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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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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