

Surrounding Yourself with a Great Team with Matt Nolan
7 snips May 4, 2025
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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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.
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.
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.