Ep. 520 - Cory Raggi – How to Stay Grounded and Lead with Trust

Second in Command: The Chief Behind the Chief with Cameron Herold

In this episode of the Second in Command Podcast, guest co-host Sivana Brewer (Fractional COO for Remote Teams and former COO at Closers.io) sits down with Cory Raggi, COO of 1RDG The Financial Center, to talk about leading with empathy, navigating change, and building trust in teams both large and small.

Cory shares her journey from leading HR at a 15,000-person company to stepping into her first COO role at a fast-growing 80-person firm. She opens up about how she learned to adapt, communicate, and stay grounded in high-pressure situations and the three core practices that help her regulate stress and lead with clarity.

From learning to “roll on the edge” between people and performance to replacing stress with self-awareness, this conversation is packed with real-world leadership lessons for operators who want to grow without burning out.

Timestamped Highlights

[00:02:00] – How Cory went from HR leader to unexpected COO.

[00:03:00] – Redefining what a COO really does (and doesn’t do).

[00:06:26] – “Right people, right seats”: her mantra for solving every problem.

[00:08:12] – Building trust with the CEO and learning to push back.

[00:10:21] – Deprogramming corporate habits in a smaller company.

[00:13:07] – Leading teams without being the technical expert.

[00:17:13] – Building fast trust through humility and honest communication.

[00:19:25] – The mirror test: checking your own leadership energy first.

[00:22:00] – Balancing people and business why great leaders “roll on the rim.”

[00:23:40] – Running effective meetings that actually serve their purpose.

[00:28:16] – Leadership breakdowns most middle managers make.

[00:33:13] – How Cory learned to stay calm and centered under pressure.

[00:36:49] – The one-next-right-thing method for managing stress.

[00:42:00] – The isolation of being a COO—and how to find your support system.

[00:47:16] – What’s next for Cory personally and professionally?

About the Guest

Cory Raggi, SHRM-SCP is the Chief Operating Officer of 1RDG The Financial Center, a company providing integrated accounting, payroll, benefits, and wealth management solutions for business owners. With a background in HR and organizational leadership, Cory blends people-first management with operational structure, helping teams stay aligned, communicative, and focused through growth.

🔗 LinkedIn | Website | Podcast | Linktree

Resources & Mentions

• The Speed of Trust by Stephen M.R. Covey
• Crucial Conversations by Patterson, Grenny, McMillan & Switzler
• Meetings Suck by Cameron Herold
• Emotional Intelligence by Daniel Goleman

About the Co-Host

Sivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower fast-growing teams to thrive without burning out.

🔗 LinkedIn

Important Links

• Connect with Cameron: Website | LinkedIn
• Explore the COO Alliance - The World’s Leading Community for Seconds in Command
• Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
• Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
• Chat or video call with AI Cameron via Delphi