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

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

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

Second in Command with Cameron Herold

Management, Careers, Entrepreneurship, Business

4.9 • 224 Ratings

🗓️ 21 October 2025

⏱️ 52 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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


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


Transcript

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0:00.0

I spent 17 years at a company with, you know, 15,000 employees.

0:04.1

Now I'm at an organization that has 80 people in the building.

0:07.4

And I was very scared that I would have to do everything.

0:12.9

And I fortunately am somewhere where if I make a business case,

0:16.3

we can invest in a hire or a technology.

0:19.3

And that was something that was important to me.

0:25.7

Welcome to the Second in Command podcast, produced by the COO Alliance and brought to you by

0:31.6

its founder, Cameron Harold. In the Second in Command podcast, we talked to top COs who share the insights, strategies, and tactics that made them the chief behind the chief.

0:42.6

And now here's your co-host, former COO of a multi-eight-figure remote company and alumni member of the COO Alliance, Savannah Brewer.

0:54.8

Today on the Second and Command podcast, we are joined by Corey Ragge, CEO of OneRDG, the One Financial Center.

1:03.3

Corey oversees strategy, culture, and seamless operations while actively serving her community

1:08.2

as vice president of the RDG Foundation.

1:12.1

She also has spent many years in HR, including working at a 15,000 person company,

1:17.9

which is part of the conversation today about how she has transitioned from,

1:23.1

going from larger corporate companies to a smaller 80-person startup.

1:28.1

We also hear how she's learned not to get stressed, really keeping herself grounded and regulated

1:36.0

in high-pressure environments and revealing the three core practices in ways of thinking to do that.

1:42.1

We dive into her leadership principles shaped by years in HR, exploring

1:46.9

how to build trust quickly in a new role, which she's learned about running effective meetings

1:52.1

and keeping communication tight across the team and how leadership shifts when managing an 80-person

1:58.1

team versus a 15,000-person organization.

2:05.7

So if you're looking to strengthen your operational leadership while staying grounded and people-focused,

...

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