Dynamic Decisions Podcast

Jason Jackson has spent more than two decades walking into companies that have built something real and then gotten stuck. As founder and operating partner at Redwood Ridge Strategies, he specializes in diagnosing the operational constraints that prevent growth-stage SaaS companies from scaling past product-market fit. And more often than not, the constraint has a title: Founder.

In this episode, Jason joins Teasha Cable to unpack what he calls "founder drag," the invisible pattern where the very behaviors that built a company begin to cap its growth. He shares real examples, including a founder answering customer emails at 1am with the wrong name on them, and explains how he helps leaders see the bottleneck they've become, then systematically build the systems and team capability to grow without them.

The conversation covers:

• How Jason used an LLM-based support system at Suzy to cut $1.5 million in annual overhead, while simultaneously moving team members into higher-value, higher-growth roles instead of eliminating their jobs.
• Why the per-seat SaaS pricing model is losing relevance and how to gather the willingness-to-pay data you actually need to build a pricing philosophy that fits today's market.
• The difference between sales-led and product-led growth, and why PLG demands a fundamentally different relationship between your product and your customer.
• What sustainable consulting actually looks like, including why Jason deliberately builds clients who don't need him anymore.

If you lead a growth-stage company, or advise one, this episode will reframe how you think about where your real constraints live.