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Matt Di Paola  - IDEABOOST. Toronto, ON, CA

Matt Di Paola Matt Di Paola

Managing Director, Digital Innovation & Sid Lee Media, Partner | SID LEE

Toronto, ON, CANADA

Matt Di Paola is a mentor for IDEABOOST.



With 20 years of agency experience, Matt brings a culture-first leadership style to organizations with a focus on innovation, entrepreneurialism and digitally led thinking. Having worked across the spectrum of communications services, including PR & event marketing, traditional advertising, CRM, digital, UX and media, Matt applies that breadth of experience and advises clients holistically and objectively on their marketing problems.

He has also worked across key verticals, including finance, consumer packaged goods, travel & tourism, technology, retail and automotive. These clients have allowed him the opportunity to work at the Global level, as well as service specific markets, including Canada, US, Hong Kong & Australia.

His focus on the work has helped 3 different agencies win Agency of the Year as well as Cannes Lions, Best in Shows at the CMAs & FAB Awards, and LIAAs along with many other local awards. His entrepreneurialism has helped digital & media agencies evolve and introduce new Comms Planning models (across Paid, Owned & Earned), Business Intelligence & Analytics, Branded Entertainment, Mobile & Social Strategy specialties.

Matt helps facilitate connections between start-ups and brands. He also works with start-ups on their brand story, brand purpose and design.

Industry Expertise (3)

Research Training and Development Education/Learning

Areas of Expertise (4)

Digital Marketing Integrated Marketing Digital Strategy Digital Media

Accomplishments (3)

Digital Online Design, Cannes Lion - Silver (professional)


Silver Cannes Lions award for Digital Online Design for the Massey Lectures iPad app created for House of Anansi Press Inc.

Media Agency of the Year - MediaCom Canada (professional)


Awarded by Strategy Magazine

Digital Agency of the Year - Tribal DDB Canada (personal)


Awarded by Marketing Magazine

Education (2)

Humber College: Certificate , Public Relations Post-Graduate 1995

Western University : B.A., Political Science 1993

Affiliations (5)

  • Cannes Lions
  • Colleges Ontario
  • Strategy Magazine
  • Digital Launch Pad
  • Fundraising Committee

Event Appearances (2)

Big Data, Big Brands, Local Insights

Big Data, Big Brands, Local Insights  SXSW


Show Me the Money! : Financing + Distributing the 360 Property

Merging Media  Vancouver, BC.