October 2, 2018

Career Path: Elaine Milardo, Senior Director, Data Platform at DraftKings

What does the career path and a day-in-the-life look like for a Senior Director, Data Platform at DraftKings?

We interviewed Elaine Milardo to find out!

Where did you grow up?  What was your very first job (either pre-college or internship)?

I grew up in Middletown, CT and Wethersfield, CT. I have a huge extended family (25 first cousins). I think the last name “Milardo” took up about half of the phone book in Middletown! It was amazing growing up in a small town where everyone knew the family.

When I was in middle school, I was a papergirl delivering the Hartford Courant, on foot, around my rain, ice, and snow.  I think it’s where I got into the habit of getting up before dawn and acquired my aversion to the cold. I also worked as a cashier Sears for many years during high school and college.  I really enjoyed retail. I’m an extrovert and learned a lot about how to be a good manager from watching my supervisors at Sears. For example, on a busy holiday evening, the manager of the store came down to my department and worked the registers with us for hours, regaling us with stories. That stuck with me - he wasn’t above jumping in and helping out his team while bringing the positive vibe.    

You graduated with a Psychology degree from Smith College.  How did you get into the tech industry?

Like many, after I graduated, I didn’t know exactly what I wanted to do. I wasn’t sure I wanted to continue on with graduate school and was eager to start working (and my parents were also eager to have me start working!). I was able to focus on a few things that I knew I wanted in a new job.  I wanted to work in the Boston area, at a startup, in a field adjacent to psychology or medicine, just in case I wanted to revisit the decision on pursuing an advanced degree. I was fortunate to find an opportunity with a startup that focused on conducting a meta-analysis of clinical trials for pharmaceutical companies. Twenty years ago, those studies were reviewed and compiled, prior to analysis, manually. So, I spent a lot of time mastering a photocopier at the Harvard Medical Library!  On the flipside, though, I was introduced to methodologies behind consolidating, cleansing and preparing data in order to enable the statisticians to run their data models.  In essence, at a much larger scale, that’s what I continue to do today!

Your career has been centered around data. What is it about working with data that has been a passion for you?

In my first job, I was able to have a significant impact on the efficiency and value of the business by wrangling data - as an entry-level assistant research analyst! That was powerful and motivating to me, especially at that point in my nascent career.  After that first role, it helped me define and focus on what I enjoyed doing at work. I began studying and learning more about data engines, administration, transfer processes, design principles, reporting and delivery tools, and analytics use cases. I took classes, read a ton, developed, and, eventually, got an entry-level data warehouse job at AT&T working on their local AdSales warehouse.  In each of my roles, with the mentorship of highly skilled data technologists and really good managers (I’ve been exceedingly fortunate), my technical skill set grew and I was able to take on designing more complex and large-scale data infrastructure.  

The data industry is dynamic; there is always something new to check out and dig into.  It could be a new design pattern to consider, a new storage engine to test, a new way to deliver or visualize data or a new data product to build or iterate.  

To distill it, I love being able to create a platform that enables folks to more easily diagnose, discover and action data.  I love working with a broad set of teams to make finding that value, easier. And, finally, I love working in an industry that is never stagnant.  I’m never bored.

How has the use of data evolved in terms of its ability to drive businesses forward since you started your career?

When I first started my career, it was typical to have a small database that was updated, with few transformations, nightly. Analysts leveraged the data to see what happened and, potentially, did some diagnostic work into certain patterns or trends. They would run database connected spreadsheets or direct data queries. The users were specific to teams like Finance or Operations.

As the accessibility of the data changed, the user profile changed. Data wasn’t just for a specialized team or users. There was a push to democratize data to the broader population of an organization. Everyone needed access to self-serve reports, dashboards were pervasive and intraday updates were essential for improving operations.

Data volumes continue to balloon. Near-real-time batch and streaming are now essential. Descriptive and diagnostic analytics are still at the core, but enabling predictive and actionable insights through machine learning has become critical in driving better decisions.

Can you share the high-level responsibilities of your current position as Senior Director, Data Platform at DraftKings?

The Data Platform organization at DraftKings is made up of two amazing teams that I am grateful to lead: Data Engineering and Data Science Engineering. On the Data Engineering side, we are responsible for designing, developing and managing the data infrastructure at DK.  We are the builders and plumbers - we assess data sources, build pipelines, design data stores, transform data, enable a variety of delivery methods, ensure governance and support the users of the infrastructure. These folks are a keystone in enabling our wide-ranging data capabilities.

On the Data Science Engineering side, we are responsible for the creation of data products.  Our Data Science Engineers are just that...they are software engineers with excellent quantitative skills. They leverage both of those skill sets, extensively, and are responsible for the curation of a portfolio of data products ranging from personalization and recommendation engines to customer modeling to fraud detection. These folks are essential to realize and achieve value from our data.

