2026
In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Courtney C. Davis, Executive Vice President and Global Education Practice Leader at Hub International. Drawing on nearly two decades of experience spanning large brokerages and managing enterprise risk across 12 schools and a medical center at the University of Chicago, Courtney offers a masterclass in modernizing organizational risk.
Podcast Host: Jason Reichl
Executive Producer: Don Halliwell
In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Courtney C. Davis, Executive Vice President and Global Education Practice Leader at Hub International. Drawing on nearly two decades of experience spanning large brokerages and managing enterprise risk across 12 schools and a medical center at the University of Chicago, Courtney offers a masterclass in modernizing organizational risk.
Courtney breaks down why risk management can no longer exist as a restrictive "control function" or administrative checklist. Instead, she outlines her philosophy on turning risk into an operational enablement tool—shifting from the "office of NO" to the "office of K-N-O-W". From navigating tight market capacity and leveraging strategic storytelling to gain carrier buy-in, to evaluating risk maturity through proactive organizational outreach, Courtney delivers practical strategies for risk professionals across education and the commercial sector alike.
Podcast Host: Jason Reichl
Executive Producer: Don Halliwell
Episode Highlights:
- 00:00:28 – A Dual Perspective: Courtney’s 19-year journey spanning large brokerages and enterprise risk management at the University of Chicago.
- 00:01:18 – Forces of Change: Navigating rapid social media pressures, changing pedagogy, and economic headwinds in education.
- 00:02:24 – The "Office of K-N-O-W": Why everyone is a risk manager and how risk leaders can help teams get to a safe "yes".
- 00:03:37 – Mindset Over Control: Shifting risk management from insurance procurement to a decision-support framework.
- 00:05:45 – Measuring Risk Maturity: Why inbound calls from operational teams are the true momentum indicator of risk management success.
- 00:07:49 – Optimizing Risk for Growth: Learning to view and pitch organizational risk as a value driver rather than a negative weight.
- 00:09:53 – Storytelling in Insurance Procurement: Moving past standard PDF applications to highlight proactive board engagement and risk mitigation.
- 00:13:32 – Small Business Risk Culture: Building continuous risk education and operational safety into everyday workflows.
- 00:14:45 – Boardroom Presence: Advocating for risk managers to engage directly with senior leaders and board members.
- 00:18:29 – Market Trends & Cyber Risks: Addressing hard market dynamics, AI optimization, and aging physical infrastructure.
- 00:20:48 – "Risk or Too Risky": Courtney’s rapid-fire takes on scenario testing, legacy vendors, and policy compliance.
- 00:22:15 – The 19-Year Takeaway: Why no organization ever regrets over-communication and engaging the right stakeholders.
Episode Resources
Risk Management: Brick by Brick is handcrafted by our friends over at: fame.so
Previous guests include: Seth Hausman of Kraus-Anderson Insurance, Matthew Meyer of The Horton Group, Diana Rich of Foundation Building Materials, Christy McHenry of Suffolk Construction, Mark Rieder of NFP, and Cory Mangum of Primoris Services Corporation.
Check out the three most downloaded episodes:
Previous guests include: Seth Hausman of Kraus-Anderson Insurance, Matthew Meyer of The Horton Group, Diana Rich of Foundation Building Materials, Christy McHenry of Suffolk Construction, Mark Rieder of NFP, and Cory Mangum of Primoris Services Corporation.
Check out the three most downloaded episodes:
- Managing Your Risk Portfolio with Seth Hausman
- Focusing on Specialization with Matthew Meyer
- Risk Management is Everywhere with Diana Rich
If you are interested in being a guest on Risk Management: Brick by Brick, please complete this form: fame.so/trs-guest