CalendarFly is a single source scheduling solution for families, with the activities and assignments of children and parents updated instantly and automatically. By creating a superior and free scheduling option for schools, CalendarFly has created an easy-to-use and free collaborative calendar that is perfect for families. Students’ personal calendars are updated with school and sports events and assignments instantly and automatically and parents’ personal calendars are updated with this information and their own. And, because CalendarFly is free, all school communities, regardless of income, can use it. Family scheduling and tracking is made simple – for everyone!

CalendarFly hopes to improve education outcomes by supporting a collaboration between schools and families and the engagement of parents in their children’s school lives. CalendarFly has gone live in two low-income districts in New York this spring and is seeking funding for a mass roll-out in 2010.

Business Model: CalendarFly employs progressive pricing and segmented advertising. Marketed as a free service for low-income school districts, CalendarFy will profit from premium services (like BlackBerry integration) to more affluent districts and end users. Calendarfly will also support its free services through targeted advertising served to adult users.

Founder: Before founding CalendarFly, Drew worked on Wall Street, evaluating derivatives and structured finance products, and as a marketing and business development for an online financial firm. He has partnered with Jason Cernansky, whose background includes technology development for governmental agencies.