Welcome to Leader’s Day 2024.

Meet with experienced leaders who can encourage and assist as you guide our movement forward. Come together to advise and pray for one another.

Join us online for a selected Leader’s Day track.


Liz and Wally Caddow

Liz and Wally Caddow

Liz Caddow founded Trinity Classical Academy in 2001 in Santa Clarita, CA with her husband, Wally Caddow. Today Trinity is in its 23rd year with 560 students in grades TK – 12th and has graduated 13 classes totaling over 400 students who have attended some of the...

Kyle Maestri

Kyle Maestri

Kyle Maestri is a passionate follower of Jesus Christ. He grew up in a Christian home where he was taught to ask hard questions which deepened his faith at a young age. He attended Biola University and was part of their first full graduating class of the Torrey Honors...

Lindsey Burke

Lindsey Burke

As Director of the Center for Education Policy at The Heritage Foundation, Lindsey Burke oversees Heritage’s research and policy on issues pertaining to preschool, K-12, and higher education reform. Burke’s research has been presented at academic conferences and...

Mark Koscak

Mark Koscak

Mark Koscak has served as the Director of Development at Providence Academy in Johnson City, TN, for 21 years. He also consults domestically and Internationally for Holland Educational Consulting. Mark and his bride, Beth, have been married for 30 years. They have two...

Andy Shapleigh

Andy Shapleigh

Andy Shapleigh grew up in St. Louis, Missouri and attended the University of Kansas, earning a liberal arts degree before moving to Tulsa, initially in sales and later in a mar- keting and fund-raising position for a non-profit organization. After nine years in a cor-...

Tracy Robinson

Tracy Robinson

Tracy Robinson lives in Hickory, NC with his wife, Gayle. The Robinsons have six children, five of whom graduated from Hickory Christian Academy, with the youngest recently completing his senior year at HCA in 2024. Tracy grew up in a Christian home, became a believer...

Keith Phillips

Keith Phillips

Keith Phillips is Head of School at Schaeffer Academy in Rochester, Minnesota, where he has served for the past 26 years. Prior to Schaeffer Academy, Keith served as an administrator at Kauai Christian Academy on the beautiful north shore of Kauai and received an M....

Ty Fischer

Ty Fischer

Ty Fischer has been the Head of School at Veritas Academy in Leola since 1997. He received a BA in history from Grove City College and a Master of Divinity from Reformed Theological Seminary in Jackson, Mississippi. He has also studied at Cambridge University at the...

Danielle Dillenschneider

Danielle Dillenschneider

Danielle Dillenschneider has taught at Bayshore Christian School for nine years. In her time at Bayshore, she has taught literature, rhetoric, debate, writing, and art history, and she has taught 7th through 12th grade students. She has also earned a Master’s in...

James Cowart

James Cowart

James Cowart serves as headmaster at Trinitas Christian School in Pensacola, Florida. Before coming to Trinitas, he was headmaster at Paideia Academy in Knoxville, TN, from 2009 through 2014. James and his wife Joy have five children all of whom attend Trinitas:...

David Seibel

David Seibel

David Seibel, as the head of school, aims to cultivate a generation of scholar-disciples who are passionate about learning. Husband to Brooke and father of two current and an additional two future Coram Deo Academy students, David holds a doctorate of education from...

Dr. Brad Dolloff

Dr. Brad Dolloff

Dr. Brad Dolloff has been the dean of the Lab School at School of the Ozarks, a classical Christian K-12 laboratory school of College of the Ozarks, since its opening in 2012. Before accepting the position as the headmaster here, Dr. Dolloff served as a mathematics...

Dr. Benjamin Merkle

Dr. Benjamin Merkle

Dr. Ben Merkle is the president of New Saint Andrews College, as well as a Senior Fellow of Theology. He holds a DPhil in Oriental Studies and an MSt in Jewish Studies from Oxford University, England; an MA degree in English Literature, a Greyfriars Letter, and a BS...

Tim Dernlan

Tim Dernlan

Dr. Timothy Dernlan earned an Ed.D. in Organizational Leadership from Ashland University and was named the Outstanding Graduate in 2013. He also holds an M.Ed. in Educational Leadership from Lehigh and a B.A. in Communication and Education from Purdue. He currently...

Brad Layland

Brad Layland

Brad Layland, CEO of The Focus Group, first learned how to raise money as a college student in 1993, while seeking to raise personal support as a part-time staff member for Young Life. Over the course of 20 years at Young Life, he developed his passion for and...

David Goodwin

David Goodwin

David Goodwin has served as the president of the Association of Classical Christian Schools (ACCS) since 2015. Formerly, he was the head of The Ambrose School, a classical Christian school in Boise, ID, from 2003 through 2014. During this time he oversaw the design...

LEADER’S DAY AT A GLANCE
Grand Ballroom 1, 2, 3 & 4
8:00–8:30
Coffee
8:30–8:45
Welcome
8:45-9:30
Plenary — Leading in Ambiguity and Conflict – Ben Merkle
9:45-10:30
Workshops
Panel Discussion — Board Members: Building Long-term Head of School Leadership – Fischer, Phillips, Robinson & Shapleigh
The Conflict-Free School: Why You Cannot Have One and What to Do About It – Dernlan & Seibel
10:45–11:30
Workshops
Creating an Agile, Relevant Strategic Plan for Your School – Brad Layland
How Aligned and Practiced Values Benefit School Culture – Danielle Dillenschneider
11:30-1:00
Lunch (on your own)
1:00-1:50
Plenary — The “Year” of School Choice Continues – Lindsey Burke
2:00–2:50
Workshops
School Choice Funding—Blessing or Curse? – Cowart & Maestri
Identifying and Training New Board Members – Tim Dernlan
3:00-3:50
Workshops
Panel Discussion — Heads of School: ’This Isn’t Easy–Help Anyone? – Fischer, Phillips, Robinson & Shapleigh
Ready, Aim, FIRE! Defining, Refining and Announcing Vision – Mark Koscak
4:00-4:50
Workshops
We Started a School and Surprise—It Worked! – Liz and Wally Caddow
Is There Really a Classical Difference? – Brad Dolloff
4:50-5:30
Regional Gatherings for Prayer

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