1. Ian Cummings
Midland School • P.O. Box 8 • Los Olivos, CA 93441
(805) 691-4100 • ianmaccummings@gmail.com
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Experience
College Access Consultant Since June 2015
 Collaborating on a book guiding students to consider various paths to success after high school
without taking on crippling college debt. Draft nearing completion; samples available upon
request
 Founder of College Pathways, a non-profit college counseling service for low-to-moderate-income
students
United Way of Santa Barbara Summer 2015
Site Coordinator—Oversaw operation of the Santa Ynez site for Fun in the Sun, a summer
learning program for 48 low-income elementary and middle school students. Supervised five staff
members and two counselors-in-training.
Midland School, Los Olivos,CA 1987-1988, 1994-2014
 Academic Leadership
 Professional Development Coordinator—Led collective professional development activities of
the faculty; developed summer assignments for teachers; planned and led discussions and
exercises on course planning, evidence-based teaching practices, development of school-wide
principles of assessment, and implementation of appropriate homework loads; provided the
faculty reading assignments and written reflections regarding our progress. Wrote Midland-
specific statement of mission and philosophy for professional development, faculty survey on
assessment, and school-wide rubric for assessment; collected and organized two years of data
on Midland student homework loads in all classes. Helped steer school policy on academic
issues as a member of academic advisory committee and education committee of the board.
Served as site-based mentor for final stages of colleague’s credentialing process.
 Humanities department chair—Increased school’s graduation requirement for humanities
credits; developed department-wide rubric for writing assessment; initiated delineation of
grade-specific writing standards; worked with administration and teachers to develop mission-
appropriate admission standards, curriculum, and instruction for English learners.
 Curriculum development—Co-developer of thematic, interdisciplinary American Studies
curriculum that continues to be used after twelve years.
 Team teacher—Collaborated with four different colleagues—three of them new to the school
when collaboration began—in team-taught humanities courses.
 Administrative Leadership
 Board work—Served on strategic planning committee, head search committee, education
committee; wrote reports on day-student program and future of athletics program; wrote
portions of Midland’s statement of mission and philosophy.
 Athletic Director—For two years managed 15 programs and $20,000 budget; handled
scheduling, transportation, purchasing, record-keeping, and communication with entire school
regarding athletic programs.
 Chair, Student-Faculty Council—Worked closely with head of school on most major disciplinary
matters as well as policy issues.
 Hiring—Conducted the searches for one full-time English teacher and one part-time theater
director.

2.  Accreditation—Contributed to three self-studies for accreditation purposes, drafting portions of
each.
 Advising coordinator
 Recycling program manager
 Student Development
 Teacher— U.S. History, including Advanced Placement and honors classes; World History;
English; Acting; Spanish 1, 2, and 4; Senior Thesis.
 Varsity Coach—Sixteen seasons of boys’ soccer, eight of girls’ soccer, two of baseball, one of
boys’ volleyball.
 Student-Faculty Council—Ten years as chair, leading school prefects and class presidents
through debates on discipline and school policy, teaching rules of order, constitutional
principles, and ethics.
 Theater Director—Directed 18 productions, including Almost, Maine; A Midsummer Night’s
Dream; Wit; Twelve Angry Jurors; Little Women; and Our Country’s Good.
 Advisor—Two decades of parenting teenagers.
 Trip Leader—Two years as leader of junior class service-learning trip to the San Joaquin
Valley; co-led three wilderness backpacking trips of more than 40 miles each; assisted on
numerous other camping expeditions.
RelevantPreviousExperience
Educational Testing Service Summers 2003 & 2004
Read and assessed 800+ Advanced Placement U.S. History exams per session.
American School of Guatemala 1992
Taught 8th-12th graders English, U.S. History, and political science/economics at multinational,
bilingual school.
North Shore Suburban Education District, Highland Park, IL 1991
Assisted in high school classrooms for mentally handicapped students.
Times Tribune, Palo Alto, CA 1983-1987
Covered high school and youth sports for Palo Alto’s daily newspaper, including a brief stint as
a columnist. Also wrote for the Cardinal Today, a publication of The Stanford Daily covering
Stanford football.
Education
Klingenstein Institute, TeachersCollege, Columbia University 2010-2011
M.A. in education, emphasis on private school leadership; courses on leadership, finance,
marketing, law, group dynamics, human learning, history of privatization, and philosophy.
Completed practicum in market research and strategic planning culminating in a report to
Midland’s board of trustees reviewing the school’s effort to integrate day students. Wrote
analyses of Midland’s financial situation and its legal and marketing challenges. Capstone project
required two days of on-site study of active head of school through shadowing and interviews.
U of Wisconsin-Milwaukee,Professional Theatre Training Program 1989-1990
Completed half the work toward an M.F.A. in acting, withdrew in good standing
Stanford University B.A. with distinction in political science. 1983-1987

3. Professional development
Klingenstein Summer Institute; Pacific Advanced Placement Institute; Economic Forces in American
History (Foundation for Teaching Economics); California Association of Independent Schools’
Retreat for Experienced Teachers; The Great Depression, World War II and the American West
(Gilder Lehrman Institute of American History); The American Judiciary (Gilder Lehrman); Southern
Regional Meetings of the California Association of Independent Schools (once as a presenter);
served on visiting accreditation teams to Campbell Hall, Wildwood School, and Highland Hall.
Personal
My wife, Lynda, is Midland School’s college counselor; my son, Sean, is a freshman at Stanford,
and my daughter, Emily, a freshman at Midland.
After teaching together at the American School of Guatemala in 1992, Lynda and I spent three
more months in Central America, mostly as volunteer teacher assistants in the parish school of the
Catholic mission of San Lucas Tolimán, Guatemala. In the summer of 1995, we took nine Midland
students to San Lucas for three weeks of volunteer work followed by a week of travel. In 2012, we spent
a month teaching English in Jalisco, Mexico.
I am an avid fan of the San Francisco Giants, the U.S. national soccer teams, and the Sunday New
York Times. I play too much online Scrabble; I recently completed my first marathon; and I am an active
amateur actor, having recently performed in Santa Barbara in the world premiere of 154 and Paradise, a
play by Gerald DiPego, writer of Phenomenon and other well-known screenplays.
References
Pearl Rock Kane
Director, The Klingenstein Center for Independent School Leadership
Teachers College, Columbia University
kane@tc.columbia.edu
212-678-3156
Maria Larios-Horton (former Midland parent)
Director, Multilingual and Migrant Education Programs
Santa Maria Joint Union High School District
marbel3@gmail.com
805-922-4573, ex. 1601
Eric Niles (former Midland faculty)
Head of School, The Athenian School
eniles@athenian.org
925-837-5375
Doreen Oleson
Head of School (retired), Saint Mark’s School
Governing Board President, National Association of Episcopal Schools
doreenoleson@yahoo.com
626-676-5203
Jill Redl (former Midland faculty)
English Teacher, Colegio Nueva Granada
redljill71@gmail.com
805-500-6493