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 leaderQUOTES[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-nolanEnjoying the podcast? Sign up to receive new episodes straight to your inbox:https://hubs.li/Q02R10xN0Check out John McMahon’s book here:Amazon Link: https://a.co/d/1K7DDCCheck out Force Management’s Ascender platform here: https://my.ascender.co/Ascender/Force Management is hiring for a Sales Director. Apply here: https://hubs.li/Q02Zb8WG0Read Force Management's eBook: https://www.forcemanagement.com/roi-of-sales-messaging Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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