Kelly Cassaro

Cues and Views

Education and workforce industry leader Kelly Cassaro, in brief.

Kelly Cassaro

Home: Long Island, NY.  Age: Coming up on 40!  Birthplace: Pittsburgh, PA.  Organization: Generation (  Title: Chief of Learning.  Pronouns: She/Her/Hers.  Alma mater: Ohio Wesleyan University (B.A.); Bank Street College of Education (M.Ed.).

Current project: Writing Shift Teaching Forward to give educators the knowledge, insight and practical advice to prime students for the employability skills they need to thrive in tomorrow’s workplace.  Recent professional development: Currently learning alongside incredible women in the Chief network.  Latest contribution to others: My children James and Grace just collected over 500 pounds of food for the Long Island Cares food pantry.  What’s been your big (or biggest leap)? Moving from K-12 education to the workforce industry.  Hobbies: Cooking in the kitchen with vegetables grown by my husband, Michael.  Recent travel or adventure: Enjoyed the Costa Rican wildlife with my family.  Last book read: Atlas of the Heart, Brené Brown.

What one word would your closest friend use to describe you? I just asked her.  She said “driven, followed by fabulous.”  How do you define a perfect friendship? Being your authentic self. What is your greatest joy? Raising my children.  What is your guilty pleasure? The Hallmark channel.  What word or phrase do you use far too often? It is what it is.  What natural talent have you neglected? I used to be pretty good at the alto saxophone!  How do you relieve stress? Working out.  What is your go-to workout? Alternating between yoga and weight training.  

What was your first paying job? Starbucks barista.  What book have you repeatedly read? Gift from the Sea, by Anne Morrow Lindbergh.  What’s prominently featured on your home or office wall? My children’s artwork.  What’s the best advice you received growing up? Do no harm.  Take no sh%!.  What is your favorite app? Mozzarella sticks 😉.  What is your go-to source of creative inspiration? My yoga mat.  What world event has had the greatest influence on your life? The pandemic, by forcing re-prioritization and accelerating shifts in the workforce.

What is your big idea?

We limit students by placing them on a binary path: either college or career.

What change are you working on to effect in your profession or field? Using my voice so that others can acknowledge and remove the barriers learners face on their lifelong learning journey to open up access for all (employability skills, social capital, digital skills, and more).  What change would you like to see in the world? Greater respect for educators. What mega-trend most excites you? Giving employees greater flexibility and agency in their work. What mega-trend most concerns you? Intolerance of difference and not leaning into discomfort.

What actor would you choose to play you in the movie about your life? Danica McKellar (as she was playing Winnie Cooper in The Wonder Years).  As a kid, what did you first want to be when you grew up? A teacher, which I proclaimed at five years old.  How would you choose to spend tomorrow, if you knew it was your last day on earth? Cooking and eating Italian food with my closest friends and family by the sea.  What advice would you give your younger self? Trust yourself and use your voice.

Personal motto: I can do hard things.  Favorite quote: “Everyone you meet is fighting a battle you know nothing about.  Be kind.  Always” (variously attributed to Plato, Ian MacLaren and others).

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