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
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
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.
Lindsey Osburn, Preschool Program Director
I am a dedicated early childhood educator with over a decade of experience, who thrives on making meaningful connections with children and their families. With an Associate’s degree in Early Childhood Education and credentials in Leadership, Program Development, and Administration from UW-Platteville, I have spent 11 years in the field, 10 of which have been devoted to one center before it sadly had to close. My passion lies in being a support for the young minds we care for and their families, guiding them through every journey they undertake. At home, I cherish my role as a wife to my husband, Rob, celebrating a decade of marriage, and a devoted mother to our two children, Braxton, 8 and Waverly, 5. Outside of my professional life, I enjoy expressing her creativity through drawing, coloring, painting and other creative outlets. However, the true heartbeat of the Osburn household is our shared love for baseball, GO CARDINALS!
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.
Nutrition Program
Lexi Treasure, Nutrition Coordinator
I went to UW Steven’s Point with a degree in Sustainable Food and Nutrition, so a nutritionist with a save the planet emphasis :). in my free time i like to read and play video games or wander the woods with my dog, Rebel. I love my dog so much. he’s a red heeler (like bingo!) and he keeps me active every day.
Ally Phillips, Assistant Nutrition Coordinator
Enrollment
Evelyn Villa, School Age Enrollment Coordinator
Erica May, Child Care Enrollment Coordinator
I have been working with Red Caboose for almost two years now, beginning as a Camp Caboose Comet Captain (how’s that for alliteration?) and recently, the Enrollment Coordinator for the childcare center (at the front desk, come say hi)! . My favorite activities to do during afterschool at Marquette are crafts, particularly anything involving a hot glue gun and rhinestones. I graduated from UW-Madison in 2024 with a degree in Sociology and Ed. Policy. Outside of Red Caboose, I love to read, watch reality tv shows, bike, and downhill ski. I am so excited to continue to work with the wonderful families of Red Caboose!
