Sarah Fishleder ’00 is the Founder and CEO of WayScout, a tool for falling in love with a city. While at Wellesley, Sarah studied Philosophy and participated on the Student Council to the Board of Trustees, Committee on Curriculum and Instruction, and Academic Review Board, in addition to spending a few early mornings rowing on the Charles. After graduating in 2000, Sarah worked in strategy consulting, city planning, and real estate development and analysis.
Please give a brief background on yourself and your career.
I graduated in 2000 with a degree in Philosophy. The summer before my senior year and throughout my senior year, I interned at Hill/Holliday, an advertising agency in Boston. The internet was exploding and people were just starting to understand how web and mobile technology would change the way we consume information and make purchasing decisions. This led directly to a strategy consulting job focused on the high tech and telecommunications sector. In this role, I developed strong financial modeling and business analysis skills. After moving to a new city, I transitioned jobs and started to apply these skills to analyzing cities and real estate at a planning consulting firm. Cities are multifaceted, and real estate development requires not only great design and engineering, but also a workable marketing plan and financing package. This is when everything clicked for me and was the start of my current path.
I founded WayScout to provide a new type of publishing platform that ties information to locations. I love walking around a new city to find out what makes it unique and vibrant. As a city planner and real estate consultant, I’ve worked with cities, non-profits, real estate developers, and other professionals. These groups know their neighborhoods, and they strive to highlight what is unique about their cities. They often don’t have large technical budgets or staff members who can develop an app at the drop of a hat. WayScout removes the technology barrier to creating and sharing location-oriented content. Individuals, blogger and traditional publishers can use the system, too. Our first products are rolling out now. We have a web-based guide creation platform that publishes directly to the iOS app. A guide could be a simple list of favorite dishes in a particular city, or it could be an immersive, media rich historical tour. As the platform grows, we will release a number of other tools for creating content. Coming from the perspective a city planner, I hope that WayScout’s products encourage people to explore their cities, and to share in a community dialogue about places. There is a whole world of content and context that is missing from our current experience of cities, but WayScout can change that.
Other aspects of my past: I managed a real estate analytics group at CitiMortgage during the height of the housing boom. It was a fun position and I got to work within a large sales oriented company, which I recommend to anyone. I also received a Masters of City and Regional Planning at the University of Pennsylvania, which allowed me to complete a Certificate of Real Estate Design and Development at the Wharton School. Someday, I want to return to my real estate roots and continuing investing and developing interesting projects. Also, I worked on the data warehouse and parking sensor build out of the SF Park program in San Francisco to demonstrate demand based pricing for parking.
How has your career changed since you originally envisioned it at Wellesley? What other careers did you consider as a student?
I had been politically active at a young age. I volunteered on my first political campaign at age 13 and worked nearly full-time on a campaign my senior year in high school. This meant that I spent college overcoming a narrative that I should run for office and go to law school. Each internship or career idea was in response to these expectations. Over the course of my time at Wellesley, I changed the way I looked at my skills and myself.
How has Wellesley contributed to your career?
Wellesley cemented in me a confidence that is unshakable. Life, work or personal, has its ups and downs. No matter where I am in that cycle, I have this place in my gut where I know who I am and what I can do. I can dust myself off and keep moving. Since starting WayScout, I’ve been judged and criticized in harsh ways that I didn’t expect. My passion for cities and my desire to change how we experience places will keep me going. My belief in my abilities is a constant touchstone for me, and that is a direct result of my time at Wellesley.
I always know that I have a home with Wellesley women. The Wellesley alumnae network is amazing. Wellesley women do so many interesting things! If you are curious about a topic, or need input on an idea, there are so many resources to be found within the community. Wellesley women are passionate and pursue full lives. I’ve met an alumna who lived in eight countries, and another alumna who is pursuing a side career in opera singing. The support of my Wellesley sisters has been very important to me. With WayScout, I’ve gotten to know many current students and young alums. I always have a smile on my face when I talk with the younger members of our community. I always feel truly heard and supported by the older members of our community.
Finally, Wellesley teaches its students to look at problems in a multifaceted way and to write well. These skills are very important in the workplace, and can set you apart from the pack. Looking at the big picture, but mastering the details has served me well throughout my career.
What is a typical work day or work week like for you?
In a typical work week, I talk to a lot of people. I talk with the software developer several times about bug fixes and new features. I work with the marketing and content interns on setting priorities and completing tasks. I do a lot of reading to keep up with competitors and other aspects of the tech industry. Since WayScout is bootstrapped, I spend time working on free or low cost marketing strategies. I look for opportunities to partner with other companies or groups, or I create content that can be used in a way to promote the company or inspire new relationships. Externally, there are two main groups with whom I regularly talk: Customers and supporters. On the customer side, I talk with both guide creators and guide users. Since we are launching with a two-sided marketplace of content, both groups are vital. I am actively recruiting content for the platform, which means finding interesting content and pitching ideas to community groups or bloggers. I have to educate them about WayScout and convince them to try it. I also talk with a lot of users to find out if the app is working for them and what new features or redesigns would improve their experience.
The supporters I talk with are a diverse bunch. They can be founders of other startups, friends, potential advisors, members of the community, or funders. These are people interested in WayScout and who have made the time to help in some way. The important role of this group plays cannot be overstated. These people provide insights, ideas, and help at almost every turn. Many of these people are people I’ve gotten to know since I founded WayScout. I see myself as more of an introvert, so I am especially proud of myself for creating and maintaining this group.
One aspect of my work day that is a constant is that I take a few minutes at the end of the day to plan the next day. I establish a set of priorities for the next day and refactor my week, so I can dive in a get to work each morning. When I started doing this 5 or 6 years ago, I was instantly more productive.
What piece of advice would you offer students looking to get into this industry?
Get started. If you want to create a company of your own or have an idea you want to pursue, it is a good idea to roll up your sleeves and get started. It is easy hold off and wait for the right time, or when X,Y, or Z has fallen into place. The truth is there are not perfect time and no perfect set of conditions. The experience of starting a company isn’t what you think it will be. There are unexpected aspects of what is ahead, so get started and see what happens.
What do you wish you had known as a student?
I wish I knew that the classes you take as an undergrad don’t matter as much as you think. I wish I had experimented more and taken art classes. Although I majored in Philosophy and loved it, I took a lot of classes that I thought would look good if I applied to law school later. That was silly.
If you could come back and take one class at Wellesley what would it be?
The Japanese painting course that I didn’t take in my final semester. I wish that I had taken art courses throughout my time at Wellesley, but I never did. This is my biggest regret.