Thriving at a Startup with Lauren Sherman of Shyp

  • Copy by: Caitlin Timson

Lauren Sherman’s first lesson in marketing came early in her career: Be passionate about what you’re marketing. When her first job out of college (in telecommunications) left her feeling less than fulfilled, she turned to the Internet for answers and opportunities. A Craigslist ad led her to her first experience in the startup world as Zipcar’s marketing coordinator in Washington D.C. “Zipcar was the first place I worked where I formed a deep connection with my coworkers, which taught me how important it is to work with like-minded individuals.”

Bitten by the startup bug, Lauren transitioned to a social media role at TaskRabbit. By the time she left three years later, Lauren had led its expansion into nearly 20 markets across North America and spent a year in London launching and growing its first international market.

The opportunity at Shyp came unexpectedly during Lauren’s time in London. Upon meeting with the CEO and learning the company’s mission to radically change the shipping industry, Lauren dove into her current role as vice president of marketing when she returned home. She has led the company through a major rebrand, as well as witnessed the transition of Shyp’s couriers from 1099 contractors to W2 employees.

She’s here on The Everygirl to spill more about knowing when it’s time to transition to a new company, the traits she looks for in a potential team candidate, and the biggest misconceptions of working for a startup.

Name: Lauren Sherman
Location: San Francisco, California
Age: 29
Current title/company: VP of Marketing, Shyp
Education: Bachelor’s in communication from Lynchburg College

Tell us about your first job and how you landed it.
Right after graduating college, I landed a job with telecommunications company I had previously interned with. After a couple of months on the job, I learned first-hand that in order to be personally fulfilled as a marketer, it’s important to have passion for what you’re marketing. It became clear that telecomm wasn’t for me and, like so many recent college grads, I turned to Craigslist, which led me to ZipCar.

You have worked with some incredible names in the startup world! Let’s start with Zipcar. Tell us about how you landed the position and what it entailed.
I first learned about ZipCar on a roadtrip with my sister. I remember seeing a sticker on the back of a car that said “Wheels when you want them,” which immediately sparked my interest. Keep in mind this was 2007, before mobile and location-based technologies—apps were not yet a thing.

A couple of months later, while browsing Craigslist for jobs, I found a listing from Zipcar for a marketing coordinator and immediately applied. Luckily, this was before needing to stand out as an online applicant, and within 48 hours I had my first interview. Never in my life have I walked into a room and connected with everyone so quickly. I knew right away that not only was Zipcar a perfect fit for me, but tech in general was going to become a passion of mine.

The position was a local marketing role, tasked with growing the user base of Zipcar in Washington, D.C. I was given a lot of autonomy to come up with new innovative ways to market the service, which I loved. Zipcar was the first place I worked where I formed a deep connection with my coworkers, which taught me how important it is to work with like-minded individuals.

Next, tell us about your time at TaskRabbit. How did your career grow with the company while you were there?
I like to think of my experience at TaskRabbit as the bootcamp that prepared me for where I am today. I joined the company in a social media role and by the time I left, I had led its expansion into nearly 20 markets across North America and spent a year in London launching and growing its first international market. I learned the power of flexibility, and how essential it is to be open to trying things I’d never done before.

When I was approached to launch London, I had never expanded a company into a foreign territory, nor was I familiar with the London business and technology environment. I didn’t feel anxious about that, though. Instead I was fueled with excitement to try something new. This concept—not being scared to try something new—is a really important value of mine, and something I try and remind my team as much as possible. It’s thrilling to be surprised by your own capabilities—sometimes they just need to be unlocked.

It’s thrilling to be surprised by your own capabilities.

Now let’s talk about Shyp! How did you land the opportunity to run Shyp’s marketing team? What are your main responsibilities? Tell us about your typical work hours.
I first learned of Shyp when I was living in London. Kevin, our CEO, reached out to me for a casual conversation about marketing and marketplace businesses—we’d been connected by a mutual friend. I wasn’t looking to leave TaskRabbit, but after meeting Kevin and seeing his passion to radically change an industry in dire need of innovation, I became obsessed. A couple of months later I returned to the States and Shyp was in need of someone to build its marketing framework from the ground up. I dove right in.

I oversee strategy and execution for customer acquisition, partnerships, growth, and branding. My team consists of a brilliant group of people who individually specialize in an important aspect of Shyp’s business—content, social media, partnerships, design and branding, and PR. We’re still a small company, so intentionally I hired a team of experts who, when the time comes, will build their own teams underneath them.

