Meet Jesse from Jetpack: Director of Innovation, Entrepreneur, Writer, and Botnet Fighter

Ever wonder what it’s like being the Director of Innovation at one of the world’s most visionary companies? Wonder no more. We sat down with Jesse Friedman, Director of Innovation for Jetpack at Automattic. We picked his brain on all things Jetpack, WordPress, Automattic, open source, botnets, and woodworking. 

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Q. The word “innovation” is in your title. It’s used so often it can become meaningless — how do you understand innovation? 

I love the definition of innovation from Scott Berkun, who wrote “The Year Without Pants” about his experience working at Automattic. He says innovation is enacting significant positive change. I love that. Because the moment this happens, you’re disrupting and changing the product, the operational flows, and the business. 

When you start to look at ways to improve something, it’s important that you feel free to experiment and are comfortable saying that even though you’re being smart and safe, the thing you’re trying might fail. That allows you the freedom to experiment. Innovation can be a lot simpler than people make it out to be. 

Q. That’s great.  How are you enacting positive change over at Jetpack?

Right now, I’m doing a lot of work to enhance personalization — how do I change the product from being something that’s all things to all people (and therefore being not quite perfect for anyone) to being something that does exactly the right things for you?

We’re working on a recommendation engine to do that. We’re making Jetpack more configurable so customers can have more tailored experiences. So when a person arrives on a page, it already knows something about them. Then they answer a few questions so Jetpack can make recommendations specifically for them. 

Q. Can you walk us through what that looks like? 

Jetpack may ask things like: 

• Are you planning to make money with your site? If yes, are you interested in affiliate advertising? 
• Are you expanding a brick-and-mortar business online, or do you do in-person sales only? 
• Will you be shipping goods?

Based on those answers, it can make decisions or recommendations for you. For example, it might recommend WooCommerce or some specific Woo extensions. The idea is that you get the help you need in real time. 

Q. Can you tell us about a typical day in your life as Jetpack’s Director of Innovation?

The title is my way of formalizing a chaotic role in which I get my hands dirty in a little bit of everything. I’m a mixed bag. I write code. I do growth/business development and marketing. I negotiate contracts. I also work on strategic partnerships. 

Half the time I address the needs of partners: consult, strategize, run reports, and gain insights into what they’re doing to make our products fit their needs. The other half of the time, I’m working on the Jetpack product, building features and helping with the marketing message. 

Q. What kinds of companies typically partner with Jetpack? 

Mostly hosting companies. My major focus is on strategic partnerships and helping our partners to provide a better Jetpack experience for their customers. Jetpack is a tool with a variety of features, and our mission is to bring the best and most relevant parts of Jetpack to those specific partners.  

Q. What’s important to hosting companies? 

Streamlining experiences. One hosting company wanted to streamline its onboarding process to help users build their sites faster and reduce the time to go live. Jetpack is a built-in tool in their arsenal, rather than something they have to install, activate, and set up. 

Things like themes, design tools, imagery, site speed, and security are important. With a partnership, we’re able to prioritize these features early on so people who use Jetpack begin to understand that security and performance are not something that’s optional, but something that’s actually built into their platform. 

Q. Automattic is known for its globally distributed workforce. What does your day to day look like working from home? 

My day is generally dictated by the number of meetings I have. I work with a lot of third-party companies, not all of whom necessarily dig the asynchronous, distributed life, so in-person meetings and emails are super important. I try to work around the needs of my colleagues and partners. I’m an early bird, so 6:00 a.m. meetings are not uncommon with people in Europe and Asia. 

Q. How did you end up at Automattic and Jetpack?

I built my first HTML website when I was 16. I received a degree in Web Management & Internet Commerce from Johnson & Wales University in Rhode Island and ended up becoming an adjunct professor there for seven years. I taught hundreds of students how to build WordPress websites on the side while I was progressing through a few roles in advertising, insurance, and WordPress security. Then, I started consulting with major companies like Lego on personalization. 

Throughout it all, I was building with WordPress. Around 2010, I started speaking at conferences like the Future of Web Design and ended up writing a few books about WordPress. I spoke at SXSW and ended up meeting Matt (Mullenweg CEO, Automattic). It was a cool experience because he and I had the only two WordPress talks at SXSW that year. The following year, we met again, and I introduced him to a product my colleagues at the time and I were working on called BruteProtect.

Q. What did that product do? 

It stopped botnets. It was a cloud-powered brute force protection plugin for WordPress that protected sites from malicious logins. It used the knowledge it gained from malicious login attempts across all sites to protect everyone using it. 

If Hosting Company A is tracking all attack vectors — hackers’ methods of accessing a website — that doesn’t help anyone using Hosting Company B. BruteProtect (which is now a part of Jetpack, called Jetpack Protect) combines all that information across the WordPress landscape and uses that intelligence to protect everyone. Automattic acquired the company, and that’s how I became part of the team. The brute force attack protection is now built into Jetpack, and it’s blocked trillions of malicious login attempts. 

Q. How do you describe Jetpack to people? 

The beauty of Jetpack, to me, is that it has a robust library of features, but is so simple and well thought-out that it grows with you.

