Woe The Digital Sale: Switching Sides

I just got promoted to media supervisor at my agency job.  I am starting to wonder about my career path and becoming a media director eventually -- but I'm also intrigued by the secret lives of salespeople.  I wonder if I should start exploring sales side opportunities before I get too senior on this side of the business.  Would my agency experience prepare me for this kind of position?  And is it ever too late to switch sides?

Amy says:  I have always wondered about the secret lives of salespeople: the freedom, the glamour, and especially the expense account!  Being naturally curious, aka very nosy, I would often ask my favorite reps about their job satisfaction, the pressures of selling and the ways that Web sites work internally -- both process and politics. 

A lot of what we do as buyers is definitely mirrored by sellers, it seems.  We have clients, they have clients.  We have tagging issues, they have tagging issues.  And both of us are constantly pitching our wares to advertisers.



From a content perspective, you are probably more than qualified to join a sales organization.  You know what advertisers need from online advertising and can provide an insider's view on what makes a buyer sign on the dotted line.  Also, you have an understanding of any site's competitor set, so you can bring value there.  What I think you would probably like is being able to learn about different agencies and how they do business compared with what you are used to.

What you may not be used to is cataloging all of your activities and worrying about making your quota.  Sales management is always going to be asking what have you done for me lately. I know many folks who are required to have dozens of meetings per week and record all activities associated with them.  CRM software helps out with this -- but it is way more detailed than filling out a status report for a weekly client meeting. 

The other main difference, of course, is compensation.  If you are a salesperson, your base salary may cover your living expenses -- but you will probably rely on your bonus to buy that Louis Vuitton bag or new Burton snowboard.  Bonuses only come along when you meet your quota, or your team does, and in this economy it may be tough.  Choosing the right sales team is important too, since you want to be working with people who have a shared interest in success.

If you are thinking about making the switch, start asking questions of your favorite vendors.  Determine your monthly budget so you know what you need in terms of salary and bonus.  I don't think it is ever too late to join a sales-side company; many senior agency execs join "the dark side" in marketing and strategy positions.  But maybe the sales side isn't so "dark" after all, and it will be a career that suits you better in the end. 

Jason, what do you think?  Could an agency guy hack it in the fast-paced world of selling?

Jason says: I envision a very secretive recruitment process, hopeful media executives pitching you on the benefits of joining their team, a flood of speculation from the twitterati as to your prospective whereabouts, and then the culmination in your press conference, where you proclaim "I'm taking my media talents to South Beach.... the Web site."

OK, maybe not. Basically, I believe great salespeople are born, not made. As such, we are always on the lookout for exceptional talent (excepting the digital near-apocalypse of early 2001 and the ad depression of 2009). The reason we often look for talent over experience is simply because, in a business so young, it is more difficult to accumulate meaningful experience. I have always said that I believe in hiring great businesspeople with the relevant industry expertise.

And you cannot get more relevant experience selling digital media than working in an ad agency buying digital media. I have found that salespeople who come from ad agencies can do extraordinarily well in the world of digital ad sales. Along with whatever business category experience they may have (e.g., health, technology, retail), they also know how the agency world works, which is right up there with knowing how to assemble a carburetor or figuring out how to get the wrapping off a CD.

These turncoats might actually know how to navigate the ridiculous world of "RFP du jour" that some digital agencies have created. For instance, having someone from the agency side could help our team understand why we received an RFP at 4 p.m. on Friday that was due Monday at 10 a.m., for a company that posts over $600 million in annual sales, while the RFP is for a whopping $7,000. Similarly, perhaps they can help us work a system where the largest CPG brands in the world plan digital media for every brand, individually, from scratch, for each effort, rather than as a whole a few times a year (as they do in TV, print, outdoor and radio).

Ax-grinding aside, if you are ready to come sell some ads, also be ready to a) rarely get a phone call/email returned b) barely receive feedback when you don't make the plan, and c) be asked to make a contribution to an agency's charitable endeavor even when that agency has not given you a dime of revenue in years. Oops, ax-grinding still alive and well. Now, I'm thinking about crossing over.

Well, if that doesn't bother you and you've got the necessary attitude, temperament, and moxie, my fellow Jewish poet and I welcome you:  "Give me your tired, your poor, your huddled masses yearning to breathe free, The wretched refuse of your teeming shore. Send these, the homeless, tempest-tossed to me, I lift my lamp beside the golden door!

Come on over, my agency brethren, I've got a Vuitton bag waiting as a signing bonus! And you soon will find out if you were born for this.

