Pilot, Prove, Scale: How CMOs Lead Transformation

If you’re not transforming, you’re getting left behind. That reality makes transformation anything but presto change; it’s a mindset shift, sustained motion, and a clear “why” your people can see themselves in.

To turn that into visible progress while keeping the ship pointed at a destination the business recognizes, Drew brings together Chris Pieper (ADP), Putney Cloos (Bombora), and David Levy (Foundever) to share how each leads transformation across differently scaled organizations. From making progress visible to earning belief across the org and sustaining momentum through the messy middle, they show how change takes hold.

In this episode: 

• Chris pilots with sales champions, proves pipeline impact, and turns small wins into momentum. 

• Putney makes the case for change, maps “scrappy to industrial strength” milestones, and scales what works. 

• David runs parallel lanes to protect the core while building the future, aligning his org to work ambidextrously.

Plus: 

• How to make progress visible with simple roadmaps and real milestones. 

• How pilots, quick wins, and pipeline proof bring sales along. 

• Why stopping low-value work frees resources for what matters. 

•  What to hire for in ambiguity: people who try new things and move fast.

Tune in if you are steering big change and want practical ways to show progress, win belief, and keep momentum through the messy middle. 

Renegade Marketers Unite, Episode 491 on YouTube 

Resources Mentioned 

• CMO Huddles 

• Past episodes mentioned 

• • Chris Pieper on Product Launches 

Highlights

• [1:42] Chris Pieper: Mindset over mechanics 

• [2:58] Winning sales through proof 

• [5:07] How pilots turn into org-wide change 

• [9:16] Putney Cloos: Transformation needs honest expectations 

• [11:03] From scrappy to industrial strength 

• [14:39] Validate fast then scale 

• [17:49] David Levy: Balancing now and next in transformation 

• [19:37] The hard part of proving transformation 

• [22:30] How marketing builds transformation pressure 

• [25:41] CMO Huddles: Your unfair marketing advantage 

• [29:16] Signals every CMO must spot 

• [33:32] Transformation needs vision and milestones 

• [36:14] What AI unlocks beyond efficiency 

• [43:34] Advice for CMOs leading through transformation 

Highlighted Quotes  

“Transformation isn't just about changing approaches. It's really about shifting mindsets as a key factor of success."— Chris Pieper, ADP 

“Scrappy to industrial strength. We're in the scrappy mode. So it means we're piloting it, we're doing it in sort of a dirty way, but we're not letting perfect get in the way of good enough."— Putney Cloos, Bombora  

“Transformation is not a campaign, it's not a value proposition, it's not a brand promise. It's an act of leadership."— David Levy, Foundever 

Full Transcript: Drew Neisser in conversation with Chris Pieper, Putney Cloos, & David Levy