Revenue Builders Podcast
Episode: Navigating the CRO Role while Building a Great Culture
Host(s): John Kaplan, John McMahon
Guest: Matt Nolan, Chief Revenue Officer, Redwood Software
Date: April 24, 2025
Episode Overview
This episode dives deep into what it’s really like to step into the Chief Revenue Officer (CRO) seat for the first time, particularly in a private equity-backed company, and the challenges of building and scaling a winning sales culture. Matt Nolan shares his journey, lessons learned, and actionable best practices gleaned from transforming teams and growing Redwood Software’s revenue from $80M to over $200M. The conversation goes far beyond operational playbooks to address softer leadership skills, culture-building, board management, and—above all—the critical role of relentless recruiting.
Key Discussion Points & Insights
1. The Reality of the CRO Role
Timestamp: 02:17–08:55
- Operational discipline vs. deeper responsibilities:
- The “easy part” is establishing cadence and operational rigor. The “hard part” is realizing how deeply people absorb and internalize every word and action from the CRO.
- "Everything you say and do is being watched and internalized." – Matt Nolan (02:54)
- Culture is paramount: The CRO sets the tone for sales and often for the entire organization.
- Building culture virtually: COVID-era challenges included nurturing relationships and accountability across generations—some sellers grew up on Zoom, others with in-person interactions.
- "How do you build not just a winning culture, but a team-based culture?" – Matt Nolan (04:18)
- Board management: Board interactions are a unique, under-discussed challenge for new CROs, requiring mentor support and deliberate trust-building.
2. Transition from Sales Tactics to System Leadership
Timestamp: 07:03–08:55
- Evolving from deal involvement to systems thinking: As revenue grows, CROs shift away from direct deals toward leading complex operational systems (hiring, modeling, legal, etc.).
- “You’ve really got to hire really good leaders underneath you who can manage the customer relationships... you have to do a lot more kind of table setting.” – Matt Nolan (07:47)
- Taking on organization-wide “big rocks” no one else can move (e.g., legal function overhaul).
3. Managing Culture and Driving Change
Timestamp: 09:00–14:53
- Balancing “same before different”: Learn the business and honor what works before shifting strategy.
- Authenticity and transparency win hearts and minds, especially with legacy employees.
- Hybrid leadership teams: Avoid “clean slate” overhauls; blend legacy and new talent for stability and fresh perspective.
- Cultural transformation metrics: Internal engagement survey improved from ~70% to 91% favorable, reflecting successful cultural buy-in.
4. Team vs. Me: Committing to a Team-Based Culture
Timestamp: 15:31–17:40
- Deliberate culture-building: Leadership team book clubs, exercises, and calibration (e.g., reading The Advantage by Patrick Lencioni).
- Career development and promotion as team goals: Leaders evaluated on their ability to develop and promote talent, not just hit numbers.
- “If you miss the number by 5%, but I’m promoting half your team... I can take that hit.” – Matt Nolan (16:32)
- No tolerance for “jerks”: The hiring process prioritizes team-oriented DNA over individual achievement.
5. “Culture is What You Tolerate”
Timestamp: 17:56–21:30
- Accountability for performance and behavior: Leaders are responsible for addressing persistent underperformance to protect organizational health.
- “Sometimes you let people go and it’s the best thing that can ever happen for them.” – Matt Nolan (18:33)
- Solution-based vs. excuse-based culture: No tolerance for recurring excuses; relentlessly solution-focused.
6. Recruiting as the #1 Leadership Priority
Timestamp: 21:30–34:28
- Recruiting pipeline is the job: Leaders own their people pipeline as much as deals pipeline.
- “Pipeline is recruiting. Pipeline is like your number one job... our ICs need to be doing PG all the time, and our leaders need to be doing PG around people.” – Matt Nolan (22:31)
- “There’s nothing better [than] hiring that rep I just talked about and getting him into our org than winning a new logo.” – Matt Nolan (22:57)
- Never stop recruiting: Keep warm relationships with high performers, recruit top talent even when there’s no open headcount.
- Leaders teach recruiting down the line: True CROs teach frontline managers how to source, evaluate, and land talent.
7. Sourcing Top Talent (and the Fallacies of Resume Review)
Timestamp: 34:29–59:51
- Sourcing strategies:
- Relentless LinkedIn searches—3x/day minimum.
- Tap networks, backchannel references, and role-specific hunting (as soon as a respected leader leaves a competitor, investigate their teams).
- Exponential impact of recruiting top performers and leveraging their networks ("packs").
- Structured “recruiting standups” and cross-team sessions to brainstorm candidates together.
- Use every touchpoint for recruiting—even reference checks become recruiting opportunities.
- Recruiting mindset: Always be open to opportunity, build loyalty by helping place candidates elsewhere when you can’t hire them.
