How This RDV Alum became Employee # 1 at PillPack

This is the first article in a series of interviews with Rough Draft alumni discussing where they are now and how they got there.

Jacob Mulligan, RDV Team (’15), spent the fall semester of his 4th year at Northeastern balancing school, Rough Draft, and working at PillPack. He was a part of the Rough Draft Student Team that would decide to fund companies like machine learning platform Indico, aquaponic ecosystem Grove, and data driven parking solution Smarking. It was this semester that would shape Jacob’s decision to leave school and become the first employee at PillPack.

Jacob recounts when he first met the PillPack founders and made the transition. He was working at mentorship driven accelerator, TechStars, as a HackStar, an individual selected to work with a handful of TechStars companies throughout the program. Jacob first started building some of the first code for PillPack during the program. About half way through the program, he took a walk with one of the founders, TJ Parker. Casually, TJ dropped the question: “So, do you want to stop working for TechStars and just work for PillPack?” It didn’t take long for Jacob to realize, yes, this is what he wanted to do. Jacob spent that fall semester struggling to find a work-life balance:

“It was really enjoyful going from meeting with student founders, to working on code for PillPack, but really hard to manage. I generally sacrificed sleep, which I do not advise.”

When Spring course enrollment came around, Jacob quickly compared what he was learning at Northeastern versus what he was learning at PillPack. At that time, the company was defining their mission, core values, and applying to IDEO. At just five people, Jacob was in the center of all the action: “It was fun, challenging, and I was learning a ton.” As enrollment period passed, Jacob would officially join PillPack as Product Engineer, where focused on developing customer-facing tools such as sign-ups and dashboards, and eventually develop pharmacy-facing tools to help team members manage a queueing tool for managing workflow.

Looking back, Jacob describes this as a naive decision, stating,

“To be honest, I don’t think I really knew what a risk it was to be leaving. Before PillPack, I was at a startup that ended up falling apart and closing their doors. It totally sucks when it happens. I had done so much work there with so many team members who had poured their time into the company thinking it would work out.”

Not every company on PillPack’s trajectory continues to thrive, but a year later, this pharmaceutical delivery startup has raised $62M, grown to over 170 employees, and opened offices in New Hampshire and Boston.

“PillPack is growing like crazy from a customer standpoint. The biggest focus right now is supporting this growth and building tooling so that the masses of people we are hiring can be trained more quickly and have better tools to work with to ship to, onboard, bill, and support new customers.”

After the company’s year of rapid growth, Jacob advises us from his first hand experience on something that surprised him: the unavoidable change in culture as a startup grows.

“ When we went from two engineers to six to twelve, it shocked me just how obvious that culture shift was. As the first employee, you see every evolution of the company. Early on, I would go to dinner with the two co-founders regularly. I got used to being privy to all of the information that the company has to share. As we grew, it was just not possible for us to all talk about every aspect of the business. Every phase of the company has been really exciting. It is difficult to let go of the culture that came before, and embrace the one that is about to come. As a shareholder, you know it is the right thing for a company to grow, but as an individual it take some getting used to.”

At the end of the day, Jacob sees every vague problem he is handed as an opportunity. “Getting to spend a day or two at the pharmacy to get a handle on the processes involved at the company is always exciting. Working on challenging problems and translating that into a solution that is a combination of human process and software is what I really enjoy.”