Lead(H)er Profile - Jess Dashner, Director of Media Strategy & Operations at Gupta Media banner image

Lead(H)er Profile - Jess Dashner, Director of Media Strategy & Operations at Gupta Media

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Our Lead(H)er series features impressive women leaders in the tech industry. In this Q&A, we are featuring Jess Dashner, Director of Media Strategy & Operations at Gupta Media.

Where did you grow up and how would you describe yourself as a child?

Growing up in Trumbull, Connecticut, I loved learning: learning how other people think and act, learning new things in school, learning about the way the world works and my place in it. If you asked me my favorite school subject as a child, I would have said “all of them.” I wanted to be free to explore all potential subjects, including the ones I was less “naturally inclined” to excel at (I’m looking at you, gym class).

What did you study in college and what was your first job out of school?

Throughout my four years at Boston University, I explored many different potential paths, eventually landing on Psychology, Advertising, and Statistics. After gaining much-needed perspective from internships that spanned agencies, in-house marketing roles, and start-ups, it became clear that I was looking for a role that would combine the versatility of agency life with the challenges of working at a small company that would teach me how to build a successful business, not just work for a successful business. This led me to Gupta Media, which, at the time, was a recently established Cambridge-based digital marketing agency that primarily focused on managing search engine marketing campaigns for record labels. Believe it or not, I’m still there 14 years later, though my role and the agency itself have both evolved immensely since those early days.

Can you share the details on your career path and what were the critical moments that got you to where you are today?

I know that my path has been fairly unique in that I have been with the same company throughout my career. When I started at Gupta Media, I was an individual contributor, responsible for day-to-day campaign management. The first critical moment in my career was one that our agency’s Founder, Gogi Gupta, still remembers fondly every time employee annual reviews roll around. It was the first real performance review of my career, and I went into it expecting the professional equivalent of what I’d come to expect from years of straight A’s in school: put in the work, get the top grade. Needless to say, my review was lackluster at best, and I was left confused and disappointed. It was then that I learned effort isn’t enough in the real world. You need to be able to deliver results and self-promote. Keeping that early lesson in mind, I developed my skills and formed deeper relationships with our clients. This led to more autonomy and bigger opportunities. Early in my career, earlier than most, I was given my own team to manage, along with my own roster of clients. I had just returned from a few months working out of Sony Music’s office in London. I’d just crammed a lot of life experience into a short period of time and was about to embark on a completely different type of professional journey. This was another pivotal “sink or swim” moment for me and one that I’m glad I dove into head first, as it was a very important piece of my journey to where I am today.

What is your current role and responsibilities?

Today, I am the Director of Media Strategy & Operations at Gupta Media, as well as an Account Director within our media department. This position allows me to assume two different roles at once. As Director of Media Strategy & Operations, I help ensure that our immensely talented media department has everything they need to deliver best-in-class work for our clients. This spans a variety of responsibilities, from managing partner relationships, to guiding training and career development, from working across departments to determine agency strategies and POVs, to making sure we’re the first agency to test new opportunities in performance marketing. As Account Director, I oversee our relationship with several of the agency’s top clients while also pitching and onboarding new business.

Looking back, is this where you thought you’d be professionally?  Was it always your goal to be in this position?

I still can’t believe that I’ve been with the same organization since I was 21 years old. To be completely candid, I’ve often wondered if I’m missing out on the more holistic perspective that I could have gained from bouncing from company to company. However, I would have had to sacrifice all of the invaluable experience that comes with growing a successful business over many years of innovating, scaling, and learning. So to answer the question, no this was not where I expected to be in 2022, but it was always my goal to be a valued member of the leadership team at a cutting edge, ever-evolving company.

For people who are looking to be in a similar position, what advice would you give to others in terms of helping them achieve their career goals?

