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

Ep. 577 - International Council for Small Business (ICSB) COO Skye Blanks - How To Turn Any Vision Into a Successful Reality

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

Second in Command with Cameron Herold

Business, Management, Careers, Entrepreneurship

4.9 • 224 Ratings

🗓️ 7 May 2026

⏱️ 44 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

What happens when you’re the glue holding a global mission together, but the glue starts to crack?

In this electric conversation, Sivana Brewer digs into the trenches with Skye Blanks, COO of the International Council for Small Business, an entrepreneur, and a relentless global operator. They expose the raw truth behind cross-border team dynamics, the weight of relentless travel, and the personal toll of constant responsibility. This episode tears open the unfiltered reality of getting things done, teaching accountability, and building operational systems when the stakes and time zones are always changing.

Listen now or risk missing the proven tactics and hard-won lessons that separate thriving leaders from burned-out managers. If you’re ready to weaponize transparency, claim your seat at the table, and cut through nonprofit noise, this conversation is for you.

Timestamped Highlights

00:31 – The “born operator” mindset that shaped a global COO

02:36 – The hidden power of loyalty and facing down risks bigger than Deloitte

05:35 – How do you keep policymakers, professors, and entrepreneurs moving together?

10:34 – The stop-doing list: Skye’s ruthless system for switching hats daily

15:06 – The radical transparency tactic that keeps remote teams accountable

18:16 – What’s really at stake when culture fails, and no one steps up

23:58 – Skye’s blueprint for replicable, world-class events—anywhere

29:23 – Why firing people and failed partnerships still sting at the top

34:18 – The “humane entrepreneurship” concept that rewrites how leaders show up

About the Guest

Skye Blanks is the Chief Operating Officer of the International Council for Small Business (ICSB), where he works closely with executive leadership to scale operations and support small and medium-sized enterprises globally. He is also the founder of Premo Cannabis and serves in advisory and board-level roles, bringing a hands-on operator’s perspective shaped by building and leading organizations. His work centers on execution, governance, and being an effective second-in-command.🔗 LinkedIn | Website

Mentioned Resources


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 teams to grow sustainably.

đź”— Connect with Sivana on LinkedIn

Important Links


The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

Sponsored by:

Redirect Health - Affordable healthcare benefits designed to make traditional insurance optional, with 24/7 access to primary care and Rx support that helps businesses reduce costs while keeping employees covered.

Learn more: http://www.redirectcoo.com/

Transcript

Click on a timestamp to play from that location

0:00.0

to ask those hard questions and say, hey, I had this difficult situation. How do I navigate that?

0:04.5

And so I like to say, as a CEO, you can't be, I guess, tied down to just one thing.

0:09.5

You do the work outside work to be a better leader. And so a lot of that comes from, hey,

0:15.5

let me read this article. Let me talk to these people about this issue. Let me learn more

0:19.9

about the people I'm interacting with.

0:24.0

Welcome to the Second in Command podcast, produced by the C.O. Alliance and brought to you by its founder, Cameron Harold.

0:32.0

In the Second in Command podcast, we talked to top CFOs who share the insights, strategies, and tactics that made them the

0:39.1

chief behind the chief.

0:40.9

And now here's your co-host, former CEO of a multi-eight-figure remote company and alumni

0:46.6

member of the COO Alliance, Savannah Brewer. Today's guest is Sky Blanks, the chief operating officer of the International Council for Small Business,

1:02.0

where he helped scale global operations that support small and medium-sized enterprises across countries, cultures, and systems.

1:10.0

Sky is also the founder of Primo Cannabis and serves in advisory and board level roles,

1:15.6

bringing a rare blend of institutional leadership and true operator experience.

1:20.6

In this conversation, we dig into what it really means to be an effective second in command.

1:25.6

We talk about how to coach teams to hold each other accountable instead of relying on

1:31.2

top-down enforcement, why writing things down is one of the most underrated leadership tools

1:37.0

and how to build systems that allow your organization to thrive without you constantly being

1:42.0

in the office.

1:43.8

We also explore the unique advantages and the challenges of being a young leader operating

1:49.0

at a high level and how to earn trust, credibility, and influence early in your career.

1:54.3

If you're a CEO operator or emerging leader focused on execution, governance, and building

2:00.0

teams at scale, this is a conversation you'll want to

...

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