Meet Our Team

Board of Directors

Blake Roberts Crall, Board President

I have been part of the Red Caboose community since 2021, when my family moved to Madison, and my two kids enrolled in the preschool program. I am originally from California and grew up bouncing around overseas, and am honored to now call Madison home and to be raising my kids here. Early education and childcare is the backbone of our society, and I am proud to be part of Red Caboose, which is a leader in this field. In my professional life, I am the Program Manager for the Madison Forward Fund, the city’s guaranteed income pilot. My work has mostly focused on economic justice and social welfare policies. In my free time I love reading fantasy and sci-fi books, doing pottery, and being a goofball with my kids.

Phil O’Leary, Board Treasurer

I currently operate my family farm in Rock County Wisconsin and am an emeritus University of Wisconsin-Madison engineering professor. I am an agricultural and environmental engineer. As Engineering Professional Development chair, I coordinated outreach programs across a wide range of engineering disciplines. I also created and directed, the Camp Badger Engineering Summer Program, a large middle school experiential learning initiative.

Chris Sewell, Vice President

Generic Headshot Female

Audrey Conn, Board Member

KC Gilbertson, Staff Liaison to the Board

I have a social work degree and have been working with children and families for many years including as a Site Supervisor and Camp Director with Red Caboose since 2008.

Cheryl Heiman, Staff Liaison to the Board

I have been a teacher with Red Caboose since 1974 and have been the Lead Teacher in the Turtle Room for most of those years. Things have changed over the years, but our commitment to providing exceptional care and early childhood education continues.

Becky Mather, Board Member

Scott Coleman, Board Member

Generic Headshot Female

Leadership Team

Lisa Fiala, Executive Director

I have been with Red Caboose for nearly 18 in various roles including School Age Program Director, and Project Administrator. Now I’m back in the role of Executive Director. I am passionate about high-quality care and education for all of the children in our community which creates a diverse, inclusive environment!

Wendy Rakower, Director Emeritus

I served as the Executive Director at Red Caboose for many years. I am grateful to continue to support Red Caboose’s development efforts.

Ashlee Causey, Preschool Program Director

I’m excited to join the Red Caboose Family! I’ve worked in Early Childhood Education for the past 11 years as a teacher. I’m originally from Southern California and received my Bachelor of Science in Child Development from Fresno State. I’ve always been passionate about working with children, families, and colleagues who share that same passion. I believe to create a safe and fun space for children to flourish, staff must feel the same! This is the environment I hope to cultivate with all of you!

Robby Schiller, School-Age Program Director

Administrative Team

Jennifer Roughen, Billing Coordinator

Joining the administrative team at Red Caboose is an opportunity to combine my accounting experience and my child care experience. I am also utilizing my childcare nutrition experience to support our Nutrition Program. I am looking forward to working with and supporting all of our Red Caboose families.