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We reported that Simon Jennings had left his position at Olive Media to become the Chief Revenue and Digital Officer at Postmedia Network, something that surprised some, and left a few others with a “but why feeling,” as Postmedia Network has struggled since its inception to get its digital game on.

I recently ran into an someone who worked with Simon in the past, we stuck a conversation about the changes in the industry and they shared the following comment, “I’d follow Simon into battle anytime. He knows how to manage a team, share his vision and get things done.”  Knowing a number of other individuals who have worked for Simon over the years, it is not surprising to hear that said about him.  His track record speaks for its self as he’s built great companies and teams everywhere he has been,  he’s has earned the nickname, Simon “General” Jennings.  While at Olive Media, with the help of his team, they created a strong brand within the advertising industry, and there is no doubt that we can expect some big things in his new role. Here are 4 things that we expect to see:

  1.  There will be a kick ass Postmedia Network party sometime this year, probably in the fall
  2. Postmedia Network will be on a hiring spree – a number of people will follow Simon over to Postmedia, he’s a “General” and people want to work for a leader, his track record shows as people have followed him from Yahoo! Canada to Olive Media; no doubt his inbox is filling up with resumes from other people in the Canadian advertising industry wanting work at Postmedia
  3. Postmedia Network will buy at least 1 start up before 2012 is done – although he has either run or employed by a few companies, deep down Simon has an entrepreneurial spirit, he also recognizes the opportunity for a larger company to acquire an integrate startups, Paul Godfrey, President & CEO of Postmedia Network, has been on the look out to acquire more startups
  4. Postmedia’s online advertising sales will start to see an increase, perhaps sometimes around mid-2012

As you’ll see from the photos below from two of Olive Media’s annual parties, Simon has a flare for doing it up big – but he does it on the playing field and in the boardroom.

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About the author 

Dave Forde

Dave “The Connector” Forde is a 20-year veteran of the Canadian marketing, PR, and tech industries. He is the founder of The Connected One network, including industry news sites Canadian Ad Insider and PR In Canada, and serves as a strategic business advisor. Connect with him on LinkedIn and X.


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