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AdTech Reboot

Trust Web Times Interview Series: Darryl Winter ; Winter Media Group

Marc Goldberg

Marc Goldberg

Author at The Trust Web Times
Marc Goldberg

Marc Goldberg

Author at The Trust Web Times

Marc Goldberg
 is a contributor for the Trust Web Times. Marc is also the Principal at Stages Collective. Stages Collective helps companies at different life stages in a variety of ways. Business Development, go-to market strategies, Landscape analysis and as an additional recruiting resource.

Darryl Winter  is the President and Founder of Winter Media Group.

We exchanged emails for this interview and it has been slightly condensed and edited.

Tell us about your journey?

I started my career in media in 1997 (gosh I feel old typing that) as a TV sales assistant on TBS/TNT Entertainment.  We had an amazing team and I loved the television business but in 99 there was a planner opening on the business development team at CNN Interactive.  I jumped at the opportunity.  It was early days for the digital media ecosystem and I wanted to take a ride on the rocketship.  It didn’t disappoint.  Back then everything was possible and business development teams were just as large as digital sales teams.  We worked to distribute CNN content everywhere….mobile, desktop and PDA’s.  Remember your trusty palm pilot?!?  

I do. DOPE WARS was my game!

Ha. It was incredibly creative, exciting and opportunities for monetization of CNN content seemed endless.  I even remember when I first saw video on a mobile phone probably 5 years earlier then that technology was available to the broader consumer market.  I still recount that time as one of the most impactful times in my career and it shaped my thinking about the digital business to this very day.  

Two years later AOL and Time Warner merged.  AOL assumed control of TW’s inventory and I was soon out of a job.  Business development gigs were extremely hard to come by after the market crashed so I threw myself into the ring, literally, and went to WWE as a national account executive.  Another great 2 years.  If you were looking to hit a young male target there were few better places to go to for scale.  It was a great learning experience and gave me the opportunity to sell but I wanted to go back to a company that I had a personal connection with content wise and with that I was fortunate to have gotten a position as an AE at Discovery.  Discovery’s were initially largely display and I thought there would be enormous upside once they started streaming video en masse.   Like all major media companies in the early to mid 2000’s they bought properties, sold properties and built new ones to cater to changing user appetites.  Amazing company, phenomenal leadership, it was a dream come true.  I worked my way up to management, went through a few reorgs and after 11 years decided it was time to leave.  After that I did a two year stint at and then got the band back together with my former CNN boss, Nick Johnson, at McClatchy where he brought me in to run National Digital sales.  Another two year run.  Nick and I both left McClatchy at the same time and we started doing strategy and sales for a few companies.  I loved the variety of working on different businesses and felt more creative then I had in years.  Nick went on to be the CRO of Spotter and I continued by starting Winter Media Group.  I wouldn’t be where I am today without Nick and forever grateful to him for his friendship and guidance over the last 20+ years. 

So what does the winter media group do?

Simply put, Winter Media Group is a fractional sales organization designed to help companies in various maturity stages set the right foundation for revenue growth.  We provide strategy, go to market narrative + collateral development, audience development, financial planning and a network of sellers focused on agency / publisher demand.   

I thought everything was automated and bought programmatically. With cookies eventually going away do you see sponsorship model and ownership packages growing?

I love this question.  I think about it every day.  It’s getting harder and harder to be a lower to middle tier publisher.  The top 20+ properties get $.70/$1 and programmatic dominance will only increase as it gains hold in television as the preferred way of doing business.  That said a good idea is a good idea and differentiated publishers with the vision and patience for longer sales cycle sponsorship or custom programs will win.  Not just because they’re getting a better price point by selling more of their inventory directly but because they’re providing that sought after deep connection between their valuable brand and their client.  Context does matter.      

What are the challenges premium publishers are having that you see that are fixable?

I think one of the problems they have is top down budget exercises.  If we have this many sales people and make this many calls we should be able to achieve this kind of revenue per seller.  It never works out.  Do you have an audience that’s valuable?  Do you have content that’s differentiated?  Have you made proper assumptions for ramp time and market penetration?  Another issue can be sponsorship price points.  I feel like often pubs can go out with asks that immediately price them out of the market.  Especially in that middle tier.  After you account for the top 20+ and programmatic, buyers probably have enough money for direct buys with a handful of sites.  The value the buyer is getting in relation to the asking price should be screaming off the page.   

What challenges do you see on the buy side?

Time. Period.  There’s only so many hours in the day.  I’ve heard countless stories of buyers working 12 hour days, weekends, etc.  Many are exhausted with no end in sight.  Be respectful of their time, don’t take it personally if they’re not on camera because they’ve been in Zoom meetings all day.  Have a purpose, craft your follow up, don’t mail it in.

You just traveled to Iceland. I am a lil’ jelly. Do you see business travel coming back? Are you having more in person meetings?

Amazing trip to Iceland thanks.  Easy flight, great adventure trip with the family, lots of fond memories including everyone getting Covid.  It seems like business travel for internal purposes is definitely back.  I don’t hear about a lot of in person agency meetings or events but I’m certainly trying to meet face to face with my clients whenever possible.

If you could take a client out tomorrow night. Where would you go?

I’ve started taking clients out to lunch or dinner in their hometowns if it’s in the tri state area.  People are still working a good deal from home so a bite close to home is usually preferred.  That said I just started working for a company where the founder has another business… air balloon charters.  Now that’s a solid client outing!

I am scared of heights, please don’t call me for that one.