Emily Silberstein’s Non-Traditional Journey to Tech Leadership

Emily Silberstein, Senior Director of Product at Instacart, possesses a remarkable career trajectory driven by a unique blend of passion and purpose. 

Emily’s journey defies conventional tech paths, rooted in her passion for how systems could better empower underserved populations. She has set herself apart through her unwavering focus on product development that truly makes a difference, and her dedication to nurturing the growth of her team members. Her leadership shines through in her ability to turn ideas into real-world solutions, from minor user enhancements, to groundbreaking innovations. Ultimately, Emily’s story illustrates the power of adaptability and the pursuit of meaningful impact, both professionally and personally.

We asked Emily about how her career background led her to where she is today, how she’s grown as a leader since starting in her role, and the advice she would give to someone starting out on the journey she is currently on.

Q: Tell us about your career background. How has it led you to where you are today?

A: I have a non-traditional background for working in technology. I studied liberal arts and economic development, with a passion for how our systems could better empower underserved populations. My first job was working in venture philanthropy in Boston, identifying high-impact small nonprofits, providing them coaching and connecting them to financial support to fuel their impact. Learning how business principles could drive social change inspired me to get my MBA.

During business school at Harvard, I focused on social enterprise and worked on a business plan competition for a startup focused on using non-traditional data and machine learning to enable banks to lend to underserved small businesses and consumers in emerging markets, where information on credit risk through credit bureaus was sparse. I worked full time for the startup after graduation on the founding executive team, running our Asia business. This granted me the incredible experience of living in India and getting to work in places like Indonesia, Pakistan, and Peru.  

I joined the startup due to my passion about financial inclusion and unwittingly became a technologist with expertise in fintech and machine learning. This led me to Silicon Valley where I’ve had the opportunity to lead a number of different product organizations focused on advancing financial empowerment and productivity for small businesses and consumers. I currently work at Instacart, where I lead our product teams focused on making it the best platform for gig workers to make a flexible earning and our teams focused on keeping our platform safe and supportive when anything goes wrong. 

Q: What’s the most impactful career experience you’ve ever had? How does it impact your work to date?

A: After business school, I got a one-way ticket to India to see if I could build our startup’s business in Asia. From day one, things that might have sounded simple were complex—like figuring out how to get a SIM card or getting a tax ID to operate. It was humbling to be starting from scratch, having to cold call to sell a product that our customers, old-school banks, doubted, or having to challenge basic assumptions of the product; like that we could depend on reliable internet. It was very rewarding to see the product get traction and eventually help tens of thousands of people get loans who wouldn’t otherwise be able to. 

This taught me how to be comfortable in unknown situations and make relationships with people who can help you navigate and get up the learning curve. I learned how to ask a lot of questions and not make assumptions since I realized my prior experience might not apply. This has made me a more open-minded and creative leader.

Q: How did you land your current job?

A: I had worked with some amazing leaders at my previous company, and one let me know when a role opened up at Instacart. It was a perfect fit for my interests in helping use technology to provide financial empowerment and a great time in the company's trajectory during the pandemic to join. 

Q: What is the most rewarding part about your current role?

A: There are two things that get me up every morning. 

First, shipping products that make a difference in people’s lives. At times, that can be small improvements to things that annoy users. Other times, it can be disruptive products that enable us to delight in ways they couldn’t have imagined. It’s a long process to take a product from an idea to the hands of users, but when you get positive feedback it makes all the difference.  

Second, helping those around me grow and do the best work of their lives. I love the opportunity to support my team and help stretch them with new challenges. My team’s success is my success. I’m constantly amazed at how good people rise to the occasion and do really hard things. I get a lot of meaning from anything I can do to help them along that growth journey. 

Q: What does your current day-to-day look like?

A: I usually spend the first hour of the day catching up on emails, Slacks, and reading/giving feedback on any documents that have been sent. We are largely remote, so I spend the majority of my day on video conferences. My favorite part is typically one-on-ones with my team or manager, where we are brainstorming ideas and talking through hard problems. I spend a good part of the rest of the day having team meetings, cross-functional reviews of product proposals, team check-ins, and interviews. It’s easy for my day to unintentionally get filled with back-to-back meetings all day, but I try to keep 20 percent open since something time sensitive usually comes up. Since we are a fast-moving business, I like having some flex space to have the ability to respond to what is important.  

Q: How have you grown as a leader since you started this role?

A: I started at this job during the heart of the pandemic and we continue to work remotely. Working through Covid-19 and the remote environment has required me to be a much more deliberate leader. 

Covid-19 meant understanding different people's experience working from home, ranging from the challenge of child care, to feelings of isolation, to getting a quiet space to work. This meant finding ways to give people flexibility and create an open culture where they felt they could express what they needed.

Starting a new job during this time was also a challenge in relationship-building. I had to spend extra time one-on-one with people to make up for the casual conversations that would have happened in the office. 

I had to learn how to adapt my communication skills, which often meant knowing when to pick up the phone to avoid long Slack conversations or finding more formal ways for teams to stay up to date on what is happening through regular newsletters and all hands. 

We get the team together periodically and have found that really investing in spending time together to get immersed in our customers' needs, get invested in the next big opportunities, and build the team culture pays dividends.

Q: What’s something you do outside of work that makes you a better leader?

A: I read a lot of fiction, or, more specifically, you’ll find me listening to audiobooks in my downtime like when I’m doing laundry or running errands. When I was younger, I thought I should only read nonfiction in order to maximize my learning. However, I’ve found that I learn a ton in fiction too, and because it's so engrossing, I power through a fiction book in a day or two. 

I typically like reading historical fiction or fiction about another place/culture. These books help me gain new perspectives, like how a king hundreds of years ago handled a gnarly decision for battle or how a couple worked out a seemingly irreconcilable cultural difference. This gets me outside my bubble and sparks me to think of totally different ways of operating. 

I also find that work can take over my thoughts and I can get wound up, and I'm a more effective leader if I can keep it in perspective. Having an outlet of reading helps me engage my mind to something totally different, so that when I get back to thinking about work, I have some more distance and perspective. 

Q: What advice would you give someone starting out on the journey you’re on?

A: Expect your path to be windy. Early in your career, you may think you know exactly where you want to go and the very specific jobs you need to get there. Both roles and you will change, so instead focus on what you can get from each role. 

Get as many reps at leadership and taking initiative as possible. Only an intern? No problem—how about starting a weekly lunch with all the interns to review industry news? New to a company? Why not offer to collect all the documents and resources from your first few months to create a tool for the next new hire? Leadership opportunities rarely look like a senior leader singling you out to pick you to be in charge of a sexy, high-profile project. Instead, find ways to be proactive in making your organization better. Stepping up to take on leadership in making your organization better will give you tons of skills to enable you to grow, ingratiate yourself with the organization, and get reps as a leader.

Emily is a member of Dreamers & Doers, an award-winning community that amplifies extraordinary women entrepreneurs, investors, and leaders by securing PR opportunities, forging authentic connections, and curating high-impact resources. Learn more about Dreamers & Doers and get involved here.

The views and opinions expressed herein are the views and opinions of the author and do not necessarily reflect those of Nasdaq, Inc.

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