The Elusive Digital Marketing Ninja: An Upside Foundation Member Dinner - Upside Foundation of Canada

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The Elusive Digital Marketing Ninja: An Upside Foundation Member Dinner
December 1, 2016


An evening for Upside members to learn and connect.

At our Member Breakfast in August, two key insights came out of our discussion. Our members are looking for more opportunities to connect with each other, and one of the most common challenges being faced is finding a ‘digital marketing ninja’ to support business growth. Thus was born the idea for our latest event: a dinner for our members on November 2 focused on digital marketing.

Caleb Rubin, Co-Founder & Chief Marketing Officer of Kahuso, kicked off the conversation sharing his insights into the digital marketing world. He shared an overview of what digital marketing really is, the types of skills to look for when hiring a person to fill this role, and the key steps to developing and implementing an effective digital marketing strategy.

Caleb had many insights into digital marketing

“Marketing has changed from a monologue to a dialogue. Digital marketing is effectively managing that conversation”

Some useful tools to manage that conversation include: Buzzsumo, Mention, Hootsuite, HubSpot, Google Analytics, SuperMetrics, Lucky Orange, Quora, Outreach Ninja.

Key reasons why digital marketing fails:

  • There’s no strategy (persona mapping; which conversations are you going to own)
  • Talking about what you do vs why they should care (check out Simon Sinek’s TED talk on this concept)
  • Not having the right lens (has to be about growth- maniacally moving people through that funnel)

Great marketing does 1 of 4 things*:

  • Amplifies dreams
  • Alleviates fears
  • Puts them on safe ground
  • Allows you to throw rocks at your enemies

*Principles derived from Ray Edwards

Key elements of a great digital marketer today:

  • Brand strategist
  • Data scientist
  • Geeky nerd — like to get your hands dirty with tools & experiment
  • True north = growth — maniacal about growth and learning

You will need each of these things more at different stages at your startup. Because it’s virtually impossible to find one person who embodies all of these, Caleb suggests hiring someone who is maniacal about growth and learning, and supporting them with a coach who can help them with the brand elements.

“The idea of marketing today is not that you know but that you know how to learn — failing is learning, and you need to continue to fail in marketing to learn and grow”


By popular request, the full talk can be viewed online by Upside Foundation members here. Reach out to Jen if you do not yet have the password.

A huge thank you to Caleb Rubin & Michael Carter, Co-Founders of Kahuso, for lending their expertise to Upside Foundation members. In addition, they have generously offered one free search on Kahuso to members (a $1,000 value).

Interested in participating in similar events in the future? Take the pledge today to ‘share the upside’ and reap the benefits of being a company that cares!

Written by Jen Couldrey, Foundation Manager of the Upside Foundation.


Kahuso is a platform connecting accomplished executives and professionals with companies for contract, advisory and board opportunities. Kahuso is committed to giving back to the community, and is a proud member of the Upside Foundation.


The Upside Foundation of Canada is a registered charity. The Foundation provides an innovative corporate philanthropy platform to help Canadian startups and high-growth companies “Share the Upside”. Since startups’ cash is scarce, as is time, the Foundation makes charitable giving quick, easy and cash-free.

The model is powerful: Earlier-stage and high growth private companies pledge stock options or warrants to the Upside Foundation. When the company has a liquidity event (e.g., IPO, acquisition), the Foundation monetizes the options and donates the proceeds to registered Canadian charities selected by the donors (and approved by the Foundation).

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