Issue #46: Career Lessons From 15 Years in Tech

Recently I posted a list of lessons I’ve learned from 15 years and 5 companies in the tech startup scene in New York. I’ll share my list and then narrow in on the stories behind some of these lessons.

1. You have to ask for what you want
2. “No” just means “not right now”
3. Say “yes” to new opportunities that are presented to you—especially when you are not sure if you can do it
4. Dedicate yourself to mastering a craft
5. Don’t be afraid to take a step back to take 2 steps forward
6. Don’t compromise your values for a job or company—it is never worth it
7. Understand what your manager’s boss needs and help yours achieve their goals
8. Regardless of your role, focus on identifying and solving the most important problems in the business
9. Seek out "mentorship moments" from everyone around you—you don't need a formal mentor and can learn from anyone
10. Your company does not care about you—the people at the company often do care about you—but at the end of the day it is a business and the company will make choices in the best interest of the company
11. You are the only one who can take control of your career and move it forward—don’t expect others to do this for you

Don’t be afraid to take a step back to take two steps forward

I learned this lesson early in my career. I'd spent almost seven years in an educational technology company called eChalk as an account manager. For that entire time my role was consistent which allowed me to master the craft of account management. 

At the time, I felt that I had achieved a level of seniority, so when I began a job search, I was looking for either a team lead or management position, or a very senior-level account management role. 

But then I saw a Customer Support Agent opening at Zocdoc, and I had an instinctual feeling that this opportunity would lead to something better. One caveat—the salary was less than half of what I was making before. Objectively, this was a step back in my career, especially at a time when I wanted to take a big step forward. But I spent the next nine months on the phones proving myself, and eventually earned a chance to design a business case for building out a post-sale function that didn't exist at the time. 

Although I originally took a step back, I ended my time at Zocdoc as a manager who grew the team from 0 to 25 people over 18 months. It was my first opportunity to hire a team, create processes, and collaborate with other departments. I learned a lot in that short time frame, and my rapid growth only validated my decision to take what others considered a demotion. 

The truth is, especially when you’re earlier in your career, compensation and role matter a lot less than you’d think. What matters is the opportunity to grow fast in terms of responsibilities and exposure; and if you stay too long at a place where you’re comfortable, you’re missing out on future growth.

Find gaps in the business and then solve them, regardless of your role

Eventually, I was hired as the head of account management at Managed by Q. I immediately noticed that the business was operationally heavy. There was a long list of tasks most new managers would have focused on in their first 90 days but I could see the most pressing issue for the business was the operations problem. Solving this would grow revenue for the company and deliver great customer outcomes. 

There were plenty of people who knew about this problem—but I raised my hand. I called it out, aligned with the CEO on its importance, invited the right individuals to the table, and shepherded the team towards a solution.  While some thought it was “out of turn” as my first project, I just got to work. And in time, the result was a positive impact on revenue, customer experience, and employee satisfaction. 

I learned that no matter the role I’m in, I’ll always pick my head up and look around, scanning for gaps that need to be filled or areas I can lend a hand. I firmly believe this practice opened the door for me to take on more responsibility. After only a year and a half at Managed by Q, I was promoted to COO.

To progress, you have to take control of your career

Earlier in my career, I thought it was my manager’s job to carve out a path for me, give me clear expectations of how to be promoted, and support me along the way. In reality, that's not how it works. You need to be in the driver’s seat of your career. 

One great way to start taking control is to document the outcomes you create. Results that seem small in the moment are compounded with time. For example, if I helped increase the win rate of service requests from 10% to 20% over a three-month period, I’d translate that into a revenue number, so I could track my impact. If your goal is a promotion, track how you’ve tactically helped the company over time.

Achievement for achievement's sake is unsatisfying

I always had a strong desire to get promoted to the C-suite. But once I got there, it didn’t feel as good as I thought it would. I realized that doing what actually matters to me in my work is truly satisfying. 

Sometimes you’ll get on a track towards a high prestige role that doesn’t energize you. Don’t chase it. Learn about how you personally want to spend your time, taking two steps back if necessary, so you can progress in a way that’s fulfilling. 

My goal now is to be a positive impact and help people succeed professionally and personally, whether it’s a customer, teammate, or friend. My career is more than achieving a title or earning a certain amount of money—it’s about being the lever of support I wish I had earlier in my career. 

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