James S. York

Entrepreneur, Mentor, Marketing Technologist

A little about me


My professional life has afforded me the opportunity to work with shape-shifting robots, travel broadly, and work hand-in-hand with passionate founders and small business owners across a broad spectrum of sectors - from e-commerce to Virtual Reality and recruitment, just to name a few.

Entrepreneurial and technology focused in everything that I do, I’m known for getting things done and being able to focus on the little details without losing sight of the big picture - bridging the gap between business and tech to align vision with execution.

I cut my teeth in the business of technology working with innovative and inspiring startups throughout Europe and in New York; helping them to grow sustainably, optimize their sales pipelines and systematize their operations to facilitate productive changes in their business.

After years of working hand-in-hand with amazing startups cutting across a wide swath of industries and technologies, I had my lightbulb moment — to expand my practical, proven approach to sales and marketing beyond the tech bubble.

So in 2016, I set up Oscar Diggs Digital here at home in New York City, with a mission to help impactful businesses, innovative startups, and passionate NPOs bridge the gap between technology and human connection so their unique ideas can be transformed into extraordinary action.

I hold a degree in International and Global Studies from the NYU Tandon School of Engineering Polytechnic Institute and am an avid systems thinker. I've (briefly) been a stockbroker on Wall Street, and have managed one of the highest profile public real estate portfolios in New York City.

And while I'm now based again in New York, I've spent years living and working abroad in the small Nordic nation of Estonia, the "Silicon Valley" of Europe, where they have been discreetly driving innovation on a global scale, incubating the likes of Skype, Fits.me, GrabCAD, Transferwise, e-Residency, Starship Technologies, and many other game changers in the world of technology and startups.

With a passion for digital marketing, process improvement, cross-border business development and marketing automation, I excel at bridging the gap between business and tech and I'd love to chat.


Nice Things People Have Said About Me

Hear what some of my clients and colleagues have had to say about me after working together on various projects and in different roles.



TartuUlikoolGuest Lecturer, Digital Marketing

sTARTUp_Day_Logo_2018_smallSpeaker, 2019 sTARTUp Day


Founder & Organizer

business101Co-Founder, Lecturer