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Sean Casey

Head of Product for divvyDOSE


Sean Casey is an experienced entrepreneur, technology executive, board member, and adviser. He is currently the Head of Product for divvyDOSE, an early-stage tech-enabled pharmacy, where he brings his technology and leadership skills to help scale the business. Sean’s life as an entrepreneur started in high school when he launched a web site for the local music scene in Chicago. In 2001 Sean went on to attend University of Illinois at Chicago for Computer Engineering and in his freshman year co-founded All Information Services (AIS), a boot-strapped technology consulting company serving small businesses. After 10 years of growing AIS Sean co-founded Shiftgig, a labor marketplace with over $50MM in venture backing. He served as CTO at Shiftgig and was responsible for building a team and defining the direction of the tech platform and product road map. Sean left Shiftgig in 2017 to pursue a life long desire to live in a new city and to get involved in early stage startups again. Over the years he and his companies have earned various awards and recognition but he’s most proud of the positive impact his companies have made on people’s lives.

Sean recently relocated to Nashville with his wife and two golden retrievers.


Q. What excites you most about the Wond’ry?

A. Being able to offer guidance and share my experiences with entrepreneurs at the very beginning of their journey. I am eager to help them avoid mistakes a lot of entrepreneurs make.

Q. What do you feel are the most important skills you have to offer in your role as a mentor?

A. The diverse experiences I’ve had, the broad set of roles I’ve held, and my ability to listen and understand problems fully.

Q. What has been your proudest moment in your career?

A. I didn’t realize it at the time but it was hiring someone for the first time at my first company. It meant we were growing and in a position to afford bringing on help. It also meant giving that person an opportunity to shape their career.

Q. What has surprised you most about your job?

A. How candid other successful people have been about their struggles. It taught me to be more open and to share my failures as openly as my successes. Failure is easy to repeat, success is not.

Q. If you could do everything over again, would you make the same career choices?

A. Absolutely. Every step has been a learning experience and without the minor stumbles along the way I wouldn’t be as strong of a person.

Q. In your opinion, what is the most important quality for success?

A. Humility. You need to be willing to accept advice, aware you don’t know everything there is to know in the world, and accept the fact that you will make mistakes. This helps you adapt to situations and make course corrections along the way.

Q. When you were a child, what did you want to be when you grew up?

A. An architect. I knew I wanted to build things but as the internet became more accessible that drive turned to building software and later building companies.

Office Hours:  By appointment only

Areas of Expertise: Finance, Fundraising, Leadership, Legal, Operations, Presentation, Product Design, Technology