About Dean Waye - Winston Writes

About Dean Waye

B2B Positioning & Marketing Strategist

Specializing in challenger brand strategy and category disruption for CMOs, CROs, and private equity-backed technology firms.

Market Leadership Through Upstream Problem Solving

Dean develops asymmetric messaging and go-to-market (GTM) strategies that create decisive sales momentum. His core philosophy is that market leadership requires solving problems upstream.

He challenges the formulaic marketing that causes most B2B companies to blend in, focusing instead on finding a unique, defensible market position rooted in challenger thinking.

Asymmetric Advantage

Identifying positions competitors cannot replicate

Category Disruption

Breaking through market noise with decisive messaging

Enterprise Focus

Messaging that engages sophisticated B2B buyers

Sales Momentum

GTM strategies that drive measurable results

The Methodology

01

AI-Driven Market Research

Proprietary analysis of customer language, competitor claims, and broad industry narratives to uncover hidden market insights.

02

Divergent Thinking & Analysis

Rigorous root cause analysis applied to market datasets to identify gaps, whitespaces, and differentiation opportunities.

03

Strategic Messaging Framework

Development of foundational 'source copy'—a strategic messaging framework that guides all sales and marketing communications.

Enterprise Experience

Global Sales Leadership

Nokia & Openet

Top-ranked Global Sales Director with deep experience in enterprise environments. Learned firsthand what messaging engages sophisticated enterprise buyers in high-stakes deals.

Complex Problem Solving

Kronos

Project Manager consistently ranked in the top 2% of 105 PMs for turning around distressed projects. Developed expertise in complex problem-solving and strategic thinking.

Ready to Break Through the Noise?

Transform your B2B marketing with asymmetric messaging and challenger brand strategy that creates decisive sales momentum.

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Free: Get Inside Customers’ Heads

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