Enterprise Legal Counsel

Automattic, the company behind WordPress.com, is seeking an experienced technology transactions attorney to serve as primary legal counsel to our VIP Team. The VIP Team provides support, hosting, training, and other services to some of the biggest and best WordPress sites on the web, for clients like Time Inc., Facebook, Microsoft, News Corp, FiveThirtyEight, The New York Times, and hundreds more.

We’re looking for an exceptional lawyer, who is an ace deal closer, gets things done with minimum friction, makes the complex seem simple, and eats enterprise SaaS contracts for breakfast.

In this role, you will:

  • Support our VIP Team on the wide range of legal issues that arise in our business, including enterprise-level technology transactions, licensing, intellectual property, and regulatory compliance, with a heavy focus on open source issues.
  • Help structure, draft, and negotiate commercial and technology agreements, as well as provide tactical advice on day-to-day legal matters, especially data security and privacy.
  • Design legal and business processes that enable the team to scale, like standardizing common deal terms and agreements.   


  • Have a JD from a US accredited law school, excellent academic credentials, admission to at least one US state bar and 3-5 years’ experience in legal practice (law firm and/or in-house).
  • Are well-versed in issues relevant to our business. Everything at Automattic is done on a global scale and in an international context; bonus points for breadth of experience outside of the US.
  • Possess an agile and curious mind. You’re not afraid to ask questions or admit when you are wrong.
  • Are business minded and very practical in addressing legal issues. We don’t write a lot of memos at Automattic. We solve problems and get things done.
  • Are keen to the legal and business challenges of supporting a world-class, enterprise grade technology platform that is 100% open source software.
  • Get up for the challenge of negotiating with some of the largest and most sophisticated enterprises in the world.
  • Thrive in a tech-centered, developer-focused environment, and are adept at collaborating with engineers and understanding technical, product details.
  • Have a healthy sense of humor, and an abiding spirit of idealism about your chosen profession.
  • Operate very independently.
  • Recognize that law is about the grey areas, and are comfortable living in them, while giving clear and actionable advice.
  • Excel at understanding complex topics and explaining them to others in clear, concise, terms.
  • Are a great writer.
  • Love the open internet and all it stands for.

About Automattic

We are the people behind WordPress.com, WooCommerce, Jetpack, Simplenote, Longreads, VaultPress, Akismet, Gravatar, Polldaddy, Cloudup, and more. We believe in making the web a better place.

We’re a distributed company with more than 650 Automatticians in 62 countries speaking 79 different languages. Our common goal is to democratize publishing so that anyone with a story can tell it, regardless of income, gender, politics, language, or where they live in the world.

We believe in Open Source and the vast majority of our work is available under the GPL.


Does this sound interesting? If yes, please send a short email to jobs @ automattic.com telling us about yourself and attach a résumé.

Let us know what you can contribute to the team. Include the title of the position you’re applying for and your name in the subject. Proofread! Make sure you spell and capitalize WordPress and Automattic correctly. We are lucky to receive hundreds of applications for every position, so try to make your application stand out. If you apply for multiple positions or send multiple emails there will be one reply.

Want to increase your chances of standing out? If so, please tell us: what is your approach to negotiation, and what do you think makes a good business deal? If you’re legal counsel to a Fortune 100 company, what excites and what scares you the most about using open source software in your enterprise?

Also, please make sure to include at least one lawyer joke in the materials you submit.

Interested in seeing what other positions we have available? We have the updated list here: https://vip.wordpress.com/careers/

Ready to get started?

Drop us a note.

No matter where you are in the planning process, we’re happy to help, and we’re actual humans here on the other side of the form. 👋 We’re here to discuss your challenges and plans, evaluate your existing resources or a potential partner, or even make some initial recommendations. And, of course, we’re here to help any time you’re in the market for some robust WordPress awesomeness.