An interview with Cindy Jeffers, CEO and CTO of Salon Media Group

Part 2 in a series of CTO interviews 


There are many different models for the role of the Chief Technology Officer. In the fast moving world of digital media, no matter how the CTO does the job, the role requires its holder “to constantly balance technical and people skills, and to look ahead while fulfilling the here and now,” as a recent article in Information Week put it better than I might. Recently I had the opportunity to sit down with CTOs from very different digital media companies to understand how they think about the role, what they have in common and where they differ in approach. Over the next few weeks I’ll publish a summary of each of these discussions. (The first- with Jesse Knight, CTO of Vice, is here.)

Second in the series is Cindy Jeffers, who happens to be both CEO and CTO for Salon Media Group, positions she has held since 2012. Jeffers is credited with leading a turnaround for the business after a few trying years, and she’s focused on instituting a lean, iterative approach to tech that she says she first learned in NYU’s ITP program. I sat down with Jeffers in her midtown offices.


1) We hear all the time that the pace of technological change has sped up. How has that changed the job of the CTO, particularly in digital media?

Since I’ve always been working in technology it has always felt fast. There is always change. It’s very important that we are constantly experimenting, constantly iterating- taking a nugget of an idea and seeing what will be most interesting to our users, testing that and building out the product from there. We try to work in a way that is less native to media and more native to technology.

Across the company we’ve become a lot more experimental, such as the way editors are analyzing traffic and referrals. We’ve seen a huge shift into mobile over the past year; it’s surpassed desktop. We’re ahead of the curve of that transition and we really build all the sites with mobile as the most important platform. On the sales side we’ve focused on rethinking solutions. We’ve started doing native, going way beyond the traditional experiences advertisers have with media companies to deliver more innovative experiences.

Tech companies think about innovation all the time, but I don’t think media companies necessarily do. There are a few companies that do think like tech companies and as a result you are seeing changes in the way their audiences grow and their revenues grow. We are in line with that- it’s not just that innovation is cool, it’s that it makes sense for the business.

2) You must get a thousand pitches from vendors a year, each promising you a new software or widget that will change your business. How do you filter, how do you sort, and what types of things stand out? How much do you buy vs build?

Buy vs. build depends on the size of the company and the amount of tech resources you have. We are a small company so we really focus on the right balance between what we really want. The advantage of ‘build’ is complete control of the pipeline. Ideally we would build everything ourselves. But sometimes it makes sense to use a vendor. For instance, last summer we switched to Livefyre- a commenting platform that takes a big piece of the code base outside of our control but also outside of our tech pipeline. For the most part it is the best commenting platform we’ve seen. You have to weigh the roadmap- what are the most important pieces. Any proprietary thinking we do in terms of how we curate content, we do that in house.

3) What types of time horizons are you working with when thinking of how to incorporate new technologies into the business? What technologies do you think stand the most chance to change your business in the next 3-5 years?

Things change quickly. It’s really important to build small pieces of a larger idea, to see if it’s still a priority as things move along. Sometimes things become more of a priority, and sometimes they don’t; you have to manage your tech pipeline and respond accordingly. Ten year tech planning is not realistic. There are things we know will be important for the next few years- for instance, mobile phones and social media will continue to have a big impact. Look at wearables. There is not a huge audience right now for Google Glass, Fitbit or the Samsung watch. But as wearables proliferate, people will become more comfortable with them. There will be a larger audience, and we’ll have to think through what the experience is for those devices. There has to be an audience and a platform before we can act.

Building iteratively is so important; we’re data driven and we build as a result of learnings through data, so there are reasons to build a new product feature. If someone has an idea that is more gut driven, we’ll build a small piece of it and build it out from there if it is working.

4) How do you personally keep up to date on the latest?

Getting out there and going to conferences, being part of things like the hackathon at TechCrunch Disrupt, getting in the mix of what people are building, that’s really important. I think of myself as an early adopter- I’m just endlessly curious about how humans interact with technology. The tech side is one hat, the CEO hat is the biggest hat; there are many responsibilities in that realm that don’t involve gadgets. But technology is a vital piece of what we do.

The biggest thread throughout my career has been understanding how humans work with technology, and the curiosity to understand that better everyday. Maybe the most important thing I learned at ITP was how to learn- since then I have the tools to continue to explore over time.

5) When you think about the broader organization, how do you help the average employee improve their technological acumen, and raise the overall mean?

Everyone is aware of technology. Our editorial team I find to be very technically savvy. They are obsessed with analytics, with changes in Facebook or Google algorithms; it’s a really tech hungry group. We did start online, so people are really aware of what’s going on.

We really want to be an innovative leader in media and tech. There has been a convergence in the last 15 years between the two. Everyone in media has to be an innovator, think of themselves as experimenters, and be okay with failure. You have to try a lot of things and if you succeed in a few of them, you are doing really well. A lot of people get hung up on failure. You just have to do it, and see if it works. Of course, not so much that you are risking things- but if it’s not a big deal, just build it. All failure should come with a lot of data that you can learn from. It is a big deal if you fail and don’t learn anything.


Justin Hendrix is Executive Director of NYC Media Lab. Reach him at justin [dot] hendrix [at] nycmedialab [dot] org or follow him on Twitter @justinhendrix.