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Meet the founder of Tutoring Tree, LLC,


Anna Treesara is a former classroom teacher turned edtech and tutor/entrepreneur. She loves connecting with educators and helping them discover how to make a positive impact beyond the classroom walls! Trying to transition out of the classroom? Book a FREE 15-minute initial consult here:


You can also reach out directly through Anna's LinkedIn or via email at

Anna Treesara was born and raised in Chicago and is a former high school English teacher who taught abroad in Thailand for one year and in Chicago for three years. She transitioned out of teaching in February 2018 in hopes of creating a larger and more meaningful impact beyond the classroom walls. 

Since leaving the classroom, Anna has continued to work in education, specifically in nonprofit and edtech spaces and in both Customer Success and Business/People Operations. While she was at an edtech company and helping build and scale the Customer Success team, she discovered that her favorite part of being a manager was helping former teachers transition into an environment outside of the classroom. As a result, Anna ventured into career coaching in late 2021 and has coached dozens of teachers, helping them successfully land fulfilling and impactful roles through customized one-on-one coaching, resume workshopping, LinkedIn optimization, and interview preparation.

When Anna is not career coaching, you can find her hanging out with her husband Kyle and their sassy Shiba Inu Addison, working out/running on the 606, or reading and trying new restaurants with her book club Brunchin' Bookworms.

To learn more about Anna's services, book a FREE 15-minute initial consult at


Transitioning Teachers Workbook

Not sure where to start and not quite ready for 1:1 career coaching just yet? Purchase Anna's workbook, which includes recommended action items, reflection questions, and self-care check-ins in every chapter.


The guided prompts and exercises in this workbook will allow educators to be intentionally introspective and start taking immediate next steps toward a career beyond the classroom walls.

Looking for more ways to connect with transitioning teachers and have access to job opportunities that are perfect for educators?! 

Anna posts job opportunities CONSTANTLY and as soon as she sees them! This means that you may see job postings faster and have a better chance of landing a job as you could be among the first few applicants.

Why else should you join this Slack group?

  • Learn the ins and outs of Slack with other transitioning teachers just like you. Many companies (especially edtech) will use Slack to communicate!

  • Be a part of a community where everyone is experiencing similar challenges and can lean on each other for support.

  • Get tips, tricks, and job opportunities as soon as Anna sees them instead of just waiting for Anna’s newsletter to come out.

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