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

Ep. 568 - TextNow COO Lindsay Gibson - How to Rebuild Culture (and Yourself) in Crisis

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

Second in Command with Cameron Herold

Business, Entrepreneurship, Careers, Management

4.9 • 225 Ratings

🗓️ 7 April 2026

⏱️ 46 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Ever felt like your company is running in circles while you quietly burn out, stuck between drive and exhaustion?

This episode is a blunt, emotionally raw exploration with Lindsay Gibson, COO of TextNow, a leader who’s walked away from the grind, returned for redemption, and rebuilt both companies and herself from the inside out. Sivana Brewer dives deep with Lindsay into the shock of losing vision, the chaos of remote work, and the brutal clarity that comes only after you’ve crashed headlong into career “success.”

If you’re tired of vague leadership advice and want exclusive, no-BS strategies for authentic leadership, unclenching burnout’s grip, and making culture work for real teams, listen right now. Miss this, and you might repeat the pain Lindsay barely escaped. These lessons are battle-forged, urgent, and unlike anything the standard playbooks offer.

Timestamped Highlights

[00:01:11] – The brilliant but gritty origin of TextNow: solving real pain for people who have to choose between a phone bill and groceries

[00:02:45] – Why Lindsay left her COO seat (twice) and what chasing “interesting work” really costs

[00:04:34] – The BlackBerry “return rate” disaster: how fixing buyer’s remorse became a master class in real-world delegation

[00:07:49] – The shocking truth: Engineering wasn’t the problem—here’s what really derails a company’s goals

[00:10:11] – The brutal downside of remote-first culture… and the hardest part of rebuilding accountability across a fractured team

[00:14:32] – Motherhood, loss, and the hidden price of ambition: Lindsay’s real talk on the boundaries she’ll never break again

[00:19:04] – “Dead bodies in the process”—when leadership feedback stings and the rebirth of authentic management

[00:27:54] – Why remote teams lose their soul (and how one-on-one connection fights back against isolation)

About the Guest

Lindsay Gibson is the Chief Operating Officer of TextNow, a disruptive, ad-supported mobile carrier serving millions who demand true flexibility in mobile communications. With over two decades shaping iconic tech cultures, including a 16-year run at BlackBerry, she’s mastered the hard edge of scaling, comeback leadership, and authentic team connection. Known for leading through crisis and comeback, Lindsay is a straight-talker driven by integrity and obsession with growth.

🔗 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.

🔗 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.

Transcript

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0:00.0

because it was global. So it was really, really hard because all of the same things apply, right?

0:06.3

Like people, they have to want to follow you. They have to believe in the vision for the team.

0:11.7

And we went through a period of a lot of like cost cutting targets. And so I did a lot of town halls,

0:20.6

a lot of travel, right? A lot of FaceTime. And then I made it my

0:25.3

goal to have a one to one with every single person at least once a year, which was a lot.

0:31.8

But and I do that here too. So we have something here called Donut Chats and I'm like they're actually one of

0:39.0

my favorite meetings of the day because it's not about work. The whole intention is just as an

0:43.3

opportunity to get to know people. Welcome to the second in command podcast produced by the

0:53.6

COO Alliance and brought to you by its founder, Cameron Harold.

0:58.1

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

1:06.4

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

1:18.4

Today on the Second and Command podcast, I am sitting down with Lindsay Gibson, the powerhouse CEO of Text Now, a mission-driven company redefining what it means to provide high-quality

1:29.7

free phone service at scale. Lindsay has spent nearly two decades leading through explosive

1:35.1

growth, reinvention, and operational transformation, including 16 years at BlackBerry and

1:40.9

two chapters as CEO at TextNow. We get into how she reset clarity inside the organization,

1:47.5

sharpening priorities, rebuilding accountability,

1:50.2

and re-grounding the culture so the team knows exactly where they're going

1:53.6

and what great execution looks like.

1:55.8

She also opens up about her own time management systems,

1:59.1

how her relationship to hard work has evolved,

2:01.9

and the leadership philosophy she's developed from scaling teams, supporting people through rapid

2:06.0

change and navigating the pressure that comes with growth. It's a grounded, honest, and deeply

...

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