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 take my practical, proven approach to sales and marketing outside 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 and 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.
Hear what some of my clients and colleagues have had to say about me after working together on various projects and in different roles.
"James is one of the best experts I've met. Extremely proactive, results driven and keen to innovate. Want to test all the newest techniques and methods in marketing your idea? James is your expert! Outstanding knowledge of the market, best experiences in the field, and excellent people skills!"
"James is extremely diligent and detail oriented. He excels at being able to look at things on both a macro and micro scale. He's also very talented when it comes to managing people, teams, and other moving parts within a business. More importantly, he's not afraid to roll up his sleeves and apply his talents, or to expand his horizons, especially with new technology and systems."
"James has an endless thirst for knowledge and willingness to educate himself in any field or technology there is. His superpower is finding brilliant solutions in unusual places. As a manager he is not only amazingly well organised, he is also great at instilling confidence in his coworkers and encourages them to think and offer ideas. Pair all this with his sense of humour and we have a winning combination!"
"James is wise and intelligent far beyond his years. He is one of the most respected men I have ever personally met. James will gladly put others ahead of himself without any hesitation or remorse. If I ever had to get a team together for any project, James York will always be my first choice due to his personality, work ethics, and goal oriented mind. There are few and far between like James. Anyone that has an opportunity to work with him should feel privileged!"
"My team and I had the opportunity to work for James earlier this year on a new product introduction. We were constantly amazed by the insights and vision James contributed to the project. His ability to work collaboratively and inspire a diverse team of specialists helped us all overcome challenges and meet our critical objectives."
"James is passionately devoted to whatever he puts his mind to and is someone who enjoys the rare of quality of being equally comfortable with, and adept at, supporting the team or taking the lead. He is wise, extremely well organized and fun to work with. I learned a lot from him during our time together at Fits.me, and it was a pleasure from start to finish! If you are looking for a bright mind, with the ability to both see what needs to get done, and then push forward to make sure it happens, James is your man and I would highly recommend him as a solid and dedicated addition to any team."
"As a fellow senior manager, James was a pleasure to work with. Reliable, energetic and extremely detailed oriented, his skill set would easily lend itself to many industries. James was particularly successful in seamlessly integrating and utilizing more modern technologies into our operations."
"James has the special ability to connect business with tech, keeping an overview from the top and having knowledge of each technical aspect involved. He is able to be explicitly clear as to the needed scope and desired outcomes, while understanding and taking into account both the limitations and flexibilities of the systems at play. James wasn't just interested in the end result, but was also eager to know how it was built so he could contribute to the solution. His uncanny ability to dive into the details to understand the root of an issue and then turn it inside out helped us reach some innovative solutions very quickly. And he does it all with a great sense of humor! I'm looking forward to working with him again."
"James is a creator. Driven, passionate about what he does he is pretty much unstoppable. He is a hard worker, analytical and has great communication skills. I highly recommend him for building something up."
"In 2005, I was teaching the Series 7 part time and was James's teacher. James was a quick study and excellent student, and he crushed the test. At the time, anything in the 70's was passing and an admirable score, James scored in the 90's on a very very difficult test.
He is easygoing and a credit to anyone who teams up with him."
"James is the perfect person to work with. He is not only devoted to his work, but also knows how create pleasant associations with his colleagues. James is a man of his word and is one of the most organized people I know. His even temperament makes him a pleasure to work with and I have enjoyed my relationship with him all along. I wish everyone had his work habits and attitude."
"James brings a surprisingly large variety of skills to the table. From a painstakingly good eye for detail, to having the nerve to actually push things through while maintaining good rapport and his awesome sense of humor, he could run a startup and lead it to success or just as easily guide a client's hand to do the same. And he wouldn't even think anything of it. He'd just call it a good day's work. If you have the chance to work with James; do."
"James is a driven problem solver that has the rare combination of both big picture thinking and the ability to manage logistics and small details."
"James is an inventive, thoughtful personality who is not afraid to try new and unbeaten paths to achieve results."
"James is a very driven and dedicated person. He sees the right opportunities and works very hard to deliver the best results."