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Surrounding Yourself with a Great Team with Matt Nolan

Surrounding Yourself with a Great Team with Matt Nolan

Revenue Builders vor 1 Jahr

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7:55

In this short segment of the Revenue Builders Podcast, we revisit
the discussion with Matt Nolan, CRO of Redwood Software, to
discuss what it really takes to scale a revenue organization
beyond the $200M mark. Matt shares what he’s learned stepping
into the CRO role—shifting from deal-maker to system-builder,
navigating cultural integration post-acquisition, managing board
dynamics, and building trust through authentic leadership. If
you're a sales leader, aspiring CRO, or operating in a private
equity-backed company, this candid conversation is loaded with
actionable insights.

KEY TAKEAWAYS

[00:00:30] The shift from deal involvement to systems thinking as
a CRO

[00:01:40] Navigating complexity: PLG, SLG, and assisted motions
in one org

[00:02:15] Tackling organizational friction points no one else
can move

[00:03:00] Building credibility with a board that has a different
go-to-market background

[00:03:45] The challenge of balancing learning vs. initiating
change as a new leader

[00:05:00] Why being authentically yourself is the best
leadership strategy

[00:06:15] How to build trust without gutting legacy teams

[00:06:45] Culture wins: no account conflicts, cross-region
harmony, and shared mission

[00:07:15] Going from “best kept secret” to magic quadrant leader

QUOTES

[00:01:45] “My job is to go turn all the ‘what's not working’
into ‘what's working.’”

[00:02:10] “There are some rocks in the business that only the
CRO can move."

[00:03:05] “You’ve got to earn trust to make big moves—especially
when your vision differs from the board’s.”

[00:05:00] “The only way to do it is to be yourself—even if that
means being more open than most."

[00:06:50] “I’m proud of a very corny thing: no account conflict
has ever escalated to me in three years.

[00:07:00] “We were the best kept secret in software—now we’re in
the magic quadrant.”

Listen to the full conversation through the link
below:

https://revenue-builders.simplecast.com/episodes/navigating-the-cro-role-while-building-a-great-culture-with-matt-nolan

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Check out John McMahon’s book here:

Amazon Link: https://a.co/d/1K7DDC

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here:

https://my.ascender.co/Ascender/

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Hosted by five-time CRO John McMahon and Force Management
Co-Founder John Kaplan, the Revenue Builders podcast goes behind
the scenes with the sales leaders who have been there, done that,
and seen the results.

This show is brought to you by Force Management. We help
companies improve sales performance, executing their growth
strategy at the point of sale.

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