TeachMe.To appoints Tyler Maloney as new CEO, Nick O’Brien named President and COO

TeachMe.To, a platform for finding and booking local in-person sports and skills instruction, has announced Tyler Maloney's appointment as its new Chief Executive Officer. 

Nick O’Brien, who has served as the company's CEO since 2021, will be President and Chief Operating Officer.

Tyler Maloney, who brings over a decade of experience in leading early-stage startups, is set to guide TeachMe.To through its next phase of innovation and expansion. Maloney co-founded Undercover Colors in 2014 and Faves in 2019, raising over $25 million in venture funding for his companies.

Expressing his enthusiasm for the new role, Maloney stated:

“TeachMe.To is addressing an enormous void in the marketplace by making it simple for people who eagerly want to learn a new skill or activity, to connect with friendly local experts that are willing to teach.

“It’s an exciting point in the company’s trajectory and I’m looking forward to navigating the business to its next level of success.”

Nick O’Brien, an alumnus of Vanderbilt University and a seasoned entrepreneur, will continue to play a pivotal role at TeachMe.To. O’Brien co-founded Alloi in 2020 and Boxtrot in 2021. As CEO of TeachMe.To, he has successfully grown the business from zero to $4 million in Gross Merchandise Value (GMV), delivering over 50,000 lessons in two years and establishing the company as the leading provider of pickleball lessons globally. 

Under his leadership, TeachMe.To has expanded to a team of 20, operating in more than 100 U.S. cities and offering lessons in multiple sports.

In his new role, O’Brien will oversee daily operations and corporate development.

TeachMe.To, launched in 2023, provides an accessible platform for individuals to find and book local lessons with experienced coaches. The service currently offers instruction in sports such as pickleball, golf, tennis, surfing, music, and other skills.

 The platform also supports athletes and experts by allowing them to monetise their expertise, whether building their client base or starting a coaching career. Top earners on TeachMe.To can make upwards of $5,000 per month.

The company’s mission is to simplify learning new skills by connecting students with the closest, most affordable, and friendliest coaches available. This approach has resonated with users, leading to rapid growth and widespread adoption across the U.S.