Surrounding Yourself with a Great Team with Matt Nolan
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 team [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 Enjoying the podcast? Sign up to receive new episodes straight to your inbox: https://hubs.li/Q02R10xN0 Check out John McMahon’s book here: Amazon Link: https://a.co/d/1K7DDC4 Check 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/Q02Zb8WG0 Read Force Management's eBook: https://www.forcemanagement.com/roi-of-sales-messaging