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January 29, 2021
Training on the Front Lines: Announcing our Investment in Learn to Win
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This past year has been anything but static. Folks on the front lines are expected to react in real-time, often amid changing circumstances. For many, the stakes are high. In these moments, it can be difficult to recall what was written in a training manual or scribbled on a whiteboard. That’s why we are so excited to lead Learn to Win’s $4M seed round. The company’s active learning platform helps pilots, athletes, and business people alike stay on top of their game.

The Team 

As a basketball player at UNC, Learn to Win Co-Founder and COO Sasha Seymore needed to be ready to face a different team each week. Doing so required him to learn a carousel of new plays and understand the strengths of his upcoming opponent. Despite these dynamic requirements, his coach handed him a large, static binder full of X’s, O’s, and arrows.

Sasha’s co-founder and CEO Andrew Powell has long focused on excellence in education. As student body president at UNC, he promoted high-structured blended learning throughout the university, worked with Coursera, and joined the African Leadership Academy full time after graduation, where he opened accredited universities in Mauritius, Kenya, and Rwanda.

Learn to Win Co-Founders

Sasha and Andrew have known each other since high school, but they started Learn to Win while in school at Stanford GSB. They recognized that existing learning and development offerings don’t meet the needs of a mobile-first generation.

The Problem

Legacy Learning Management Systems (LMS) are often clunky and hard to update. Even mandatory content modules can fail to prepare trainees for the job ahead. Trainers are left with little information beyond completion data to understand training effectiveness. Layering on security requirements of many industries, access can sometimes be restricted to inconvenient on-premise solutions. Amid COVID, that inconvenience turns impractical.

Unsurprisingly, the market remains highly fragmented. Large human capital management (HCM) players offer LMS solutions bundled in their product suite. Many enterprises stick to these suboptimal solutions to reduce cost and complexity. The long tail of alternatives is extensive, and often undifferentiated.

Active Learning Solution

Learn to Win stands out for its mobile-first platform that provides both a content creation engine and data analytics suite to build and deliver customized training materials. The software includes authoring tools for coaches, managers, and other trainers to input historical training materials and parses them into bite-size learning, both lessons for formative learning and quizzes for more formal assessment. Sessions are three to five minutes in length, allowing for short but frequent engagement designed to improve learning and information retention.

Initially, Learn to Win started in sports – now working with elite collegiate and professional athletics programs including the Carolina Panthers and Pittsburgh Penguins. Sasha and Andrew leveraged a popular entrepreneurship class at Stanford, Hacking4Defense, to introduce the solution to the Air Force. They have since taken advantage of interest from other areas of the military as well as the private sector to develop Learn to Win into a versatile platform. 

Training (and importantly, retraining) will be critical for the next generation of talent. To us, it is no surprise that Learn to Win’s engaging, accessible platform has thrived in the accelerated transition to remote learning. We look forward to partnering with this powerhouse team so that when it’s crunch time, elite performers are ready to go.

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