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OOH Today’s Champion —Outselling’s Bob Wolfe

3 Magical Changes for Out of Home

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Bob Wolfe is President, of OutSelling, Inc.

Bob Wolfe OOH Today Champion Proponent

OOH Today features women and men who Champion and define the Outdoor Advertising Industry.
We share the faces and stories behind the names who add a personal dimension to #Out-Of-Home (OOH).  Relationships are still an important part of #OOH and is an Industry, where the people behind the company, are as important as the company itself.

We visited with Bob Wolfe, President, of OutSelling, Inc.

OutSelling is a Chicago based company, which started started 14 years ago with OOH Inventory throughout the United States. With over 28 years experience working in OOH, Bob cut his teeth in the Industry with Whiteco Outdoor from 1990-until the sale to Chancellor Media in 1998.  Working for Chancellor until their sale in 1999 when purchased by Lamar Advertising, Bob then moved on to Clear Channel until 2003.  In 2003, he worked for Equity Office Media Network .  In 2004 he started OutSelling, Inc.  A graduate of The Ball State University, and rumored a dorm mate with David Letterman, Bob’s freshman year, Bob is Indiana born and raised, living with his wife and children in Chicago.  He adds, he is a Cubs and Bears fan throughout.  Bob has a great, self effacing, Midwest sense of humor and an infectious smile.

OOH Today’s Conversation with Bob Wolfe


BB: How did you get in the Out of Home business?

BW: I would love to say that I always wanted to work in outdoor but like probably 95% of the people in this industry, I kind of fell into it. I was working at an advertising agency and was laid off.  This was an unfortunate trend in the industry during the late 80’s and early 90’s.  Fortunately, a friend of mine worked for Whiteco Outdoor and suggested that I interview.  I remember thinking, I don’t want to sell billboards, but I went ahead and took the interview.  They offered me the job and I considered it as a good opportunity to get into more agencies and find work (basically a “job to get a job.”)  Fast forward nearly 30 years later…still looking for that big break!

BB: Nearly 30 years is quite a ‘fall into’ a career.  Obviously you love it.  What has kept you in Outdoor?

BW: The people.  And I sincerely mean this.  It’s not just the power of the medium but the people that work in it.  I don’t know how many people I have come across that have worked in this space, left and then returned.  We are like a reoccurring rash.

BB:  A reoccurring rash?  So you have some scars you have endured? What have you done in OOH you are most proud and makes you a Champion?

BW: Champion-no, proponent-yes.  I would like to think I have made an impact on providing a voice for the little guys who have good inventory/ opportunities by representing them to the big players in this space.

I have made an impact on providing a voice for the little guys who have good inventory/ opportunities

BB: As a Proponent then representing, tell us about your ‘Ah HA! Moment’ working in OOH.

BW: My first “ah ha” moment takes me back to the beginning of my career, working in local sales.  It was my first sale where I actually cold-called the customer.  They bought the program, we collaborated on the creative and we produced the vinyl.  There it was, 672 square feet (with extensions) of hard work on the street for all to see.  The payoff came when the client went out of his way to tell me how everyone is talking about “my billboard”.  He then proceeded to say, “I can’t wait to see what we do next.”  It just doesn’t get any better than that.  (OK, I lied, a big order with large commissions doesn’t suck either.)

BB:  What is the future of OOH?  Do you have a predictions or foresight to share?

BW: It will be far less personal and more programmatic, which is very sad.  I think that price points will go down as real “selling,” is eliminated and ALL inventory becomes nothing more than a commodity distinguished only by an impression number.  There will be a lot of “sellers” but very few “strategic buyers” as everything will be on-line.  While there will always be a need for sales people, they will have to be very strategic and smart about their approach to business.  Companies who instill “old school” sales strategy and tactics will die out.

BB: It is obvious you have embraced change, keeping your values, yet continuing learning and evolving with the Industry. Is there anyone you most admire or credit providing significant influence in your career?

BW: I am very fortunate to have started my career working for a very solid company that instilled good habits and a solid work ethic.  Management and ownership were instrumental on training me to sell and manage the right way.  I also credit my success to my clients who I grew up with in the industry. I learned so much from them and they taught me what it takes to make an impact when selling.  I learned what works, what doesn’t and what I need to do to get them to buy my stuff.  Very valuable, real-life training.

BB: Here is chance to make an impact. You are walking along Lake Michigan and find a Magic Lamp. What 3 things would you change in OOH today?

BW:  You mean your OOH Today? your newsletter?   Ha, no, I know what you meant. Here are 3 magical changes if I could.

  1. I would go back to real and personal client/vendor engagement. There used to be more dialogue, more interaction, more receptiveness to selling.  This led to highly knowledgeable buyers who knew the inventory and how it might or might not work.
  2. I would loosen sign code. Not necessarily making it a free–for-all in terms of added inventory, but making the approval thought process more consistent throughout the county or at least within each market.
  3. I would insist that buys are not just made solely off of results of data and or algorithms, but the majority of approvals would be based on common sense, knowledge of the product’s benefits, the strategy and how the product satisfies the strategy.

BB: What is missing in the Outdoor Advertising Community? What is your solution?

BW:  Billie, I have 3 solutions

First, Long-term OOH strategies. Planning needs to include a longer-term approach to OOH.  This doesn’t necessarily mean longer-term contracts, but it would allow us (operators) to be more in tuned with a client’s objectives and be more proactive with new ideas.

Second, Better Marketing. I believe this industry has always been weak in promoting our own features and benefits and explaining to decision makers why advertisers should chose this medium.

I believe this industry has always been weak in promoting our own features and benefits and explaining to decision makers why advertisers should chose this medium.

Last, More people (OOH Owners) should engage in outside sales representation…I happen to know of a really good rep firm.

Thank you Bob.

Check out- Bob Wolfe LinkedIn

This is a repost from September 27, 2017



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