- Teaching talent recognition: Internal group exercises to review “blinded” resumes, debate and diagnose traits of top performers, and ensure everyone knows what “great” looks like.
8. Selling the Opportunity
Timestamp: 50:54–54:58
- Recruiting is sales: Leaders must learn (and teach) how to pitch the opportunity persuasively; not knowing how to sell the role is a common failure mode.
- “It’s not the... list of interview questions... there are tactics and strategies to interviewing and recruiting... you’ve got to sell the opportunity to top talent.” – Matt Nolan (52:11)
- Audible-ready exercises: Role-play “Why work here?” interviews; leaders must deliver conviction and specificity.
9. Aggregate Talent Math: Hiring Early & Enablement Excellence
Timestamp: 41:18–44:36
- Macro math matters: Every month of open headcount across a large org aggregates into millions in lost revenue opportunity.
- Hire early and invest in enablement: Shorten ramp times to “beat the math” for hitting plans quarter after quarter.
10. Culture + Recruiting = Dynasty
Timestamp: 61:21–62:49
- Sports parallels: Building a dynasty—like national-champion coaches—hinges on relentless recruiting, then fortifying culture around your best talent.
- “The thing... agreed on is like, you don’t have to morph your culture to everybody... people are going to opt out or opt in from that culture and that’s okay.” – Matt Nolan (62:32)
Notable Quotes
-
On Leadership Responsibility:
“Everything you say and do is being watched and internalized.”
— Matt Nolan (02:54) -
On Team vs. Me:
“I’m judging you based on how many people we can promote off your team. If you miss the number by 5%, but I’m promoting half your team, I can take that hit.”
— Matt Nolan (16:32) -
On Recruiting Relentlessness:
“There’s nothing better... than hiring that rep I just talked about and getting him into our org than winning a new logo. Because... the multiplicative effect of having like great people... once you see it, you can’t unsee it.”
— Matt Nolan (22:57) -
On Board Management:
"You're gonna spend that first six to nine months proving yourself right."
— Matt Nolan (09:02) -
On Pipeline Math:
“As a CRO, you just lost your job... You are the aggregation of all of their mistakes, which they don’t really pay a high penalty for.”
— John McMahon (43:44) -
On Cultural Accountability:
“Culture is what you tolerate.”
— Matt Nolan (04:06) -
On Recruiting as Universal Leadership DNA:
“Pipeline is recruiting. Pipeline is like your number one job.”
— Matt Nolan (22:31)
Memorable Moments & Advice
- A-Players Run in Packs: If you hire one, immediately ask them who else is great in their network or who was the hardest to compete against. Bring them in too. (27:08)
- Backchannel as Sourcing: Use reference checks and backchanneling not just for verification, but as active recruiting. (50:07)
- Promote “Recruiting Mindset”: Leaders should always have “three openings” in mind, recruit ahead of plan, and place promising candidates even when there's no immediate vacancy. (33:15, 38:19)
- Facilitate Talent Recognition: Use blinded resume exercises in leadership meetings to align everyone on what "great" actually looks like. (55:47)
- Selling the Opportunity: Being audible-ready to pitch “why here?” is mandatory for every leader; the candidate judges the opportunity through your passion and conviction. (53:05–54:29)
- Talent & Product Flywheel: Recruiting delivers short-term results; culture sustains long-term performance akin to building a sports dynasty. (61:21–62:49)
Timestamps for Key Segments
- [02:17] — Lessons learned: first-time CRO, difference in PE vs. VC
- [04:06] — “Culture is what you tolerate”
- [07:03] — Evolution from frontline sales to system leadership
- [09:00] — Board management, gaining trust
- [14:20] — Cultural engagement metrics
- [15:31] — Team vs. Me: leadership exercises, promotion mindset
- [17:56] — Accountability: dealing with underperformers
- [21:30] — Relentless recruiting as core DNA
- [27:08] — Sourcing A-players via networks
- [34:29] — Constantly recruiting and backchannel hiring
- [41:18] — Importance of hiring ahead and enablement
- [50:54] — Selling the opportunity in recruitment
- [55:47] — Resume review exercises for leadership calibration
- [61:21] — Building a dynasty: sports parallels, recruiting + culture
Final Takeaway
If there’s one lesson from this episode: Recruiting is the single highest-leverage activity for revenue leaders—it surpasses closing deals, managing the board, or operational fixes. Relentless, disciplined recruiting at every level, reinforced by a healthy, team-centric culture, is the foundation for both rapid growth and eventual dynasty status.
“You can be bad at everything. If you’re great at recruiting, you can cover for a lot of sins and fill those in in other ways, but hard to do the inverse.”
— Matt Nolan (65:14)
End of Summary