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.
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