OUR Founder


          “I’m in the business of ideas, information and connections.”

Ingrid Riley is CEO of ConnectiMass.

A big believer in #DigitalCaribbean and its limitless possibilities for the Region, Ingrid is a Private Sector Organisation of Jamaica (PSOJ) 50Under50 Business Leader Gamer Changer Awardee + TechLink Game Changer Social Entrepreneurship Awardee. She was  awarded for her work in kick starting Jamaica’s Tech Startup Community in 2007 and pioneering work in helping the development of the Caribbean Startup Ecosystem.

Ingrid has been a Dow Jones syndicated and Newspaper technology columnist and has written over 1,000 articles on topics ranging from Startups, Startup Ecosystems, Social Media, Digital Culture and Trends.

She currently serves as Board Chairman of Startup Jamaica, the Technology Accelerator, sits of Advisory Boards of organisations focused on Youth and Women Tech Entrepreneurship and is mentors a few startups annually. She’s also an award-winning Digital Strategist +Coach, award-winning Tech Blogger. Ingrid is a Speaker on Technology, Innovation,  Tech Entrepreneurship, Startup Ecosystems and Digital Culture. She is also known to be a Super Connector.

Life Ambitions

To continue to do what I love to do each day and that it leaves a little dent in the universe, leave the Caribbean especially, a better place than I found it – and that it all makes a significant and positive impact on the lives of people it all touches. To continue to live my life on my terms, having time, money and travel freedom, then to gracefully exit of a very, very old age with a smile on my face, knowing that I lived my very best life.

Challenge the Status Quo, Always.
Be mindful of your intentions.
Meditation solves almost everything. 🙂

An Entrepreneurial + Tech Industry Snapshot

  • Been in the Internet/Tech Space since the mid 1990s
  • Been blogging since 2005
  • My first startup published Jamaica and the Caribbean’s first Internet Guide – iGuide Jamaica
  • Co-founder of the Caribbean’s first online advertising network – Caribclix.
  • Launched and ran a niche social network and learnt a lot.
  • Worked for an American dot com in the mid 90s, even owned stock but then the bubble happened.
  • Co-founded one of the most successful web development agencies in the Caribbean- Dutchpot Interactive and only one in the Caribbean led by two women.
  • Launched the Caribbean’s first and longest running Technology Blog in 2005 – SilconCaribe.com
  • Angel invested in 3 startups in the early 2000s, and that was an adventure.
  • Kickstarted the Jamaican Tech Startup Scene in 2007 with the Caribbean’s first meetup Kingston Beta, followed by the Caribbean’s first tech entrepreneurship conference in 2011 – Caribbean BETA.
  • The only digital marketing strategist in Jamaica that’s crafted a digital blueprint for an entire country (Jamaica Tourist Board’s Visit Jamaica Brand), hired, trained and led a team to execute.
  • SXSW Startup Accelerator Event Board Member

A Few Awards

  • Named a Private Sector Organisation of Jamaica/Jamaica Gleaner 50 Under 50 “Game Changer “ Business Leader Awardee in 2012
  • TechLink Game Changer’s Award for Social Entrepreneurship.
  • Named by CaribJournal.com, one the Caribbean’s 25 Most Interesting newsmakers for the year who made a difference in the region.
  • Won Blog of the Year and Best Technology Blog by the Jamaican and Caribbean Blog Awards.


  • I LOVE to travel and do it a lot.
  • Even as my iPad is full of e-books, nothing gets me excited like a bookstore with a great stock of international magazines and unique non-fiction and poetry.
  • I used to be a performance poet.
  • I once owned a bar and was a successful Party promoter.
  • I love cafes for hot chocolate and working.
  • I love Red Wine.
  • I am a yogini.
  • I recently got back into bicycling, a long time love.
  • I have a thing for Vespa Scooters

My Social Networks of Choice

Facebook – I am on often.
Twitter – I am part firestarter and part curator.
Instagram– I use this as my space of inspiration
LinkedIn – I am not there much
FourSquare – I use this a lot when traveling
Quora– I barely use this, though I think I should be there more.
Google+ – I am not there much at all.
Klout – I like to see my score every now and again

Contact me

ingrid at connectimass.com.

Keynote Speech + Fireside Chat at Black Tech Week, Miami Florida

Featured in a SiliconValley TedxTalk by Gary Whitehill

Topic: Stop making excuses. Create your own reality:



Ingrid was featured in a SiliconValley TedxTalk by Gary Whitehill