Roadmap
Malpractice

How Missed Signals Transfer Risk to Go-To-Market Teams

T.J. Prebil

June 2026

Roadmap
Malpractice

How Missed Signals Transfer Risk to Go-To-Market Teams

Every product initiative is a bet. When those bets miss, the cost does not stay in the product team. It transfers downstream to the people who have to sell it, demo it, position it, and retain customers despite it.

By T.J. Prebil

About the Book

Roadmap Malpractice examines how product decisions create momentum or friction for go-to-market teams, what it costs when misalignment goes undetected, and why the signals to make better decisions already exist inside most organizations.

Most companies treat roadmaps as execution artifacts. Plans for sequencing work, tracking delivery, and communicating priorities. But roadmaps operate at a higher level. They shape how products are explained, sold, implemented, and defended in the market. Every roadmap decision allocates risk to the teams that carry it forward.

When roadmaps are built without adequate market signal, that risk does not disappear at launch. It moves downstream. And the people who absorb it are rarely the people who made the decision.

This book is not anti-product. CPOs have one of the hardest jobs in enterprise software. It argues that there is a source of strategic intelligence most product organizations are not fully tapping, and that the cost of ignoring it compounds in ways most leadership teams do not see until it is expensive to fix.

What's Inside

Eighteen chapters across four parts, built from patterns observed across multiple venture-backed and PE-backed B2B SaaS companies.

Part I

The Problem

What roadmap malpractice actually is, how to recognize it, and why it occurs even in well-run organizations with talented teams.

Part II

The Consequences

How risk transfers downstream when products ship, what that costs economically, and what is at stake for the people who carry it.

Part III

Better Signal

The limits of customer feedback, the signals organizations are not listening to, and a framework for understanding which signals matter most.

Part IV

The Solution

What momentum actually looks like, how leadership accesses it, and what changes when organizations treat go-to-market teams as a source of strategic intelligence.

About the Author

T.J. Prebil has spent fifteen years in go-to-market roles across multiple B2B enterprise SaaS companies, from venture-backed startups to PE-backed platforms. He has worked in marketing, product marketing, and sales enablement, giving him a front-row seat to how product decisions land once they reach the market.

He is the founder of Emergent Insights, where he helps companies assess whether their product strategy is creating momentum in the market and identify where teams are misaligned before it impacts growth.

Get notified when the book is available

Be the first to know when Roadmap Malpractice is available for purchase or download.

No spam. One email when the book launches.