Fast Talk: Freewheel CTO Diane Yu On Making Video Into Ad Revenue, Lemons Into Lemonade

When video ad tech firm Freewheel let a big fish slip from its line, CTO Diane Yu had to rally her teams to find new uses for all the technical assets they developed for the prospective client. Breaking bad news is never easy, but here’s what worked at Freewheel.

Fast Talk: Freewheel CTO Diane Yu On Making Video Into Ad Revenue, Lemons Into Lemonade


Diane Yu sees a $160 billion worldwide TV market opportunity for her company and its clients. As chief technology officer and cofounder of Freewheel–an ad tech firm with 130 full-time employees and U.S. headquarters in New York–Yu helps major television networks make sense of all the ads they’re selling, and helps brands figure out what works to reach audiences wherever they’re watching video content, now.

When she delivers great news, she wants to make it really great, of course. Through its proprietary software, Freewheel just managed its 100 billionth ad impression, which she reported to her employees joyfully.

Freewheel also recently helped a network (they can’t disclose which one) double the number of ads it could sell per “commercial pod” within a given video. Reporting to the network that this technical tweak had, in fact, resulted in a doubling of their advertising revenue per video was fun work for Yu.

Some of Freewheel’s clients include ESPN, Turner, Discovery and VEVO. The company has helped broadcasters manage and maximize the delivery of ads for live, news breaking events and programming that ranges from FIFA World Cup and the Royal Wedding, which are planned, to the rescue of the Chilean miners, obviously not planned.

But working in a rapidly changing industry means Yu finds herself breaking bad news regularly, too. When Freewheel let a big fish slip from the line in a huge sales pitch this past year, Yu had to rally her team to stay optimistic, and find new uses for the technical assets they had developed for that prospective client.


In an era when video production and distribution is about as easy as snapping a photo, and mobile devices with high quality screens are proliferating, reaching viewers and making money on video programming isn’t going to get any easier.

Yu recently shared tips with Fast Company on keeping a high tech team going strong through the peaks and valleys of a rapidly changing business.

FAST COMPANY: What service do you provide? What do you make, and who do you sell it to? 

DIANE YU: We are a technology company that provides enterprise-level media and entertainment companies with the infrastructure and tools needed to run professional content businesses in the new media landscape. In short, we help them monetize and manage advertising and operations for their video content across a multiplicity of devices including laptops, iPads, smart phones, and more.

How did you come up with the idea for the company?


In 2007, Jon Heller, Doug Knopper and I–we knew each other from our days at DoubleClick–founded Freewheel. I was still running engineering teams at DoubleClick when it was acquired by Google, whereas Doug and Jon left before me, for different reasons.

At the time, we saw a big market opportunity in monetizing distributed professional video content. Consumers want to watch high quality content whenever and wherever they want it. Enabling this to happen and making sure all companies involved in making this happen are properly credited for what they do is a big business, and it was a completely empty field back then.

With Jon on product, Doug on sales and marketing, and myself as the engineering lead building the product, we thought our combined experience and capabilities between the three of us made us a kind of dream team to realize this idea. Strong execution has been the number one reason why we have been…winning big customers one after another.

What’s changing about your business, today? What’s the biggest new problem your customers are facing? Why does that matter to the average regular media consumer? 

A lot is changing. The idea that a consumer could access their favorite, full-length shows online or on their phone for free with ads or for a small fee was essentially a new concept in 2007. Hulu was announced in March 2007, for example. During a conference this past June, executives from Disney, Turner and Comcast announced that in two years, 75% of TV content will be available online and across mobile devices. Also, the iPad didn’t even exist when we launched.


Based on our most recent monetization report (Q2 2011), we’re seeing that online video is continuing on the path to generating revenue much like television: ad loads correlate to content length and reflect classic advertising seasonality.

Consumers continue to embrace ad-supported content models, even as ad loads increase over time. Long-form content contains an average of three video ads per video view with an average ad completion rate of 81%–this means there will be more money going into supporting our favorite shows online through advertising, which equals more viewing opportunities for consumers.

Wireless video viewing doubled from the first quarter to the second quarter of 2011, driven by the iPad. Now, iPads encompass the largest volume of wireless viewing, up 11% since early 2011.

[Cable] companies like Comcast are protecting their cable rates by enabling their subscribers to go through an authentication process and view their cable-subscribed content on multiple devices. Microsoft recently announced deals with various cable networks to stream television via the Xbox, and countless others are joining in.

Have you ever had to break bad news to an employee, team of employees, client, partner or investor? When? What was the worst? 


Yes, we lost a key prospect–a large media company. We ended up losing them because they chose to go in a different direction in terms of technology strategy with closed systems. As we had so much momentum at the time, it was a very difficult loss. What we did is look at the ‘feature wish list’ of this prospect, and had ended up building all of them [during the pitch process]. This was a good lesson in ‘everything working out for a reason’ as the capabilities we built aided us in winning future, high profile customers like Discovery and FOX.

What are some of the worst kinds of bad news you have to deliver, regularly? 

Telling the customer, “no,” or “not now,” is always very difficult. The reason we have to say no to customers is because we want to deliver a technology product that is the correct solution for our customer’s problem and is of the utmost quality.

Sometimes the customer will say, “why can’t you do this?” or “I’m going to switch companies!” However, we stand by our professional opinion and ultimately what would best benefit the customer. We don’t tell them ‘no’ and then let them sit in pain, obviously. We take the time to understand their pain points, remain flexible and find some solution to put in place for the time being, whenever we can.

We are finding that our customers come back and trust us even more once we deliver that. They realize that we said “no” or “not yet” for valid reasons when we take that approach. Happy customers equate to renewals, which is obviously good for our bottom line.


How do you manage to keep everyone productive after you’ve just delivered bad news? 

It’s about quickly re-directing focus. In the example of losing one of our largest prospects, we quickly got teams [that were involved in the pitch] working on existing implementations, making sure that those were moving along smoothly and that our current customers remained happy. We made sure that everyone understood there are certain times that we don’t get what we want. The extra time given to us to remain focused on what we already had was beneficial in dealing with a few large customers we already had, in the end.

Why aren’t more females involved in tech entrepreneurship? 

I wouldn’t focus on why there aren’t enough women involved… Men and women think differently and they naturally are interested in different things. I would rather focus on what we can do: creating a more sustainable technology environment where those women do get involved and can thrive. It is our job to create an environment where men and women are evaluated and compensated equally for their career progression based on performance. It is our job to build a culture where different perspectives and approaches are recognized and appreciated.

What’s the worst news you ever got at work, yourself? How did you recover, and succeed after that?


When the first Internet bubble burst in early 2000, I had to lay off my entire team via several layoffs at DoubleClick, as a new manager who just started her management career. That was very difficult and painful. As painful as it was, it also helped me to grow tremendously in a short time period. I learned why a company should never expand without a purpose and what the consequences were. I also learned how important it is to fairly evaluate people for survival. Always keeping a positive attitude, learning from mistakes and [how not to fall into] that same situation helped me grow continuously in my career.

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About the author

Lora Kolodny is a tech editor and writer with She formerly worked as the green tech editor at TechCrunch, was a NYTimes small business blogger, and staff reporter at Inc