The Caliber Show
The Caliber Show
Chris Orlob, CEO, Caliber
The 5 Steps to POV-Led Outbound | Kyle Coleman, Global VP Marketing ClickUp
49 minutes Posted May 4, 2026 at 11:30 am.
0:00
49:52
Download MP3
Show notes

Kyle Coleman has spent 15 years architecting outbound motions that don't rely on volume - first as the founding SDR at Looker, then building Clary's outbound engine from $15M to nearly $150M in revenue, and now as Global VP of Marketing at ClickUp.


In this conversation, Chris and Kyle unpack the difference between personalization (which is now table stakes and largely useless) and a real point of view - the kind that makes a CRO stop scrolling and actually reply.


Kyle walks through the exact 5-step framework he's used to train SDR teams on POV-led outbound, why "signal monitoring" without interpretation is just dressed-up spam, and how he scaled this approach at Clary to triple qualified pipeline while sending 25-30 emails a day instead of thousands.


If you're a sales leader watching your team's reply rates collapse under the weight of AI-generated noise, this episode is the antidote.