4 Key TeachMe.To Executives

TeachMe.To is a private company founded in 2022 that offers an in-person leisure learning platform connecting students with professionals for private lessons in sports, music, and other activities. Headquartered in San Diego, TeachMe.To helps users discover coaches based on skill level, group size, location, and scheduling needs.

The TeachMe.To leadership team blends deep expertise in technology, consumer marketplaces, and partnership development. Comprising founders, seasoned technologists, and industry-focused executives, the management team has driven rapid growth, platform innovation, and strategic expansion into multiple lesson categories—all driven by a clear vision to democratize in-person skill-based learning. Their combined backgrounds cover entrepreneurship, venture funding, sales leadership, and marketplace platforms, positioning TeachMe.To at the forefront of its sector.

Key Executives

Tyler Maloney - CEO

As CEO, Tyler Maloney leads TeachMe.To’s vision and strategy, guiding the company through ongoing innovation and high-velocity expansion. Under his leadership, the platform has scaled to over 250 daily lessons across more than 100 cities, maintaining a leading instructor rating and driving TeachMe.To’s emergence as a top in-person learning marketplace. Maloney has also championed key partnerships and the diversification of lessons, notably expanding into music and surfing.

Tyler Maloney holds a Bachelor’s degree in Materials Science & Engineering from North Carolina State University and an MBA from Stanford’s Graduate School of Business. As a serial entrepreneur, he co-founded Undercover Colors and founded Faves, collectively raising over $25 million in venture backing across his ventures. Prior to TeachMe.To, he led multiple technology startups and built a decade-long track record in early-stage consumer and technology companies.

Nick O’Brien - COO

As President & COO, Nick O’Brien is responsible for TeachMe.To’s daily operations, corporate development, and executing the growth roadmap. He drove the business from inception to more than $4 million in GMV, delivered over 50,000 lessons in two years, and grew the team significantly, all while establishing TeachMe.To as the global leader in pickleball instruction. O’Brien also managed city expansion and rapid team scaling during pivotal growth phases.

Nick O’Brien graduated from Vanderbilt University and subsequently co-founded Alloi and Boxtrot, cultivating deep expertise in marketplace platforms and consumer services. His background spans advisory roles and serial entrepreneurship in hospitality and technology sectors, providing him with a well-rounded foundation for his executive leadership at TeachMe.To.

Alex Kaplan - CTO

As CTO, Alex Kaplan leads the end-to-end architecture, development, and scalability of TeachMe.To’s technology platform. Kaplan spearheaded the company’s migration to a microservices infrastructure, which reduced page load times by 40% and enabled more agile addition of new lesson categories and features, ensuring reliable performance as the user base grows.

Kaplan earned his Master of Science in Computer Science from the University of Southern California. He previously served as Lead Software Engineer at MyTutor and Senior Architect at Learnify, and has 8+ years of experience designing and scaling large educational technology platforms.

Nora McTwigan - Head of Sales and Partnerships

As Head of Sales and Partnerships, Nora McTwigan drives revenue growth by building exclusive partnerships with sports clubs, music schools, and fitness studios. She successfully negotiated over 50 partnership agreements in her first year, generating a 60% increase in new coach listings and helping TeachMe.To expand its lesson inventory.

McTwigan holds a Bachelor’s degree in Business Administration from Emory University. Before joining TeachMe.To, she held the position of Director: Field Leader of Hospitality for West Coast Operations at RH and worked as a hospitality consultant. Her expertise spans 10+ years in sales strategy and partnership development for hospitality and lifestyle-focused organizations.

Company Leadership

The TeachMe.To leadership team is composed of experienced entrepreneurs and industry experts who guide the company’s strategic growth, technological innovation, and partnership ecosystem. Their structure fosters agility and collaboration across operations, technology, and business development, ensuring that the company rapidly adapts to market changes and delivers an excellent learning experience for its users. Through dynamic management and cohesive teamwork, TeachMe.To continues to set benchmarks in the in-person leisure learning space.

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