Coffee With: Pinterest Engineering Site Lead Ruben Ortega

Ruben Ortega
Location: Seattle, WA
Job: Engineering Site Lead, Pinterest, Ruben Ortega
Education: B.S. in Information and Computer Science, University of California, Irvine; M.S. in, Computer Science and Engineering, University of Washington
Pinterest: @Ruben Ortega

What was your very first job? And how about your very first job in tech?

My first non-family paycheck came from working the graveyard shift at a distribution center. I worked in the freezer section, shipping food to a local grocery-store chain. When I graduated from the University of Washington with an M.S. in computer science and engineering, I landed my first technology job as a developer at Siemens Medical Ultrasound, where I helped build the software for one of the first digital and color ultrasound imaging systems.

What were the best and worst parts of that first job?

I found a lot of joy in being able to use my degree to build software that actually helped save lives. I did, however, find it frustrating that it typically took around five to seven years to launch a single version of software, given all the regulations and restrictions in the healthcare space.

Read: Day In The Life: Pinterest Diversity Programs Specialist Meet Abby Maldonado

How has your engineering career evolved since then?

I left Siemens to work at a couple of small internet companies before landing at Amazon in 1998. When I joined, I thought I would only be there for six months, but I ended up staying for over nine years. I loved the speed of building and shipping software on demand. I worked on Amazon’s search engine, inventing a key algorithm that took the words people used in the search box, weighted them by their purchases, decayed the data over time, and then re-weighted the search results based on this activity. Launching this feature was a eureka moment. The search results were visibly better compared to the original (and the customers thought so too). The usability of the search engine dramatically increased as customers had to type fewer words to find what they were looking for. Over time, this implementation and idea was attributable to billions of dollars in sales.

How did you transition from coding to managing teams of developers?

Because of my work building search algorithms and Amazon's first web service (the search engine), Jeff Bezos asked me to become the chief technology officer of A9.com and help build our first distributed engineering office in Palo Alto, CA. I continued working at Amazon, launching a long line of services and features including Search Inside the Book, A9.com, and Amazon Mechanical Turk. That’s when I transitioned from being a developer to being a manager of technologists. The biggest challenge was that I had to change my internal reward system from "I did this!" to "My team did this!" That said, I had been writing software in some form for 30+ years, and it was time to learn a new skill.

What sorts of positions have you sought out throughout your career?

Since Amazon, I have worked at Google, Nordstrom, Allen Institute for Artificial Intelligence, and Pinterest helping build teams that create new and compelling services for users. The common threads between these companies are that they are passionate about their customers and they are looking to create groundbreaking services that innovate for them.

What excites you about working at Pinterest?

Pinterest as a business reminds me of Amazon circa 1998. It is full of energy and working toward its mission to help people discover and do what they love. Pinners come to Pinterest looking for new ideas, and if we can match them to a relevant idea, including advertisements, they win, the brand wins, and we get to keep both Pinner and partners. Rather than having ads be a distraction to the Pinner experience, we are investing in sophisticated relevancy algorithms to help get the right Pins, both organic and promoted, to the right person.

What do you spend the majority of your workday doing?

As a senior leader at Pinterest, I have three roles, and I love each of them. First, I support a team of 20+ engineers creating tools for our ads, search, and machine-learning efforts. Second, I work with our senior engineering staff, HR, recruiting, and our diversity and inclusion teams to create an environment where engineers can see themselves building a full career. Third, as the site lead for Pinterest's first distributed engineering office in Seattle, I help create a physical environment and local culture that feels like Pinterest. If you looked at my calendar, you would see 1:1s, several daily stand-up meetings (brief status updates), coordination meetings, and project reviews. Read between the calendar entries, however, and you’ll notice every interaction is structured to get people coordinated and moving in the same direction. The majority of my day is spent guiding projects forward.

How do you stay productive, especially with all of those meetings?

I keep a predictable schedule and honor my out-of-office time. During the week, I get in 30 minutes earlier than the team to catch up on the previous day, and then I leave at a predictable time so that my friends and family know when I will be available to spend time with them. This pattern allows me to work hard during the week and take the weekend to recharge so that I can rinse and repeat.

What do you appreciate most about your job?

My most memorable moments have come when my teammates and I have been able to launch something and celebrate what we’ve created together. There are so many different projects, teams, and companies to which talented people can dedicate their time, and I feel grateful and appreciative that these awesome people are choosing to make an impact together.

Read: Pinterest’s Head of Diversity: ‘This Is Not A Volume Game. Diversity Is Really Hard’

How have certain candidates stood out to you (in a good way) during the hiring process?

I look for two specific traits. I seek out candidates who think about success in terms of the end user/customer. Whatever the problem, it gives me confidence that this person would work out a complete solution, as opposed to just a tactical answer. I also look for an innovative spirit. I appreciate it when candidates are willing to put in work and come to an interview with a fully formed idea of what progress might look like in the context of what we’re discussing.

What have you read recently that you’d recommend?

I recently read a research paper called "Ambient belonging: how stereotypical cues impact gender participation in computer science." I love the paper because it brings to light an important reminder of the impact of physical space and environments have on feeling like you belong. It’s crucial to create a psychically inclusive environment if we want to attract diverse talent.

What advice do you wish you could have given yourself on day one of your career?

Deliver on your work and make friends. When you deliver, the people you work with will begin to rely on and trust that you can address increasingly interesting and complex problems. Friends will remember you when they go onto their next project, team, or company, and they will seek out the opportunity to work with you again.

Pinterest is a Jopwell partner company

Images courtesy of Sarah Takako Skinner