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

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/1K7DDC

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

In this episode of the Revenue Builders Podcast, hosts John McMahon and John Kaplan are joined by Marcello Gallo, Chief Revenue Officer at Sigma Computing. The discussion dives into Marcello's extensive experience in enterprise sales leadership, including his non-traditional path, lessons from leading roles at various companies, and the importance of structure, mentorship, and continuous learning. Marcello shares valuable insights on transitioning from technical roles to sales, territory management, and the significance of aligning with customer needs to drive value. The conversation also emphasizes the importance of having a growth mindset, understanding customer environments, and leveraging product-market fit for sustained success.

ADDITIONAL RESOURCES

Learn more about Marcello Gallo:
https://www.linkedin.com/in/gallomarcello/

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

[00:01:53] Marcello's Journey into Enterprise Sales
[00:08:13] The Importance of Structure in Sales
[00:28:37] Navigating Major Accounts and Complex Sales
[00:34:32] Understanding the Champion's Role in Sales
[00:35:15] Building Strong Relationships with Champions
[00:37:59] The Importance of Predicting and Preparing for Objections
[00:39:14] Role-Playing and Preparation Techniques
[00:40:05] Leadership and Helping Teams Get Unstuck
[00:42:03] Lessons from Climbing the Corporate Ladder
[00:43:21] The Value of Enablement and Territory Management
[00:46:20] Adapting to Market Changes and Customer Feedback
[00:53:59] Choosing the Right Opportunities and Taking Risks
[01:04:50] Sigma Computing's Growth and Opportunities

HIGHLIGHT QUOTES

“If you can't bet on yourself, who can you bet on?"
“Knowledge is courage.”
“You get delegated to those that you sound like.”
“Hire the people commensurate to the territory that you have open.”
“Don't confuse position with opportunity.”

In this short segment of the Revenue Builders Podcast, we revisit the discussion with Jane Thompson of BigPanda to unpack the art and science of selling into strategic accounts. Jane shares hard-won wisdom on navigating multi-divisional enterprises, building champions across layers of influence, and translating technical capabilities into board-level business value. If you want to elevate from tactical selling to true strategic impact, this episode delivers the roadmap.

KEY TAKEAWAYS

[00:00:45] Focus beyond standard research—find personal executive insights to connect meaningfully.

[00:01:15] Strategic sellers must bridge technical solutions to business outcomes.

[00:02:00] Map value by stakeholder: technical director, VP, CIO—tailor it to each.

[00:03:30] Selling to multi-divisional organizations requires managing multiple champions, needs, and value props.

[00:04:15] Ecosystems are interdependent—solutions impact multiple departments.

[00:05:00] Use the “M and W Effect” to navigate accounts vertically and horizontally.

[00:06:00] Prevent single-threading—schedule multiple meetings at once and communicate openly.

QUOTES

[00:01:20] “Anyone can go read a 10-K, but go find personal tidbits that help you build a champion at every level.”

[00:01:55] “You have to translate what you do into business issues—or you’re not going to be a good strategic account rep.”

[00:02:40] “If you think in a strategic sense, mapping value by stakeholder becomes second nature.”

[00:04:00] “It’s a skill to unify multiple divisions with multiple stakeholders into a single ROI conversation.”

[00:05:10] “If you’re not moving up and down in the org chart, you won’t make it in strategic accounts.”

[00:06:05] “Be transparent—reach high and wide without being sneaky. It works if done right.”

Listen to the full conversation through the link below.
https://revenue-builders.simplecast.com/episodes/selling-into-strategic-accounts-with-jane-thompson

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:
Revenue Builders Podcast, John Kaplan, John McMahon, Force Managementhttps://hubs.li/Q02Zb8WG0

Read Force Management's eBook:
https://www.forcemanagement.com/roi-of-sales-messaging