Ep 8: The Hard Truth About Going Up-Market (and Why Most Teams Fail) From Karl Ortmann's Revenue Problem Solvers Podcast

In this special episode of GTM by the Numbers, we’re flipping the script. Instead of hosting a guest, we’re rerunning Brandon Redlinger’s appearance on the Revenue Problem Solvers podcast with host Karl Ortmanns.

The conversation centers on one of the toughest GTM challenges out there: moving up-market. Brandon shares battle-tested stories from his time leading marketing at high-growth SaaS companies, including both painful lessons and breakthrough wins when transitioning from mid-market to enterprise.

You’ll hear why a single big logo isn’t proof of readiness, how to align product, marketing, and success teams for enterprise buyers, and why hiring experienced talent in the right vertical can make or break your motion.

What you’ll learn in this episode:

– Why closing one big account doesn’t mean you’re “enterprise”

– How to know when it’s actually the right time to move up-market

– The critical role of product readiness and customer success in scaling to enterprise

– Why focus beats chasing every vertical, and how Brandon found success with healthcare

– The importance of hiring for expertise instead of retraining your best mid-market sellers

This is a must-listen for GTM leaders eyeing larger deals and wondering what it really takes to scale successfully.

Connect with Karl Ortmanns at https://www.linkedin.com/in/karlortmanns/

Connect with Brandon at linkedin.com/in/brandonredlinger

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