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Yael Gilboa Kaufmann: Helping Companies Unlock Employee’s Skills and Talent

Yael Gilboa Kaufmann: Helping Companies Unlock Employee’s Skills and Talent

Hi everyone! I’m Spiffy, your favorite interplanetary journalist reporting from Planet Earth with an eye on entrepreneurs making a difference on UN SDG 8: Decent Work & Economic Growth. Today I’m going to learn how one company is increasing opportunities for employees to learn and develop their skills. Join me as I welcome Yael Gilboa Kaufmann, co-founder and chief operating officer of Learn In. Are you ready to be enlightened?

Spiffy: Hi Yael, it’s a pleasure to hang out with you today. Can you start by telling me what challenges you’re addressing through your work with Learn In

Yael: The pleasure is all mine, Spiffy. As technology continues to rapidly change, we all must learn more, faster—that is true for everyone from K-12 students to employees in the workforce. Businesses spend a tremendous amount of money on training for their employees, and increasingly more in recent years to close the skills gap. We built Learn In to help companies unlock their greatest asset—their talent—by rethinking education benefits and removing the barriers to learning for everyone across an organization.

Spiffy: I’m intrigued! What motivated you to help companies unleash their employees’ talent and curiosity?

Yael: I am passionate about increasing access to opportunity and I’m a firm believer that talent is equally distributed but opportunity is not. My parents are immigrants who instilled in me the importance of education and I am grateful for all the teachers and mentors who have helped me get to where I am. As someone who taught and tutored for a decade, I also appreciate the work that goes into it. I hope to increase my impact by expanding access to learning as a means of unlocking opportunities.

Spiffy: It sounds like you’ve found a pretty good set of keys to unlock these opportunities! How would you say you’re working to create a more equitable world?

Yael: At Learn In, we help companies offer education benefits, including learning stipends. Our learning stipends are essentially prepaid credit cards that remove a financial barrier for employees so they don’t have to pay the upfront cost of a program and wait to get reimbursed. Given that 40% of Americans can’t afford an unexpected $400 expense, this is important to ensure that access to learning is equitable and not just for employees who can afford to pay for the cost of a program upfront.

Spiffy: That’s definitely a deal-maker! Can you tell me about an initiative that you’re particularly proud about?

Yael: We help companies facilitate cohort-based learning with what we call skill academies. Rather than just firing and hiring people as skill needs change (which is expensive and inefficient), companies can teach employees the skills that they need. For instance, if thousands of employees needed to learn data analytics, you could create the XYZ Company Data Analytics Academy to “upskill” or “reskill” them, which helps with employee morale, retention, and is often the better business decision.

Spiffy: I always ask entrepreneurs about failure. Could you share about a time when you faced failure and didn't give up? What have you learned from failure?

Yael: Well, Spiffy, I would like to reframe this away from “failure” as “success” and “failure” are often relative, and both offer opportunities for learning. To be clear, I did not get straight A’s in every class or get into every college I applied to. I didn’t win every race and I have certainly faced obstacles and disappointment many times. The important thing is to not hold things close to your heart. Life happens, you win some, you lose some, and it's all about picking yourself up and finding the silver lining.

Spiffy: Before we sign off, is there anything else you would love to leave with our audience?

Yael: Follow your heart. Life is too short to spend time chasing someone else's dreams, following someone else's passions, or worrying about what everyone else thinks. Optimize for people. Surround yourself with people you trust and admire, both personally and professionally. Invest in yourself and your health—whether it's mental, physical, emotional— don't take your health for granted.

Spiffy: Thanks for inspiring our audience to follow their own personal dreams, Yael. It’s been an honor to speak with you.


Yael Gilboa Kaufmann is co-founder and COO of Learn In, the first talent-building platform designed to remove barriers to employee participation in learning while simplifying how teams build job-ready skills. Yael is an investor turned operator and a lifelong learner who believes that learning neither begins nor ends with a degree. (Nominated by Pathway Ventures. First published on the Ladderworks website on October 4, 2021.)


© 2021 Ladderworks LLC. Edited by Jill Landis Jha. Spiffy’s illustration by Shreyas Navare. Follow Spiffy’s interviews of founders building a more equitable world here.