I’m responsible for leading and managing these teams and enabling and supporting our technical leaders in creating a scalable, speedy, and well-architected data environment.  I spend time in planning organizational roadmaps that align with DK’s strategy and I work closely with our Product folks to help drive product vision through specific initiatives and projects that can be implemented in a highly iterative fashion

Tl;dr:  I get to do both technology and management and it is awesome.

Day in the Life

Coffee, tea, or nothing?

Coffee.  So much of it.

What time do you get into the office?

I’m a morning person that likes to ease into the day.  I’ll get up around 5:30 AM, make a coffee and hang out at my kitchen table with my cats and my laptop.  I’ll catch up on email, review my calendar and prepare for meetings I have that day. Once I get into butt isn’t in my chair for more that 30 minutes a day, so this is my time!  I end up heading in around 9-9:30 AM.

What are three things that motivate you in your role?

I love mentoring and coaching. I have strong satisfaction with seeing others grow and achieve their goals.  It seems trite, but it’s been an evolution over my career. I used to be a kick-ass individual contributor and felt successful when I personally delivered awesome stuff.   Fifteen years ago when I started managing, I stepped away from IC work and shifted my worldview. It’s common, of course, as you grow as a manager. I am successful (and feel amazing) when my folks succeed.  That is the biggest motivator for me. I’m a quintessential manager.

There are always new technologies out there for data.  Like many, I have to balance my desire to try a new data processor technology with successfully maintaining our existing infrastructure.  My folks are pretty effective in pushing me to let them try new stuff. My vocation, for many years, was data engineering. With the integration of data science engineering into data platform and the hiring of a fantastic head of data science and his team, I’m continually learning.

The Data Platform team has a huge, positive impact on DK.  Whether it’s, for example, providing a data product that increases revenue or reduces risk, or providing a data store that allows for both the rigor of a single source of truth and the flexibility of multi versions of the truth, our team is so valued and valuable at DK. It’s a good feeling and huge motivator to feel the love.

Every day is different, but can you outline what a typical day looks like for you?

I need to get myself organized before I get into the office.  I prepare notes or comments for each of the meetings I have that day and I should have a priority of tasks that I need to accomplish.  I’ll usually meet up with the technical director, leads and product, informally, each morning to catch up on their evening and if they have any potential concerns or issues.  Then, I’ll end up in meetings for most of the day. These range from discussions about new product dev, product, and technical planning, recruiting/interviews, 1-1s, or key technical design discussions.  I’ll usually end up walking around and checking in with the teams, again, in the afternoon and make myself available if folks want to quickly chat on a project, an approach, or anything that’s forefront of the mind.  At the end of the day, I’ll either be ready to go home or feel up for hanging out with people in the office, after work.

What time do you head out of the office?

I’m usually out around 6:30 PM. I’m social, so I do try to wind down the day with some good conversation with folks from around DK.  We have a bunch of after-hours groups or events at DK from D&D, board games, trivia or, even, karaoke!  My favorite (and I’m a bit biased since I started it!) is WhiskyKings, a bi-weekly get together where we do whiskey tastings (though we have expanded our portfolio to bourbons, recently). Just like I like to ease into the day...I also like to ease out of the day!

Do you log back in at night or do you shut it down completely?  

Yeah, me and Slack have been pretty tight in the eve.  With my wife’s encouragement, I’ve gotten better at putting down the phone when I get home so I can cook and chat with her about our day.

Any productivity hacks?

I try to bundle all my 1-on-1s and staff meetings on the same day.  I find that it helps me keep on schedule and allows me to be more focused on the conversations.

I do tend to move from one meeting to another.  Sometimes, though, I require uninterrupted time to just, well, think.  So, I secretly block off an hour during the day to focus on a particular problem or project.  I’ll leave it to my coworkers to try to figure out what hour that is...and attempt to book over it!  

What are the 3 apps that you can’t live without?

  • Slack - Because I don’t want to miss a thing
  • Spotify -  ‘Big Band‘ and ‘Deep Focus’ playlists
  • Starbucks - see above
  • (and, of course) DraftKings

What professional accomplishment are you proudest of?

In my previous job, I relocated to Europe and established corporate Business Intelligence teams in Barcelona, Spain and Winterthur, Switzerland. It was an amazing experience for me, professionally and personally. I learned so much about hiring, communication, and collaboration across regions and cultures.  I made meaningful connections with colleagues and friends whose expertise and judgment I value immensely.

Who do you admire or call upon for professional advice?

I’m fortunate to have excellent relationships with many of my current and former colleagues. The data community in Boston is relatively small, so it’s easy to stay in touch and keep up with everyone. I definitely have a few fellow data and management experts who I got to for professional or technical opinions.

My mother, father and sister are all incredible listeners and when I’m stuck on something I’ll run through different scenarios with them - just having that objective and balanced sounding board usually brings insight and clarifies the situation for me.  And I can always rely on my wife to help me work through scenarios; she’s a creative professional, and helps bring a different perspective. I am lucky to have a large pool of people to call on for valuable points of view!

Keith Cline is the Founder of VentureFizz.  Follow him on Twitter: @kcline6