About Jeffrey Shear

Two Decades of Enterprise Technology Leadership, Now Focused on Growing Businesses

Bringing the same rigor and strategic thinking applied in boardrooms at major institutions to businesses that are earlier in their growth trajectory.

I'm Jeffrey Shear. For more than twenty years, I've served as a trusted advisor to executive teams and boards navigating technology strategy, digital transformation, and organizational growth. My work has spanned financial services, wealth management, healthcare, and professional services — with clients including JP Morgan Chase, Citibank, Fidelity Investments, Prudential, AIG, and Siemens.

Alongside this advisory work, I've also held direct operating leadership roles — including serving as Chief Information Officer for a growing professional services firm, and as Fractional CIO for a company where I helped drive 500% revenue growth through digital modernization. In another engagement, I reduced operating costs by 50% by modernizing outdated infrastructure and eliminating manual inefficiencies.

What I've observed: the organizations that most need this caliber of strategic guidance are often the ones with the least access to it. Small and mid-sized businesses face the same fundamental challenges as large enterprises — fragmented data, disconnected systems, and unclear paths for adopting new technologies like AI — but rarely have the internal resources to address them, and can't always justify a full-time senior executive to do so.

I founded this practice to close that gap: bringing the same rigor and strategic thinking I've applied in boardrooms at major institutions to businesses that are earlier in their growth trajectory, delivered in a way that's practical, efficient, and appropriately scaled.

Guiding Principles

  • Technology should serve the business, not complicate it
  • Every recommendation should be understandable to the people who have to act on it
  • Sound advice is honest advice — including, when warranted, recommending against a purchase or project
  • Businesses of every size deserve access to disciplined, experienced strategic guidance

Background

  • 15+ years advising executive teams on technology, data, and transformation strategy
  • Former Chief Information Officer, Wiss & Company
  • Former Co-Founder & CEO, LicenseStream, grown to market leadership in digital content licensing technology
  • Advisory experience with JP Morgan Chase, Fidelity Investments, Citibank, and Siemens, among others
  • Data Science Certificate, Cornell University
  • Based in Ridgefield, Connecticut, serving clients nationwide
Ridgefield, Connecticut — serving clients nationwide
Jeffrey Shear — Senior Technology Executive

Let's work together

Whether you need a fractional executive, a strategic advisor, or a thought partner — I'd welcome the conversation.

Get in Touch