In our series “Jump-start Your Job Search,” Bostonia brings you short interviews with BU alums who are leaders in their fields, such as banking, advertising, tech start-ups, journalism, or nonprofit organizations.

They talk about how they got to be where they are and what they’ve learned from their mistakes. They tell us what they look for when hiring and offer advice for those just embarking on a career.

Dana Levin-Robinson (Questrom’10) engineered her own career transformation, from account manager at a New York advertising firm to chief of staff at healthcare start-up VirtualHealth, a technology company that offers software and services that help insurance companies, health plans, and healthcare providers manage patient costs.

Levin-Robinson joined VirtualHealth in 2016 as its marketing director, but took advantage of opportunities within the company to take on new responsibilities in business development and operations, broadening her skills and expertise. She attained her current position as chief of staff in January 2018.

Today, 30-year-old Levin-Robinson, who has an MBA from New York University’s Stern School of Business, oversees four departments, public relations, business development, operations, and human resources, at the company, which was recently named one of North America’s fastest-growing companies by Deloitte. VirtualHealth intentionally hires people from outside the healthcare sector, she says, because it wants to build a team that “thinks beyond the limits of our industry.”

Bostonia spoke with Levin-Robinson about how she became interested in the healthcare industry, the qualities she looks for when interviewing job candidates, and what she’s learned from her experiences along the way.

Bostonia: When did you know that you wanted to pursue a career in healthcare?

Levin-Robinson: I actually didn’t. I accidentally fell into healthcare when I started working at an advertising agency that was exploring how to transition Pfizer prescription drugs to over-the-counter. As I learned more about the industry’s challenges and how technology can solve them, it was a no-brainer to keep working in the space.

How competitive is the healthcare industry, and what advice would you give new graduates interested in careers in the field?

I would say tech is tricky to enter because medium-to-large companies often require a very specific expertise (e.g., acquisition marketing vs general marketing), and that’s hard to break into as a new college graduate. Smaller companies often scare new graduates because of their instability: you never know if the job or company will still exist in a few years. I strongly recommend focusing on post Series A companies, which have a cash influx to hire more employees and need a balance of junior and senior people to get the work done.

What are the qualities you look for in the people you hire? Are there deal breakers?

I work at a growth-stage company where everyone wears many hats and has to be willing to help out regardless of the task, so we focus on hiring people who are resourceful, ambitious, and team-oriented. The deal breakers are often those who are very stuck in the “but it’s not my job” mentality and who struggle with the uncertainty a growing start-up faces.

What kinds of questions do you ask during an interview?

I ask about each candidate’s previous successes, but I care just as much about how they handle failure. I’ll ask questions like, “How did you handle your last big mistake?” to assess how flexible candidates are at solving problems and thinking on their feet. Autonomy is also important, so I always explore what kind of manager the candidate likes to work for and what company culture helps them thrive.

What are some common mistakes that young job candidates make?

A common mistake I see is not having any questions for the interviewer. I work at such an innovative, exciting company that I can’t understand how someone doesn’t have 100 questions about it. A lack of questions shows a lack of research and signals someone who isn’t enthusiastic about the role or the company.

What advice would you give an employee for the first day on the job, and for the first six months?

On the first day, I would recommend an employee try to learn as much as possible about the company, the product, and the teams. It’s really important to understand how one’s role fits within the overall company and its goals, especially if that company is young.

By six months, a new employee should feel comfortable proposing new and better ways of running the team, whether it’s big new projects or small operational changes. The reason I oversee my company’s business development is because nobody was focusing on that work, and I took initiative in planning the objectives and a roadmap for the department.

Are there mistakes you’ve made in your career, and if so, what lessons have you learned from them?

Absolutely—anyone who says they haven’t made any mistakes is lying or clueless. When I looked to transition from advertising to tech, I admit I could have done more research. I was very unfocused about the type of work I was looking for, and that was very obvious in my early interviews. I specifically remember an interviewer asking me what kind of marketer I wanted to be, and I responded, “Whichever kind you need.” That’s a terrible answer. Companies look for a point of view, regardless of how junior a role is.

Who has had the greatest influence on your career—teacher, colleague, boss, family member—and what did you learn from that person?

My parents will always get the credit. Both are incredibly smart in different and complementary ways. My mom taught me to “be smart, not right,” which is timeless advice for both work and personal situations. The obvious choice may not be the most politically savvy—you have to think through the consequences of what you’re doing. My dad taught me the value of hard work and that nothing comes easy. If anything, life gets harder the more senior you get, so you have to build up your tolerance for frustration.

Are you an alum who would like to be interviewed for Bostonia’s “Jump-start Your Job Search” series? Email John O’Rourke at orourkej@bu.edu.

Read other stories in our “Jump-start Your Job Search” series here.