Why are the Pentagon, major league sports teams, and F500 companies embracing microlearning? Interview with Learn To Win co-founder Sasha Seymore.

Sasha Seymore is the co-founder and COO of Learn to Win – a software platform that unlocks the untapped expertise in every organization. A Stanford Knight – Hennessey Scholar

and MBA, Naval Reserve Intelligence Officer, former McKinsey consultant, and proud one-time UNC Tarheel basketball player, Seymore is passionate about gamifying the Last Mile of learning: the critical operational knowledge that drives performance – but is rarely taught.

Learn to Win’s clients include the Department of Defence; sports teams like the NHL’s Pittsburgh Penguins and Ole Miss football; and Fortune 500 companies, such as Chick-fil-A, Novartis, and Regeneron.

Could you tell us a bit about yourself?

I’m the Chief Operating Officer and co-founder of Learn to Win. I lead sales, marketing, and customer success for our company (essentially everything that touches a customer). My background in athletics and the military really fits well with this customer focus.

Prior to Learn to Win, I was a high-level basketball player, and I currently serve as a reservist in the US Navy, so I understand a bit more deeply the problems we’re trying to solve for our customers.

In my past, I also got an MBA from Stanford on a Knight-Hennessy scholarship, worked as a consultant at McKinsey & Company, and spent some time in Northern Ireland studying how athletics could be a tool for healing in former conflict zones.

What is Learn To Win?

Learn to Win is an education technology company focused on the ‘Last Mile’ learning challenge, or the critical operational knowledge that drives performance. Our product is an active learning platform that makes it simple for anyone to build a lesson — quickly and easily — with proven learning science principles to make training more effective for everyone.

Our learners consume content in bite-sized chunks — in the flow of work and on any device.

What led you to found Learn To Win?

The original insight that led to Learn to Win came while I was a walk-on on the basketball team at North Carolina. At a team dinner the week of the first Duke game, I noticed all of my teammates playing Trivia Crack.

Trivia Crack is an app-based quiz game that pits players against each other in short contests that test their knowledge of random facts, like “What’s the capital of Norway?”

I remember thinking to myself, “These guys love this game, and it’s the night before the biggest game of their lives… I wonder if we could develop something they were similarly excited about, but that would actually help them on game day.”

I mentioned this to my roommate at the time, UNC’s student body president Andrew Powell. We came up with an idea to bring a Rosetta Stone-type approach to teaching a sports playbook, but with an authoring system that made it really easy for any coach to build the material.

We didn’t actually build the tool until we headed to graduate school at Stanford several years later. But that initial spark of insight around building an education technology that was fun to use, made creating learning materials easy, and delivered performance benefits when it matters, is still core to our company.

What makes Learn to Win different from other solutions?

Starting with coaches led us to build a platform that’s quite different from traditional learning software in two key ways: the ease of authoring content, and the effectiveness and efficiency of the learning experience.

Most platforms are built for learning and development professionals. Those folks generally have a lot of technical knowledge about how to construct learning content and a lot of time to build training since it’s their primary job. So learning platforms cater to their needs — tons of functionality, all the bells and whistles — but very time-consuming and confusing for a layperson to use.

Coaches, on the other hand, are not generally technology experts. They probably have never used the word ‘pedagogy’ in a sentence, and they don’t have a lot of time to devote to building learning content since they have tons of other responsibilities. They want something simple that works and leads to results on game day.

But here’s how we see the world: most people are more like athletic coaches than L&D professionals. A sales manager teaching their team the best way to position their product, an Air Force commander equipping the next generation of pilots with air combat tactics, an expert mechanic sharing best practices with the junior members of the team — those folks are coaches, too. They’re just coaching on a different subject matter.

That’s why we think Learn to Win has resonated with such a wide variety of customers — it was built for people just like them.

What industries can benefit from Learn to Win?

We really focus on places where:

  1. Learning matters for performance
  2. There’s extensive and proprietary training content
  3. There are bottlenecks to creating and scaling custom training

Outside of our first initial markets in athletics and the US military, we’ve really seen strong traction in training sales teams (industry agnostic) as well as frontline workers across healthcare, life sciences, manufacturing, energy, transportation, and retail food and beverage, among others.

Who are some of your major clients?

We work with partners across the NFL, NHL, NCAA, & PGA, the Department of Defense, and F500 commercial enterprises, such as Chick-fil-A, Novartis, K Hovnanian, and Regeneron.

Can you share a client success story?

Prior to the 2020 hockey season, the Pittsburgh Penguins brought in Learn to Win to help prepare their players for gameday and overcome the challenges of communicating and training during COVID. The Penguins overperformed despite some of the NHL’s worst injury luck. According to Penguins Head Coach Mike Sullivan, Learn to Win helped via…

  1. Competitive advantage: “Learn to Win was a competitive advantage for our team. We gained so much. I strongly believe that it translated into the win-loss column.”
  2. Learning Science: “What I loved about the Learn to Win platform is that it leverages the science on how we optimally learn. And we found that we didn’t have to make the lessons mandatory. The players were having fun with it, and they were going back to these lessons voluntarily, on their own time.”
  3. Overcoming COVID: “Learn to Win was central to how we overcame the challenges of COVID. I can’t say enough about it. It’s an essential aspect of our coaching, and we’re going to utilize it even more going forward.”

Coach Sullivan was recently named Head Coach of Team USA and is planning to use Learn to Win to prepare the squad.

  • Looking ahead to Olympics (1): “Having the ability to push this information out in advance to all our players before they get to Beijing will give us a leg up on our opponents.”
  • Looking ahead to Olympics (2): “The team that gets to their game plan as quickly as they can and becomes a team (in the true sense of the word) as quickly as they can, is going to be the team that has the best advantage to win the Gold.”

You can find additional detail on our partnership with the Pittsburgh Penguins in our webinar with Coach Sullivan from this summer.

Do you have any available opportunities for partners and investors at Learn To Win?

Absolutely. We partner with complementary organizations all the time and have a comprehensive partner program covering referral/reseller partners, technology partners, and content partners.

Learn to Win gives companies an opportunity to augment their own offerings and expand their company reach and value.

What is next on your roadmap?

We’re focused on building a future where anyone can become an expert coach, regardless of their background or experience.

To that end, every new feature we build has to fit into one (or more!) of three buckets:

  1. Easy Authoring
  2. Effective Learning
  3. Actionable Analytics

We’re constantly adding new features along these lines. If you’d like to check it out, you can book a demo at www.learntowin.com

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