7 comments about "Woe The Digital Sale: Switching Sides ".
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  1. Brian Quinn, July 29, 2010 at 10:57 a.m.

    Nice job Amy and Jason. i have seen many former agency folks thrive on the sales side. But, for publishers you must be very honest with yourself in evaluating talent. Knowledge of the inside agency workings, experience being on the receiving end of sales pitches and expertise in a category are not nearly as important as that "born salesperson" that Jason describes. Can this person run a meeting correctly, e.g. making it a conversation and not a power point exercise. Can they manage a territory and quickly figure out what the priorities are? Bottomline: we need the best talent possible in digital media. Cheers... BQ

  2. Paula Lynn from Who Else Unlimited, July 29, 2010 at 11:06 a.m.

    Agency people can make the best salespeople for all of the reasons stated above. However, also be prepared that most expenses may not be paid for you but they are deductable. You may never obtain a salary past the first few months and work only on commission....Make sure you have employee status ----, but you still can rake in more money as long as you can handle shifts in seasonal earnings. Also find out how accounts are doled out, what their policy is in obtaining accounts, what the company's revolving sales door is like and you are fine with sharks and baracudas. Just keep your options open. Your expertise can help keep you on top.

  3. Wendy Hidenrick from AwesomenessTV, July 29, 2010 at 11:46 a.m.

    Jason - I have to say, that axe grinding happens... I am not faulting you for that at all!!!

    BUT when I receive a note from my agency contact at 6pm on a Friday, and I have already been at Happy Hour for nearly and hour (or two on occasion) I wonder why more agency people don't come over to the dark side. But the fact is you have to have a THICK skin to be in sales. If your sensitivo - then forget it. I have been treated poorly in the past and not just once. You have to be able to stay positive and hope for a better outcome.

    Net-net: If you have a positive disposition and drive, then you can probably hack it.

  4. Matt Johnson from Evolution Marketing, July 29, 2010 at 12:23 p.m.

    I made the jump just about 3 years ago now. I grew up in the media departments among the Minneapolis agency world and after 10-years I said love ya but gotta go somewhere else. All the points made are true and right now my most difficult part is managing the priorities in my territory. I wish I would have had this advice when I made the leap as I learned it on the fly at the first company but am much the wiser now and things are really starting to look up. One thing though - just because you were on the agency side and understand how they work, doesn't mean you'll understand why you're asked for the proposal within 24-hrs and for only $7k. But you do learn a lot about how other agencies truly function. Make the jump, you can always go back - if you really want to. May the force be with you!

  5. R.J. Lewis from e-Healthcare Solutions, LLC, July 29, 2010 at 2:47 p.m.

    This is a great career article and the timing is perfect. We have two online advertising sales positions open, and when we recruit we LOOK for online digital ad agency planners and buyers. Agencies provide and excellent training environment for future online sellers. Since they often don't pay the media folks very well (but instead sweeten the deal with the promise all of the glamor, glitz and swag they'll get from vendors), it is often a very good move financially for an agency person to move onto the sell side. All of the points in your article (and these comments) are spot on. It does take a strong confident person because you are moving from a world where people jump when you call them to one where they just don't answer the phone unless you get creative. Have a thick skin, and expect some pressure - selling is one of the most measurable jobs on the planet. You are either winning business or not. But for those who are personable, passionate and willing to work hard, the rewards are literally unlimited. Great sales people can make more than CEO's and CEO's willingly pay great performers for results.

    For all of you media folks excited about making the leap, we have two openings!

  6. Shira Dinour from Innovid, July 29, 2010 at 7:39 p.m.

    Great article. I made the move to the "dark side" in January after 10 years in media planning. I did exactly what Amy said which was talk with all of my sales people (those who I trusted most) and asked them a ton of questions. And, most importantly, I waited for the right opportunity. I had the fortune of still being employed during my job search so I wasn't in any rush and made sure that I would have the proper training and support to help me succeed in my new sales job. I LOVE my new career choice and highly recommend it.

  7. Tony Anderson from Incline Video, July 30, 2010 at 12:07 p.m.

    I've been working in the online media space for 10+ years having served at the Director of Ad Sales Level on the Publisher/Ad Network side. Also, I've done Media Planning Buying for a few of the Larger Ad Agencies in SF. In addition I've also ran Ad Operations on all sides.

    I believe we're all multi-talented and there is too much focus on "Specializations" within our industry. We each have a choice to be type cast in a certain role or add to our experience and ultimately our market value by working on both the agency and publisher side. Both are equally rewarding! These days I just love start-ups!

    Tony Anderson -

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