  • Be hungry, be curious. You can’t move forward in your career unless you’re jumping on every good opportunity that comes your way, and you can’t prove that you deserve those opportunities unless you’re asking the questions and doing the research that it takes to turn those opportunities into success stories.​
  • Start your career at an agency. Agencies allow you to work with a diverse group of clients, industries, and personalities very early in your career. Bonus points if you work at a small agency, where you will also likely work across departments and assume different roles at the same time.
  • Advocate for yourself. As I learned at my first performance review, it’s not enough to work hard and quietly do the job well. You need to make sure your achievements are getting recognized, and you need to stand up for yourself if you’re getting passed over for opportunities that you’ve earned. It’s not always comfortable, but it’s important.
  • Try, fail, learn, repeat. We learn from both our successes and our failures. It’s important to stay nimble and accept that there’s always more to learn.

What are the most important skills that you need to do your job well?

  • Adaptability. Marketing, particularly digital marketing, is an ever-changing industry. If you can’t learn to reprioritize, pivot quickly, and learn without an instruction manual, then you fall behind.
  • Empathy. My job is part client consultant, part team leader. You need to understand where a person is coming from and where they want to go in order to help them on that path.
  • Organization. It might sound like a basic skill, but when you’re part of a team, you can’t afford to be disorganized and unreliable. An organized mind can provide clarity for everyone.
  • Self Awareness. It’s important to lean on your strengths, know how you like to manage and be managed, and be authentic to your own personality. You can fake it ‘til you make it to a certain extent, but at the end of the day, you need to be the best version of yourself to succeed on your own terms.

What do you find most interesting/rewarding about your work?  What’s the most challenging?

Managing people is the highlight of my work. I love being a part of someone’s success story, helping them tackle a challenge by teaching them how to think through a problem rather than dictating  each step to take to solve it. It’s very rewarding to see someone achieve their professional goals, both while they’re at Gupta Media and wherever life has taken them after.

There is never enough time to achieve everything I want to achieve, and sometimes there’s barely enough time to achieve the bare minimum. The same is true for my team, and even for my clients. I’m always wary of burnout, relationships becoming transactional, and sacrificing what is best for what is fastest/easiest.

What is your proudest professional accomplishment?

A few years ago, Harvard Business School selected Gupta Media to be the subject of a case study that examined our unique approach to performance marketing. I worked closely with HBS to discuss our work, as the case delved into the projects that I had personally overseen in my role as Account Director. When the case was ready to be taught to all HBS first-year MBA students, I was invited to lead a Q&A session in one of the classes. It was a true honor to stand in front of some of the brightest minds from around the globe, acting as teacher rather than student.


What do you enjoy doing in your free time?

In addition to spending time with my husband and 2-year-old son, I love to walk and run outside, play board games with friends, and eat my way through whatever city I’m in.

How do you manage stress?

A little stress can help get the job done, but a lot of stress isn’t good for anybody. For me, perspective is important. Sometimes, I need to take a step back, look at the situation from a different perspective, and give myself a moment to react without actually acting.

How many cups of coffee do you have in a day?

Current answer: 1-2 cups per week. Plus, I love tea. However, ask me again in a couple of months when I have a newborn and a toddler on my hands.

Any book or podcast recommendations? 

I love the Intelligence Squared U.S. Debates podcast because each episode takes a debate topic and invites highly regarded experts and thought leaders to debate their opposing viewpoints with each other. It’s a great way to learn more about certain subjects, while challenging yourself to approach the debate with a truly open mind that can be changed if the case is compelling enough.

What advice do you have for recent college graduates?

Seize every opportunity you can. Say yes to everything (within reason). If it pushes you out of your comfort zone, even better. Some of the best opportunities are ones you need to ask for, so don’t wait for them to be offered to you. And when you do ask, make it easy to get that “yes.” You might not be ready to take the lead on a juicy new account, but you’re ready to listen in on the pitch or help the team with research. These will all be valuable learning experiences early in your career, so be a sponge.

About the

Gupta Media is a performance marketing agency, founded on the idea that advertising creates huge leverage for our clients.

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