If you're a manager in a startup (or want to be one), read this:

If you're a manager in a startup (or want to be one), read this:

Five lessons I learned as a manager in a massively fast-growing startup.

I left Google to join a 10-person startup.

Four years ago, I almost left Google for another startup, but I chickened out. I’d just turned 32. I had been at Google for almost 7 years. Doing something so new scared the jeebus out of me.

Then I heard about a different opportunity with a startup in real estate. I’m a real estate gal. Years ago my parents tried to sell their home and couldn’t. All the anxiety and sadness of feeling like they were chained to one place came hurtling back to me. I felt a strong desire to be part of their mission. So I jumped at the opportunity to be their first designer.

During the next 3.5 years, we built our first product, launched it, iterated, started operations in one market, launched various marketing campaigns, saw the company grow from 10 to over 400 people, raised a ton of money, and expanded into other cities. The company grew at an incredible speed and we were hiring at a rate that I could never have imagined. This naturally led me and some of the other early employees to grow into more leadership and managerial roles.

In just one year, my design team doubled in size.

And I had no idea what I was getting into.

Here are some lessons I learned from being a manager in a hyper-growth startup.

#1 — For every person that I added to the team, the relationships that I was managing grew exponentially.

As the company grew, we added more roles and product areas, which made the organizational structure increasingly complex and intertwined. Since our team supported almost every function in the company, we were feeling all kinds of growing pains. For example, if the marketing team needed new campaigns, we were the ones who designed their collaterals and advertising. What used to be one product split itself into multiple product areas, and each area needed designers to define their product flows and interfaces. The operations team needed X, the local markets needed Y. 

And the roles and responsibilities of people in each of these teams overlapped. It was getting harder for us to track where one team’s responsibility started and ended, and in a matter of weeks/months these dynamics changed all over again. A decision that once could have been made by a quick conversation in the kitchen now required several large meetings with different stakeholders from all sorts of functional areas.

For every new member that I added to my team, the relationships I managed grew exponentially. I wasn’t only managing the relationships between my team members, but also those between my team and the CEO, my team and their diverse business partners, and of course, my team and myself. Which brings me to another lesson:

#2 — I learned that conflicts were often unavoidable between people who had very different personalities and working styles.

A new designer joined my team. One of the first projects I assigned to her was working with a business partner on presentation decks. What I didn’t know was that this new hire valued taking her time to weigh all the options, reflecting extensively in order to make a thoughtful decision. On the other hand, the business partner expected tasks to be completed as soon as possible, including late at night and early in the morning. He didn’t care as much about quality but wanted to get things done quickly. As a result, the designer felt rushed to get things done on schedule. The conflict could not be resolved. I ended up moving the new hire off that project, but this first impression nearly destroyed her reputation in the company.

In a growing company, people with different working and communication styles were suddenly expected to work together. Collisions between employees were frequent and occurred almost every week. New hires found these collisions to be almost unavoidable in their first 2–3 months because they were still figuring out how they were expected to function in the team. I learned that setting up a new hire on the right team and the right project from the beginning was absolutely crucial.

#3 — I had to let go of what I thought my job was and learn new skills fast—like super fast.

With all of the responsibilities that came with being a manager, I was trained for none of them. I was no longer designing products. I gradually gave away my old job to my team so I could free up time to do more recruiting and networking, and attend meetings.

Most days, my calendar was filled with meetings and one-on-ones. I was absorbing so much information that I rarely felt bored. But there were times that I felt restless. There weren’t any exciting product problems to solve. I had nothing concrete to show at the end of the day. There were many parts of my job I enjoyed, but as someone who gets excited about building and creating things, I found this particularly challenging.

As a manager, I had to accept the fact that my day to day responsibilities was in a constant state of flux. I was no longer using the skills that I was trained for, skills I’d worked hard to acquire and loved to use. My job now required a whole new set of skills, not to mention engaging parts of my brain that I had seldom put to use in the past. I learned to trust my team to make their projects their own, and to execute those projects to the best of their abilities.

#4 — I realized that some employees weren’t able to grow at the same rate as the company.

I’ve always been a strong believer that people could grow into roles if they are given the time and opportunity to do so. What I learned was that not everyone could grow at the same rate as the company.

When the team was smaller, we had a certain rockstar employee. Then the company tripled in size in two years. Every employee suddenly had to deal with more relationships than ever before. It required people to assess the scope of incoming tasks, prioritize workload (sometimes ruthlessly), and communicate clearly with business partners. It required them to understand what the most pressing business needs were and spend the day working accordingly—or at least learn to communicate with their managers to get appropriate guidance. This rockstar employee’s new role required a completely different competence after one year. He couldn’t acquire these new skills fast enough to keep up with the company’s needs. Feeling loyal to him, I was in denial for months—only to realize that ultimately the best outcome was for us to part ways.

#5 — I learned that soft skills are essential to survive in a rapidly growing company.

When the team was smaller, I didn’t screen candidates for their soft skills. I couldn't care less about soft skills as long as they passed my bar of “not crazy.” I needed people to help build stuff right away. I needed talented people with great design skills. I thought that was all there was to it.

Then the company grew. The amount of actual work didn’t change because more people were added to the team and work was getting distributed equally. What changed was the amount of information that was miscommunicated and misinterpreted. The number of conflicts between people skyrocketed. In this growing startup environment, I noticed that those with high self-awareness and excellent communication skills not only adapted, they thrived. People loved working with them. They were involved in notably fewer conflicts. So they were given more opportunities. And their roles and responsibilities grew tremendously because they listened to feedback. I can’t stress this enough: soft skills matter as much as hard skills, especially in a startup environment.




In sum… my first few years as a manager in a growing company were rewarding because I learned a ton. But they were hard, too. I hired too fast without the faintest idea about possible repercussions. I made plenty of mistakes. I made bad hires. I had to fire two employees over the course of a year and a half, and I realized that firing people was the hardest thing I'd ever done. I learned to let go of ownership on projects that I helped create, and I learned a whole new set of skills. And finally, I figured out that having the right people on my team was more important than anything else.

I recently met a few other startup managers over drinks and discovered that their experiences were remarkably similar to mine. We bonded right away. We had all fought the same battles. We all suffered through anxiety, insecurity, and insomnia, but we all came out the other side feeling stronger and more resilient. Being a manager for the first time in a startup is like going through puberty. It's kinda awkward, it's kinda painful, and I was in a bad mood a lot of the time, but looking back, I realized those were some of the most interesting, ass-kicking years of my career.

Mary L.

Director of Product using AI to scale and accelerate growth (Former Shopify, Meta, Dropbox)

2mo

Just seeing this article, and it’s truly timeless! Love your personal anecdotes, especially about unavoidable conflicts and learning *super* fast. What a journey you’ve had from big tech to startup.

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Koji Pereira 🔥

🌱 Chief Design Officer at Neon (Ex: Google, Lyft, Twitter)

3y

Great article Jessica, your voice is visible in these lines. Glad you shared this with many people who may experiencing similar challenges or aspiring to be in a managerial role. It's definitely a totally different role, and many just jump into too quickly without realizing.

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Solid article Jessica. Great advice for anyone jumping from "the known" to the unknown of a startup environment.

Aimee Simpson

Senior HR Leader | HR Director | Chief of HR | Culture Champion | Lover of Innovation and Tech

5y

Fantastic article and so true in the startup environment.

Heqing Huang

Software Engineer at Apple

5y

Such a great article.

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