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Challenges and Opportunities in Start-Ups & Large Companies

By: Tasha Drew, Senior Director of xLabs – VMware

Most career journeys are not straight, but take many different paths. I built my technology career working in Bay Area start-ups, but my path wound its way to my current position at a very large publicly-traded company. While they are very different in structure, both start-ups and large companies presented many opportunities and many challenges to me which helped me grow as a technologist, a leader, and a mom. 

Let’s start with start-ups. Start-ups are great incubators of new ideas and bringing innovative products to market. When I worked for start-ups, I felt like I was always working on cutting edge technology and learning many exciting new things. I had the chance to try out so many new skills, like product management or learning Ruby on Rails, simply because I was interested in them. We were always innovating, so it felt like I was literally living in the future when it came to technology. 

Unfortunately, there were also many challenges working at start-ups. While I got to learn new topics, being a fast learner meant I was often given more and more work, so I worked constantly. My knowledge in a subject was often doubted or downplayed. The pay was low and I had many toxic and retaliatory managers – some who actively forced me out of companies when I spoke up – and who were hired simply because of their relationships with the CEO. 

I was not a mother when I worked in start-ups, so I did not experience the same challenges that so many of my colleagues who had children at home did. I knew there were few accommodations for them, but I don’t think I realized the impact that had on them. Looking back, I realize I was often insensitive or flat-out rude to my colleagues who had family obligations. I didn’t like how the working mothers and non-working mothers were pitted against one another because of the endless workload and lack of support.

When I made the transition to where I’m working now, I was relieved to see alleviation of some of the challenges I faced in start-ups, like supportive managers, better pay, and a more balanced workload. Unfortunately, I noticed quickly that some of the same challenges remained. I started here just after I became a mother, and I had a really hard time during those first few weeks on the job finding mother’s rooms on campus. There weren’t even maps or directions provided during orientation! Shortly after I started, I flew to Barcelona, Spain for a conference, and my breast-pump broke on the plane there. I eventually found a hand-expressed one at a pharmacy, and then I had to trek for what felt like hours to the mother’s room in the conference center – which was a huge conference room with only partly-covered glass walls! Needless to say, it was not the best conference experience of my career. Thankfully, my company has greatly improved their accommodations and support for working mothers, but I still vividly recall the panic and frustration of my first week on campus having nowhere to pump.

Despite these challenges, the respect from my manager and peers that I feel in my current role is a night and day difference from start-ups. From the jump, I was given authority and trusted as a subject matter expert. Like start-ups, I’ve been able to explore many new areas, but I have also been given recognition for my accomplishments and more authority to grow my team. 

While start-ups and large companies are inherently very different, my experience in the two working environments provided me with a great set of learnings, experiences, and challenges I learned from and was able to overcome.