Taking the Leap: 6 Lessons in Making the Most out of Career Transitions

By Kat Rumbles on November 2, 2018

College to first job. Academia to startup. Large corporation to startup. Whether deciding which job offer to take coming out of school or looking for your next career move, there are seemingly endless factors and potential outcomes to consider when evaluating new career opportunities. Career transitions are rarely simple, and they can be even more complex and challenging for women moving across male-dominated industries.

To help understand how to make the most of (and ace) these transitions, our team hosted a panel with three of our portfolio companies at Grace Hopper Celebration, the world’s largest gathering of women technologists. Ann Ruble, an Operating Partner on our team at Two Sigma Ventures and a Managing Director at Two Sigma, sat down with with Raquel Ledezma-Haight of x.ai, Maureen Teyssier of Enigma Technologies, and Renee Orser of NS1 to cover everything from your first job to negotiating a new salary.

1. On Taking the First, Unknown Step

How many of you knew what you wanted to do post-graduation before you came to college? As an exercise in understanding our career trajectories, Ann Ruble kicked off the session by asking the entire room that question. Not a single person raised their hand, showing how career paths are often nonlinear with unexpected beginnings and endings.

Raquel came to school wanting to do neuroscience research, interned in marketing, finance, and as a lab assistant. She’s now a Product Manager at x.ai. Maureen planned to major in English and Chemistry and ended up completing a PhD in Computational Astrophysics. After exploring a career in academia, she decided to join a startup and is now a Technical Lead and Manager at Enigma Technologies. Renee studied International Relations and Arabic. She worked at Americorps and as a consultant before becoming the VP of Engineering at NS1.

It was only by building experience and tenacity — through part-time jobs, coffee chats, different internships, past jobs, boot camps — that they were able to land where they are now. This experimentation, which can sometimes feel like a detour, was critical in each of their career journeys and was necessary to get them where they are today. Ask questions, be curious, learn from those around you. Don’t be afraid to take a risk and try something new. Until you try it, you’ll never know if a new role or skill might end up being a perfect fit.

2. Prioritizing Your “Must-Haves”

What’s most important to you in a role and at a company? We all have unique wants and needs at work, from wanting lateral or upward mobility, to a more flexible work schedule, or the opportunity to work on a variety of projects. If you are finding that your needs aren’t being met, Maureen advises writing down what you don’t like about your current role or company. Once you have your list, look through each one and determine whether or not the solution is within your control. For example, is the company culture, the leadership team, or something else getting in the way of your success? If so, then it’s probably time to look for your next opportunity outside of the company. If you find that the things you’d like to change are ultimately within your control, it might be time to advocate a bit harder for yourself, ask to work on new projects, or take other steps towards achieving your goals.

3. Make Yourself Indispensable; Know your Worth and Negotiate

Take on responsibility. Work on teams that have different skill sets than you. Find the intersection between your career goals and what will benefit your company’s bottom line. After being at Enigma for about 6 months, Maureen realized she could take on more responsibility, which would also give her the career growth and managerial skills she was looking to develop. She approached her manager with an outline of a plan of shifting from a Senior Data Scientist to a Technical Lead and Manager, and he agreed to give it a try. From there, Maureen continued to receive more opportunities to grow as she succeeded in delivering more value back to the company.

She and the other panelists also advocated for making your work and your skill set an indispensable part of the team, so it’s difficult for the company to imagine what they would do if you left. Once you’ve become a crucial member of the team, ensure that your boss and your team know your value and take the time during performance reviews and 1:1s to negotiate for what you want and need. These discussions go best when you can align your professional goals with the company’s goals. Make your advancement a solution to the company’s challenges, rather than an additional problem the company has to solve.

4. Find a Mentor and Be a Mentor

All of our panelists stressed the importance of finding a network and mentor. Leverage your company’s network, but don’t be afraid to look elsewhere for valuable career advice. Renee suggested reaching out to a well-connected contact and asking for introductions to others who might have been through a similar challenge. Raquel also stressed the importance of leaning on others:

“In the tech and startup world, so many of our roles are really new and haven’t existed, so I find myself leaning on peers and people just above me.”

It’s not always the most beneficial to depend on the most senior leaders; rather than getting advice from people who completed the same problem 10 years ago, someone who just dug themselves out of the trenches yesterday may prove to be more helpful. Then, pay it forward: go, talk, volunteer, and become a mentor for someone else. You know how nerve wracking it can be to send that cold email, so when you get one, take a minute to answer.

5. Build a Toolbox of Skills and Bring It Wherever You Go

If you’re an engineer, it’s important to continue defining your technical skills, but also spend time sharpening soft skills. If you’ve cultivated your soft skills, then work on building a new skill set to add to your toolbox. When Renee was moving between industries, she wanted prospective employers to understand why her previous work at Americorps and in consulting was relevant for the roles she was applying for in the tech industry. To make this clear, she added a section to her resume called ‘People Skills and Programmatic Skills,’ which included programming languages as well as facilitation and program management so potential employers would make the connection.

6. Finally, enjoy the journey

In her closing remarks, Maureen shared a piece of advice she wished she could give to her former self: stop, sit down, and enjoy the company of others with no formal strategy of negotiating or networking. This is how you build real relationships; it will bring joy to your work and to your life. Finally, and perhaps most importantly, take time to reflect on what you’ve learned from each experience, including the steps in your career that felt like setbacks at the time. Relish in the lessons that happened between, and inevitably, you’ll continue learning and growing as you consider your next career transition.

Enigma Technologies is an operational data management and intelligence company. NS1 is an intelligent domain name system (DNS) and traffic-management platform that uses a data-driven architecture to make routing decisions in real-time. X.ai is an artificial-intelligence-driven personal assistant that combines machine learning and human intelligence to schedule meetings.

The views expressed herein are solely the views of the author(s), are as of the date they were originally posted, and are not necessarily the views of Two Sigma Ventures, LP or any of its affiliates. They are not intended to provide, and should not be relied upon for, investment advice.