Working in Start-Ups: Insights from Alumni

By Michele Rapp

Start-ups are rooted in innovation—striving to fill product gaps, build something new, and grow rapidly. But the startup life is not for everyone! It requires a tenacious and scrappy spirit, hard work, a high-risk tolerance, and an ability to stay ahead of the curve.

Alexis Brinkman, SSH’14, and Zack Williamson, AMD’14, met while working at The Grommet, an online marketplace and product discovery platform focused on makers, inventors, and small businesses.

Alexis was the third hire in the wholesale department at The Grommet. In five years, she moved from merchandizing consultant to director of account management, all while launching product categories, drastically growing sales, scaling up processes, and building teams. Her Northeastern degree in anthropology and international affairs boosted her soft skills while her writing background became an asset for customer communications and brand articulation. In November 2020, Alexis became the director of operations for ReElivate, a new platform that hosts virtual experiences.

Zack spent over four years at The Grommet, building strategic partnerships with makers and managing accounts for the Wholesale B2B operation. Communication is key for this startup professional. With a BA in communication studies and four-years experience as a men’s varsity rowing coxswain, Zack found his career path. In November 2020, he became a Tech Touch Customer Success Manager at InsightSquared, managing communications across the customer journey.

Alexis and Zack live and breathe start-up culture and we asked them what it’s really like.


Alexis: I like the collective ownership of success and the accountability. Start-ups help you build skills for your portfolio. You can accelerate quickly if you’re good at what you do—I became the manager of a team of eight sales people in a short timeframe. You might end up eliminating your own position! Start-ups are not hierarchical and working hard is not the same as overworking.

Zack: The opportunity for reward is great. There’s a sense of satisfaction and accomplishment from building something with others. It’s fun and fast and you’re in the trenches solving complicated problems.

Working in a start-up with 20 people or less is a special experience. There’s a lot to be learned and my colleagues have interesting backgrounds. I developed a very broad professional network, with lots of varied industry connections. The high turnover of start-ups leads to having a large network. At one point I was hired by a previous co-worker, who I had met during co-op, eight years earlier.


Zack: The hours are long. There’s a tendency to always be “on” with Slack. There is high turnover. You are hired to solve a problem and the problems—as well as the business model—can change quickly and frequently. Uncertainty can be scary at times and it’s important to be comfortable with change.

By working in an early stage company, I was a generalist, doing everything that was needed, and it was a great experience. Early stage start-ups appeal to generalists. After six years, I felt the need to specialize within a role.

Alexis:  There is risk and the possibility of becoming unemployed—due to an acquisition, for example—but it’s not as scary as it sounds. I’ve learned that I will be fine, even after a job ended.


Alexis: Start-ups focus more on what individuals bring to the table, rather than an exact skill set. Think about what your “lack of” related experience could offer, such as a fresh perspective on problems. They seek people who can pivot duties and departments easily. Start-ups want novelty and freshness in employees. Your passion and hunger matters! There is less focus on job titles.

Zack: Early stage companies want to know about your ability to adapt and be resourceful in solving problems. Mid-stage companies are interested in rapid problem solving.

May 5, 2021

Alexis Brinkman, SSH’14


Zack Williamson, AMD’14



Zack: Organizational culture comes from the top. Learn about the founders and what they stand for. It’s not just about their ability to raise money. Look at the diversity of the staff and assess the company’s commitment to diversity.

Alexis: Find out about their goals and practices. Is their approach a fit with your values? Ask about their hiring strategy regarding diversity and what kinds of support they offer employees.


Alexis: Ask yourself: What am I going to learn? Who is going to support or mentor me? Does my manager have management experience? What are the goals and plans regarding funding? Are there plans for acquisition or going public? Where does their funding come from? What are the expectations around work hours? (You can ask about the typical hours for using Slack to gauge this). How do you communicate in the organization? What is the preferred mode of contact when there’s a product problem?

Zack: Ask about the organization’s access to capital and how long they can survive with their current funding. Who is backing the organization and by how much?


Built in Boston
Built In

Start-ups offer unique, exciting and valuable opportunities to have an impact and advance your career. Consider whether they might be right for your next job.