When you look at the core features, it has what every single site needs as a foundation, whether it’s an eCommerce site, a wedding site, or a blog. Jetpack creates a solid foundational layer of security and performance, which I recommend to every single person who uses WordPress. 

As the site grows and needs more functionality, you have all those features within Jetpack at your disposal and can turn them on as you need them. That’s huge. These are what I call “light switch features.” You switch on the feature and it just works, no configuration needed. But you can go on to customize them if you want.  

Q. Why is this so important? 

You save yourself countless hours of research by just expanding the features you need with a tool that you’re already using. Otherwise, you’d have to figure out if you need a plugin, research what’s out there, evaluate each option, read the reviews, understand whether they have a good support team, and so on. 

“Immediately after enabling Jetpack Related Posts, the Albuquerque Journal — a newspaper with 580k paid print subscribers and three million monthly page views — increased engagement by four percent.”

Jesse Friedman, Director of Innovation, Jetpack

Q. What’s one of the features that you really love?

One of my favorites is Related Posts, a tool that helps keep visitors on your site longer by showing them related content they might be interested in. It’s so elegant and wonderfully designed, and dramatically increases marketing performance. Immediately after enabling Jetpack Related Posts, the Albuquerque Journal — a newspaper with 580k paid print subscribers and three million monthly page views — increased engagement by four percent. 

Q.  Jetpack does a lot!

Jetpack powers WordPress.com. It was designed years ago to bring better services to WordPress. There are 40-plus features built into Jetpack and everyone has a few favorites. While the foundational needs are the same for everyone, everyone has a different story and a different set of tools they need to use to tell that story. 

Last year, we disabled several Jetpack features out of the gate. We looked at data on the features being used by the majority of customers and followed our own mantra: get out of the way. Now when you turn on and connect, Jetpack has a significant reduction in automatically-enabled features. But all those features are easily accessible and can be turned on with the flip of a switch. That was us listening to the community. We’re not running unnecessary code on sites where people aren’t using those features.

Q. Can you talk about the company’s commitment to Open Source? 

WordPress is open source. Not because it has to be, but because it’s part of our core values — because we know this is the greatest idea of our generation.

TV host and philosopher Jason Silva, says in his Ted Talk, Radical Openness, that ideas can breed. I share an idea with you and you make it better by building on it. Open source code is viewable, portable, modifiable, and forkable. The Jetpack plugin is also open source, and we encourage improvements and contributions from the community. There’s nothing in our plugin that’s proprietary that you can’t view or dissect yourself. Anyone can contribute to it. We have a ton of people expanding and improving Jetpack. 

It speaks to the idea that nothing is off the table and we can go in any direction, pivot, and change. That means WordPress never stops changing. It’s always adapting. It’s owned by the community of people using it rather than a single corporation. Bloggers trying to create social change have just as much voice as companies paying hundreds of thousands of dollars to get their product out there. 

Q. How does that all fit in with the commitment to democratize publishing?  

One of the core values of Automattic is to democratize publishing. That can mean different things to different people. An aspiring journalist in a part of the world that may not have fast internet connections can still download the WordPress app and get the word out on what’s happening to enable positive change.

It can also help a local business in the way it operates. It can help people become entrepreneurs and provide them with a revenue source. It can be used by school-age kids who want to start a nonprofit, create a fundraiser, or do what they want to do online. It’s endless.

Q. We’ve interviewed a lot of people at Automattic. Why are they all so cool? 

That question makes me think of the quote by Emerson, “An institution is the lengthened shadow of one man.” Matt is probably the most emphatic, innovative, future-thinking CEO I’ve ever worked for. His product is Automattic. It’s the culture and the people and the benefits you get from working here. There’s a deep investment in the people and culture at a level that I’ve never seen at any other company. Every single person here feels that.

Everyone here has a unique story. The application process isn’t easy. It’s more than a litmus test. It’s designed to get an understanding of whether the person is fundamentally right for the company and vice versa, which is a big reason why there’s such a low turnover rate.

Q. What is it like working with so many people you only see once a year? 

Here, the culture is one you become so deeply embedded in that your colleagues become your friends and your Slack channels become your social network. Slack is the area between cubes and conference rooms and the water cooler. I barely use Twitter or Instagram anymore. If I have something worth sharing, I’ll share it with family via text and I’ll share it with friends in Slack. You become quite close to the people you work with.

Q. What are your passions outside of technology? 

I’m into woodworking. I love building functional things. One of my largest projects was a pirate ship jungle gym for my son that’s in our backyard. He’s made me walk the plank many times. 

I spend most of my time with my family, and I love to travel with them. I normally travel a lot (although this has obviously changed in 2020) to meet partners and attend conferences all over the world. Often, I return to these destinations with my family, or they join me when work is done. 

My son is 12. He’s been to Denmark, England, Holland, Brussels, France, Germany, Switzerland, and Ireland. He’s seen Stonehenge and the Mona Lisa and the Alps and stood on the Eiffel Tower. That’s the best gift I’ve gotten from working at Automattic.

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