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Woman of the Month 2-08: Kim Kleeman, president and founder, Shakespeare Squared

Kim Kleeman, a former elementary and secondary school educator, is the founder of Shakespeare Squared, a Glenview, Ill-based education development company. Its 20-person staff and more than 400 freelancers create everything from lesson plans to text books to web sites for publishers. We talked with Kleeman about how she made the transition from educator to small-business owner and forged her successful niche.

Q. Where did you grow up, go to school, and what led you to your first career in teaching?

A. I grew up in Glenview, IL, and earned my bachelors and masters degrees in education from Loyola. I was drawn to teaching because of its more predictable schedule. I thought it would be a better fit for me while raising a family. I wanted to avoid the instability that can coincide with being an entrepreneur, which is what my parents were for over 40 years. I taught in Glenview (PreK-8) and Wilmette (high school) schools, and Regina Dominican High School after college, where I was also the speech and debate coach.

Q.What personal and professional factors influenced the launch of Shakespeare Squared?

A. My husband is also an educator. During the time he was student teaching, it really strained our budget. He couldn’t work anywhere else. We subcontracted for an education publisher, proofreading textbooks after we put our children to bed. It turned into much, much more work than we ever imagined. At the time I was looking for more flexibility in my schedule, as our oldest daughter was diagnosed with juvenile rheumatoid arthritis, and I needed to take her to doctors and so forth. So I decided to turn what started as freelance work into a home-based business. In 2005 I expanded to a 1,600-square foot office with a staff of 3 (including myself).

Q. Did you have assistance starting a business, either financial or otherwise, or were you able to launch it on your own?

A. It started as a home-based business, which required no extra financial investment. I moved to an office in 2005 that required $4,000 in overhead. I borrowed another $5,500 from my father to help with the payroll. Now I have a 5,200-square foot office, 20 employees, and over $2 million in annual revenue.

Q. How has the business evolved?

A. Initially, Shakespeare Squared was hired to perform basic editorial services such as editing and proofreading. Our services expanded to content creation and development. Now, S2 is more involved with concept and product development from the ground level. I also founded two “sisterapostrophe organizations. The Shakespeare Squared Foundation offers teaching scholarships and awards for student teachers, and UpGrade Education, Inc., offers professional training for writers, editors, and educators for the educational publishing field. All three organizations are linked by my mission to being an innovator and change agent in the education industry. It’s my goal to remove the obstacles that stymie educators and working parents so that I can utilize this source of untapped talent and offer innovative products that meet current standards and the customized needs of our clients.

Q. How are work/life balance issues taken into account in your business life?

A. I founded Shakespeare Squared initially as a solution to the problems I faced while juggling the demands of career and family. In the years since, part of my mission has evolved to address the obstacles that face other working mothers. My staff, which mainly consists of women, are offered flexible hours, telecommuting options, and there’s even a “parent’s room,apostrophe complete with a crib, toys, and playpen, in case someone needs to bring their child to work. Our team of freelancers—mostly educators and publishing professionals—flexes according to current project needs. By offering flexible hours and benefits that provide better work/life balance, I can utilize an untapped source of talent and increase employee retention.

Q. What are the issues in education you are addressing with this business?

A. Education standards constantly change, and they also vary from state to state. Standards are changing rapidly primarily because of the No Child Left Behind Act. Our team of experienced educators is current with these standards.

Q. What were the biggest challenges you faced and what were the greatest strengths you brought to the business?

A. One of my biggest challenges was breaking into an industry (publishing) with which I had no experience. I had to network aggressively to get in touch with the key players. My other challenge is rapid growth. I addressed this by hiring freelancers from an untapped pool of talent: working mothers and former/current educators. Also, it was hard for people I knew to translate the fact that I was going from being a teacher with no business aspirations to a full-time business owner. My greatest source of strength is my family. I meet every morning with my parents for a cup of tea. We discuss whatever issues or challenges the business is facing and brainstorm ideas. My father understands the challenges of owning your own business, and my mom is supportive in every way. My mom, sister, sister-in-law, and best friend from high school are also on staff.

For more information about Shakespeare Squared, go to