Revenue Builders

Surrounding Yourself with a Great Team with Matt Nolan

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.

07:55

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Episode guests

Matt Nolan

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Quick takeaways

As a CRO, transitioning from a deal-focused role to systems-oriented leadership is essential for scaling revenue organizations successfully.

Building trust through authenticity and cultural integration is crucial for a new CRO to effectively implement strategic changes and foster growth.

Deep dives

Evolving as a Senior Leader

As a Chief Revenue Officer (CRO), the role shifts considerably from being heavily involved in sales deals to adopting a broader systems-oriented perspective. The CRO must focus on organizational structure, including determining team sizes for Business Development Representatives (BDRs) and Sales Development Representatives (SDRs), while managing various sales motions within the company. This complexity requires the CRO to hire strong leaders who can handle customer relationships and operational responsibilities, allowing the CRO to concentrate on strategic oversight. For example, improvements in the legal department, which initially faced challenges, became one of the CRO's key successes after integrating a general counsel and transforming that function.

Navigating the Challenges of Revenue Leadership

4min

Navigating Leadership Transitions and Cultural Change

4min

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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Revenue Builders

Surrounding Yourself with a Great Team with Matt Nolan

Episode guests

Podcast summary created with Snipd AI

Quick takeaways

Deep dives

Evolving as a Senior Leader

Building Trust and Navigating Culture

Remember Everything You Learn from Podcasts