Hills Learning is co-founded by Jon Hills, Director of the center. It starts as a tutoring service for Japanese and Chinese languages. By the end of the year the center has added Korean and English, and, started to conduct group classes as well as private classes. The center opens at the Chanin Building next to Grand Central, New York.

Hills Learning grows from a small learning center of one room to a larger learning center with five rooms. Thai is added in 2010 and Cantonese is added in 2011. In 2012, Jon Hills is interviewed by PBS for a having a unique learning center focusing on Asian languages and CBS New York writes an article citing Hillls Learning as "One of the best places to learn a foreign language."

Hills Learning starts to work with the accreditation team at MSA to start the accreditation process. Hills Learning revises its curriculum to fit in with accreditation standards, including developing a unique assessment system to track student progress. In 2015 the decision is also made for Hills Learning to move to permanent space with six room capacity at 315 Madison Avenue (next to Grand Central).

As 2016 starts, Hills Learning starts to put all the changes in their educational program in place. Assessments are offered in every group class, both for speaking and writing & reading. A new teaching philosophy of "target language only" is implemented across all classes, and teachers are trained accordingly. After an almost 3 year process, Hills Learning is finally accredited on May 1, 2016.

Hills Learning starts online classes in 2017, so that students not just in the New York area but anywhere in the US (and the world) can take online classes. The online program starts with private classes being taught on Adobe Connect and Skype. In 2017 for the first time Hills Learning staff attend the ACTFL conference in Nashville, TN to learn best practices in teaching and attend multiple workshops. Also for the first time using the new space at 315 Madison Avenue Hills Learning hosts a holiday potluck party in December for all teachers and students. Spanish is added as a regular language.

In 2018 the new Hills Learning website goes live after over a year of development with our website company. The website is a redesign on the outside, and in the inside it is a learning management system for both teachers and students. After being in business 8 years Hills Learning puts in practice automating lesson notes, reminders, welcome notes, feedback forms, calendars, and other learning tools. Hills Learning staff also attends NECTFL for the first time, an event that is more local than ACTFL and has multiple workshops for best teaching practices.

Hills Learning starts offering group classes online through zoom in 2019. Previously, only private classes were available through skype or adobe connect. The group classes attract students from outside the New York area, and give a unique opportunity for learning languages online. Hills Learning also creates its own curriculum in 2019 independent of textbooks, spearheaded by "course plans" which detail out the main points of each semester. Also for the first time in 2019 Hills Learning starts to record all spoken assessments at the end of the semester, and puts into place a review process for all assessments submitted into the system. The Arabic program also starts in 2019.

Everything happens in 2020 when the month of March begins. Although already starting in February the center is being disinfected, rumors begin to circulate that colleges could be closing in New York City due to COVID-19. Even though Hills Learning policy is to follow the NYC Dept of Education, the decision is made to preemptively close in person learning on March 13. After multiple training sessions and efforts from our students and teachers, all classes are effectively online within a week, and running regularly by the end of March. The online classes offer great benefits to students in person classes don't, for example, having the ability to review full recordings of classes.

With the online programs in 2021, Hills Learning starts to develop a student base from around the world. Teaching online also gives the flexibility for our teachers to teach from anywhere, not just when they're in New York City. To facilitate online learning, Hills Learning develops an integration with zoom where recordings are automatically detected and pulled into student and teacher accounts. Hills Learning also develops its own homework system, where students can submit homework assignments and assessments and teachers can grade and give feedback directly through the website. A flashcard system is also developed called Course Links, so students can have access to premade flashcards for vocabulary and phrases per class level in their accounts.