Real Young Women on the Job: Jessica Webb
Jessica Webb is a Massachusetts native through and through. She went to college at BU (go Terriers) then worked at the Apple store teaching workshops. A passionate traveler, she moved to Brazil for a year to teach English before eventually coming back to Boston. Jessica now works at Trello doing content marketing and working closely with their sales team. Previously she was at HubSpot and worked in customer support and on the marketing team for two years. Check out our conversation below!
-What is your 140 character resume?
I love working with customers. I’ve done support, sales, marketing, the common thread is understanding the individual on the other side and speaking to them in a way that identifies their problem, elevates their situation, and offers a solution, all while being very human-focused.
-It’s Friday at 10:00 AM – where are you and what are you doing?
Drinking coffee and reading over the Trello “Company Overview” board (piped into Slack) where all of the Trello teams provide their updates from the week (while listening to The Weeknd or Alt-J) while sitting at my desk where I work from home.
-Would 22 year old Jessica be surprised about where your career has taken you? Are you doing exactly what you thought you’d be doing?
I think she would be surprised. 22 year old Jessica wanted to move to California and create ads for Apple. The whole digital marketing world has exploded in the last 5 years. When I first graduated from college the difference between advertising and marketing was still fairly vague, now I truly work as a marketer for a saas company, and that’s been a totally unexpected (and awesome) experience.
-Work/life balance: "bulls**t" or "believe in it?"
It’s totally possible, but it takes a lot of effort. It’s something I’ve only recently learned how to do and it means getting over FOMO and knowing when to stay for a beer and when to go home/go for a work/take care of yourself.
-What’s the worst interview question you’ve ever been asked?
Overall I’ve had pretty good interviewing experiences. I’d say the worst things I’ve been asked have always been related to overly personal details. Once I started interviewing people I learned how much you are not allowed to ask about and looking back, I’ve definitely been in some situations where barriers were crossed. I feel really strongly that screening candidates for “culture fit” is a very shaky ground to stand on, it can quickly become, “would I want to have a beer with this person?” and as soon as that’s the case, you aren’t unbiased and that person is at a disadvantage. The more I work and the more places I’ve worked at, I realize that the best person for the job is the one with those skills, other things fall into place, but generally if you possess the specs for a job and aren’t an asshole, that’s all that should really matter.
-Talk to me about mentors: have you ever had one? Would you ever take on a "mentee?"
I’ve had many and think they’ve been crucial to my career development. I would and have definitely taken on mentees, it’s a great way to pay it forward and learn a lot about yourself. I have taken on quite a few mentors at my alma mater, and even helped one get a job at HubSpot (where I used to work)!
-What’s your proudest career moment to date?
Starting and growing HubSpot’s Instagram to over 30,000 followers. I never thought people would care so much about a marketing software company’s “behind the scenes” culture.
-Do you believe in a dream job? If so, what is it?
I think a dream job is one that aligns with your personal values. I love what I do because I truly believe it’s helping people, it may not be humanitarian work but a lot of incredible organizations do great work every day using our product, and I’m truly proud to be a part of a team that empowers those teams.
-What B2B or B2C brand is your favorite to follow on social media?
LL Bean because it’s basically nature porn and is especially pleasing when I’ve been sitting inside for too long!
-What do you love most about the digital scene in Boston?
There are so many young and intelligent people in Boston, but the tech community is incredibly humble. I love how approachable the leaders are and how many meetups and events are always happening. I also love the juxtaposition of Boston being such a historical and “old” city.
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