PearX S19 alum Learn to Win raises $30M to continue helping large clients use data analytics and AI to improve training and onboarding

June 20, 2024

Founder Stories


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Earlier this week, PearX S19 alum Learn to Win (L2W) announced a $30M Series A round, led by the Westly Group and joined by Pear and Norwest Venture Partners. L2W’s software improves training & onboarding for a wide range of enterprise clients, from the Los Angeles Rams to the U.S. Air Force. They do this better than anyone else by using data analytics and AI to personalize learning effectiveness for their customers.

We first backed L2W in 2019, and now five years later, we are honored to double down our support for them. To mark the occasion, we wanted to reflect on our partnership with L2W and the amazing progress they’ve made over the last five years.

We met the founders of L2W, Sasha Seymore and Andrew Powell, in 2019 when they were students at Stanford GSB. We met as part of a business plan competition and our teams hit it off. They’d been chewing over the concept behind L2W for years, but they finally got it off the ground in 2018 while at the GSB.

Sasha & Andrew at Stanford GSB

We met them when they were just two co-founders and an idea with a little traction, and we decided to back them for a few major reasons:

  • First, the founding team was fully dedicated to pursuing the idea: Sasha and Andrew met their freshmen year as Morehead-Cain scholars at the University of North Carolina at Chapel Hill, and they were roommates throughout undergrad. They started discussing the concept of L2W during that time. Following graduation, they went their separate ways: Andrew to Mauritius and Sasha to play basketball in Europe. Although they were apart for three years, they continued to discuss the company and what it could be. And then completely by coincidence, they were both accepted into Stanford GSB at the same time and decided to room together once again. It felt like fate, so they were drawn to pursue L2W officially. 
Founders while students at UNC
  • Second, they solved a problem that they were passionate about: Andrew was really interested in education and had spent three years at The African Leadership University in Mauritius designing new learning models. Sasha was a basketball player at the University of North Carolina at Chapel Hill, had spent time studying the possibilities of peace through sports.They combined their passions in education and sports to create a new method for training athletes. Their initial pitch to us was: Learn to Win is a “Rosetta Stone” of playbook learning, turning playbook and gameplan materials into an interactive learning experience and providing coaches insight and analytics into what their players understand and what they do not.
  • Lastly, they knew the market was huge. While they started by focusing primarily on sports teams, they knew that there were many zero tolerance environments and industries used training tools that don’t match the demands they face. The L2W team had a vision to expand to industries like the military, aviation, and oil and gas. 

L2W pitch deck in 2019

They applied and were accepted into PearX’s Summer 2019 cohort. At the time, they knew they had a big opportunity in front of them, and they’d gained some early traction with a few clients.They wanted to use their PearX experience to really hit the gas and accelerate their company forward. Through the 14 week PearX cohort, they onboarded many new customers to their microlearning modules, and by the time Demo Day rolled around, they had 100+ clients and over $1M in sales. They also expanded beyond sports during PearX and signed a large contract with the U.S. Air Force. 

2019 PearX Demo Day pitch

PearX S19 cohort, which included companies like Windborne, Polimorphic, Learn to Win, Xilis, and Gradio.

Following Demo Day, they raised a $4M seed round in 2020 led by Norwest Venture Partners and joined by Pear and 20|20 Fund. They continued working out of Pear’s offices in Palo Alto for a period of time, so we had the chance to work side by side with the team and see their progress. Over the following few years, they grew from a team of 2 into a full-time staff of 30+. They continued to refine and evolve their product, and onboarded hundreds of enterprise clients like Chick-fil-A, the U.S. Department of Defense, and professional sports teams like the Carolina Panthers. In the last few years, they’ve expanded and refined their platform, involving even more learning science and AI to better help customers with their training. 

With this latest $30M Series A fundraise, we know they’ll be able to take it even further. Their path has been exciting to witness and we are excited to see where they take the tool next.