Revenue Builders

Navigating the CRO Role while Building a Great Culture with Matt Nolan

Apr 24, 2025

Matt Nolan, Chief Revenue Officer at Redwood Software, dives into his extensive journey in global revenue strategies and scaling automation solutions. He discusses the crucial role of company culture in recruitment and the art of hiring proactively, emphasizing that strong leadership significantly influences team success. Matt shares insights on navigating board relations, the impacts of remote teamwork during the pandemic, and the importance of creating a high-performance culture that drives growth. Listeners gain practical strategies for building winning sales organizations.

01:05:51

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Episode guests

Matt Nolan

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Episode notes

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Quick takeaways

CROs must prioritize culture over individual achievement by fostering a team-based environment that emphasizes collaboration and accountability.

Effective recruiting is essential for a CRO's success, with strong connections yielding the best talent and enhancing overall performance.

Navigating board dynamics requires transparency and mentorship, enabling first-time CROs to build trust for strategic collaboration.

Deep dives

The Role of a First-Time CRO

Stepping into the role of a first-time Chief Revenue Officer (CRO) brings a unique set of challenges and learning experiences. It involves balancing the operational needs of the organization with the soft skills necessary for effective leadership. A key realization is that every word and action is closely observed by team members, making it crucial for the CRO to set the right tone and foster a positive culture. Building that culture becomes even more complex when faced with remote work scenarios, highlighting the need for innovative strategies to maintain team cohesion and accountability.

Intro

2min

Insights from a First-Time Chief Revenue Officer

5min

Evolving Responsibilities in Senior Sales Leadership

4min

Navigating Leadership in a New Culture

9min

The Imperative of Proactive Recruitment

25min

Integrating Revenue Impact Across Organizational Functions

2min

Strategic Talent Sourcing

10min

Leadership and Recruitment Dynamics

9min

In this episode of the Revenue Builders Podcast, hosts John McMahon and John Kaplan are joined by Matt Nolan, Chief Revenue Officer at Redwood Software. Matt shares his extensive experience in developing global revenue strategies, scaling enterprise automation solutions, and transitioning from venture capital to private equity environments. The conversation covers key lessons such as the importance of culture, the significant role recruiting plays in a CRO's success, the complexities of managing a board, and strategies for building top-performing sales teams. Matt emphasizes the critical nature of hiring ahead, discipline in recruiting, the layered impact of having strong leaders, and creating a high-performance, team-based culture that can drive prolific growth. Listeners will gain valuable insights on how to build and sustain a winning sales organization.

ADDITIONAL RESOURCES

Learn more about Matt Nolan:
https://www.linkedin.com/in/matthewanolan
https://www.linkedin.com/company/redwood-software/

Download the CRO Strategy Checklist: https://hubs.li/Q03f8LmX0

Read Force Management’s Guide to Increasing Company Valuation: https://hubs.li/Q038n0jT0

Enjoying the podcast? Sign up to receive new episodes straight to your inbox: https://hubs.li/Q02R10xN0

HERE ARE SOME KEY SECTIONS TO CHECK OUT

[00:02:02] Lessons from a First-Time CRO
[00:03:47] Building and Maintaining Company Culture
[00:04:45] Navigating Leadership During COVID-19
[00:06:05] Managing the Board and Leadership Challenges
[00:07:03] Scaling Revenue and Systems Thinking
[00:10:15] Recruitment and Team Building Strategies
[00:11:16] The Importance of Authentic Leadership?
[00:15:21] Fostering a Team-Based Culture
[00:20:39] Recruitment Pipeline and Talent Acquisition
[00:21:30] The Relentless Pursuit of Top Talent
[00:34:00] The Power of Networking and Recruiting
[00:35:14] Building a Leadership Team
[00:36:15] The Importance of Recruiting Top Talent
[00:39:10] Sourcing and Recruiting Strategies
[01:01:21] The Role of Culture in Building a Dynast

HIGHLIGHT QUOTES

"Recruiting is the foundation and culture is what sustains you and allows you to win multiple championships."
"Once you see the impact of having great people, you can't unsee it."
"You can be bad at everything, but if you're great at recruiting, you can cover for a lot of sins."
"Every word you say as a leader is internalized deeply by your team."
"You've got to be relentless about recruiting, it can't just be something you do when there's an opening."

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Revenue Builders

Navigating the CRO Role while Building a Great Culture with Matt Nolan

Episode guests

Podcast summary created with Snipd AI

Quick takeaways

Deep dives

The Role of a First-Time CRO

Cultivating a Team-Based Culture

The Importance of Mentorship and Managing Boards

Recruitment as a Core Responsibility

Aligning Culture with Performance

Remember Everything You Learn from Podcasts