Positioning That Sales Actually Uses with Jennifer Sillars

Every growth-stage company eventually runs into the same problem.

The positioning sounds great in a messaging deck… but it doesn’t show up in sales conversations.

The story feels clear internally, yet deals stall, messaging gets distorted, and customers walk away confused about why your product actually matters.

In this episode of Marketing Pack Leaders, host Josh Porter, founder of Thunderwolf Consulting, sits down with Jennifer Sillars, product marketing consultant and founder of Cosmic Strategy, to unpack why this happens and how to fix it.

Jennifer has spent more than a decade helping B2B technology companies turn complex features into buyer-centered value. With experience including roles at Arm and deep consulting work with startups and scale-ups, she focuses on positioning, messaging, and aligning go-to-market execution to revenue outcomes.

Her core belief is simple: great positioning isn’t finished when the messaging doc is written—it’s finished when sales teams use it naturally in real conversations.

This episode dives into how product marketing leaders can close the gap between strategy and execution.

What This Episode Is About

Josh and Jennifer explore how positioning often breaks down between marketing strategy and frontline sales execution.

Topics include:

• How to tell when positioning is truly sales-ready, not just marketing-ready

• The most common breakdowns between positioning strategy and real-world sales conversations