Matt Nolan, the CRO of Redwood Software, shares valuable insights from his journey scaling a revenue organization past $200M. He discusses the crucial shift from being a deal-maker to a system-builder and how to navigate the complexities of cultural integration post-acquisition. Matt highlights the importance of authentic leadership in building trust and emphasizes that understanding existing cultures is key when implementing new strategies. He also touches on the challenge of balancing learning with initiating change as a new leader.
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insights INSIGHT
CRO Shift to Systems Thinking
Scaling revenue means shifting from individual deals to systems thinking for sustainable growth.
The CRO must focus on turning all "what's not working" into "what's working" within the organization.
question_answer ANECDOTE
Rebuilding Legal from Scratch
Matt rebuilt the entire legal function by personally recruiting a general counsel and reshaping the team.
This was a critical task nobody else could move but vital for organizational health and trust.
insights INSIGHT
Earning Board Trust and Balancing Views
Successfully interfacing with a board requires earning trust, especially when your vision differs from theirs.
Balancing their PLG expertise with introducing outbound and strategic account programs was key to scaling.
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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.”
Revenue Builders