My hours vary greatly depending on the specifics of the work and the needs of my team. I spend a couple days a week in the trenches with my team to make sure we’re staying connected and they have access to me for whatever they need. The rest of the days are spent on strategy and ruthlessly fighting to keep myself at email inbox zero.

Are there any misconceptions, you find, that people have about working in the startup world?
Some people think working at a startup is all fun, all the time, with days full of free food and ping-pong tournaments. Sure, technology companies offer unique perks to their employees, but working at a startup is very challenging.

In most cases, as a startup employee, you’re openly and proudly trying something that’s never been done. It takes a tremendous amount of commitment and a fundamental belief in what you’re doing and passion about the problem you’re trying to solve. It’s easy for some to see perks as a reason to join a startup, but if you lack the commitment and passion, you won’t last very long. The days are often long and stress levels high, but when the team accomplishes something they’ve been working on, it’s all worth it.

When deciding to take a new position or move to a new company, how do you know if it’s the right fit? Tell us about the motivating factors behind the desire for change and the job search process.
I always trust my gut, particularly when it comes to people. It’s very important to trust and get along with those you work with, particularly during stressful periods. It’s easy to get wrapped up in the idea of a company, but if you don’t believe in the people who serve as the foundation for it, you’ll hate it. And of course, if you aren’t passionate about what the company does, don’t even take the interview.

When people ask me for advice on when to look for a new job, I ask them if they feel passionate about what they’re doing and if they feel challenged every day. If they don’t, it’s time to seek something new.

…if you aren’t passionate about what the company does, don’t even take the interview.

Does your formal education apply to your current career? 
I have a degree in communications and my job, of course, requires me to be able to effectively communicate. But the core responsibility of the team I lead is customer acquisition and there isn’t a degree for that. Marketing degrees do not necessarily instill the skills needed to build and sustain a business, particularly in today’s technology climate.

I’m a huge believer in learning by doing. I am where I am because of the work I’ve done, not where I went to school nor what I studied.

What are the key traits you look for in interview candidates when growing Shyp’s marketing team?
Humility, passion, and empathy.

What have you found to be most effective when it comes to successful leadership?
At Shyp, we really value humility and empathy. We check egos at the door and operate as one team. When you’re working at a fast-paced, high-growth company, it’s important to operate in an environment that makes cross-functional work something to look forward to.

I am where I am because of the work I’ve done, not where I went to school nor what I studied.

What have been the biggest challenges you’ve faced in your career and how were you able to overcome them? What are the greatest rewards?
I’ve worked at differing companies, but the majority of them have a foundational goal of making people’s lives easier. ZipCar makes it easy for anyone with a license to rent a car. TaskRabbit helps connect people with those nearby who can help get something done. And Shyp is completely re-imagining the shipping experience from the ground up to save individuals and businesses time and money. All three companies are innovative, and also tremendously hard to build. I’ve spent the majority of my career finding ways to change consumer behavior by introducing them to a new concept. It’s not easy, but I know that I’m making a difference.

At Shyp, I get out of bed every day knowing that I’m a part of something that’s really helping people. We hear stories every day of how people have used Shyp to make life easier or build a business. That’s my reward.

Take us through a day in the life of Lauren Sherman.
In the morning you can find me doing circuit training (6 a.m. shout out to JGfitSF [] for kicking my butt!). I then have breakfast at home and head to the office. I reserve 9:30 a.m. to 4:30 p.m. for meetings and spend 4:30-8:30pm doing work/answering emails. I then break for dinner—either with friends or I cook at home with my boyfriend. Then, Netflix.

Never be afraid to ask for what you deserve.

Best moment in your career thus far?
I am proud of so many things I’ve been fortunate enough to be a part of, but the transition of Shyp’s couriers from 1099 contractors to W2 employees and our recent rebrand are top of mind.

What advice would you give to your 23-year-old self?
Never be afraid to ask for what you deserve.

Lauren Sherman is The Everygirl…

If you could have lunch with one woman, who would it be and what would you order?
If I could have lunch with one other woman it would be Beyonce. (No explanation needed.) I’d order BBQ ribs because they’re delicious.

Morning ritual?
Exercise and coffee.

Best part of living in San Francisco?
So much to do in such a small area. I can go on a trail run, hit the beach, visit a museum, admire Redwoods, and check out a brewery all in the same day.

Happy hour drink of choice?
Dirty martini or a glass of pinot noir.