Ashley Pinakiewicz

Ashley Smallwood is a multifaceted professional with extensive experience in consulting, facilitation, and education. As the Founder and Creative Strategist at Looking Glass Strategy, she partners with educators and design specialists to create meaningful change in education organizations.1

Professional Background

Ashley has spent over 15 years growing businesses and has a diverse professional history:

• Consultant at IDEO: She began her career at the design and innovation firm IDEO.1
• Consultant at Clear USA: She worked as a consultant for this organization.2
• Head of Creative at Tough Mudder: Ashley held this position at the fast-growing startup.2
• Founding 7th Grade English Teacher: She taught at Girls Prep Bronx Middle School.2
• Director of TC NEXT: At Teachers College, Columbia University, Ashley led a department and built a reimagined career center.2

Expertise and Skills

Ashley is known for her skills in:

• Facilitation
• Design thinking
• Education
• Strategic planning
• Collaborative innovation
• Brand strategy

She is committed to advancing equity through collaboration and has received training in inclusive and liberatory design and leadership.2

Education

Ashley holds the following degrees:

• BA in English and Art History from Georgetown University
• M.Ed. from Harvard University2

Current Work

Through Looking Glass Strategy and her role as Principal Consultant at The Group Forward, Ashley:

• Partners with various organizations to unearth meaningful insights
• Designs and facilitates team and organization-wide convenings
• Guides strategic planning processes
• Creates conditions for collaborative innovation
• Builds capacity to help teams work better together23

Ashley is based in New York, where she lives with her partner and young child.2