Bill Mason

I am a Go-To-Market (GTM) executive and revenue leader with nearly 30 years of experience introducing emerging technologies, complex cloud platforms, and high-margin professional services into new markets and unmapped territories.

My career spans the full growth spectrum: from early stage startup execution to driving multi-million-dollar enterprise sales strategies at Google, Oracle, Hewlett Packard Enterprise (HPE), and Sun Microsystems.

I advise founders, CEOs, and growth-stage tech companies on transitioning from early traction to predictable, enterprise-grade revenue engines. I specialize in helping B2B software and tech services firms navigate complex enterprise sales, attach high-margin professional services to platform sales, and scale GTM operations efficiently.

Primary Areas of Advisory Expertise
Go-To-Market Strategy & Expansion: 0-to-1 market entry, new territory launches, enterprise account acquisition, and GTM playbook creation.

Services attachment & Portfolio Strategy: Structuring, pricing, and attaching high-margin professional services to SaaS and infrastructure sales.

Complex Enterprise Sales & Deal Structuring: Navigating long sales cycles across Healthcare, Supply Chain/Logistics, Financial Services, Higher Ed, and Public Sector.

Infrastructure & Modern Workloads: Strategic sales guidance across Multi-Cloud (Google Cloud, AWS, Oracle), Big Data Analytics, modern AI/ML initiatives, and core enterprise workloads (WMS, TMS, ERP).

How I Can Help Your Business:
Advisory Board Member: Providing recurring strategic oversight on GTM direction, sales playbook development, and enterprise pipeline progression.

Fractional GTM Strategic Advisor: Partnering directly with CEOs and Founders to audit sales engines, refine value propositions, and train sales teams on enterprise-level deal execution.

Strategic Mentor / sounding Board: Guiding tech-focused founders who need experienced commercial leadership without the overhead of a full-time VP of Sales.

Preferred Board & Advisory Preferences
Target Company Stage: Early-Stage (Seed to Series A), Scale-ups, and Mid-Market IT Services / Systems Integrators ($2M–$25M ARR).

Engagement Type: Advisory Board seats, Monthly Retainers, or Specific GTM Strategy Sprints.

Geographic Focus: Open to remote advisory globally.