Anna Treesara

Career coach · Chicago, IL · virtual

"Anna Treesara is a former classroom teacher turned edtech professional, entrepreneur, and career coach who is passionate about helping people navigate meaningful career transitions." (in their words, on their website)

Services

ServiceWhat is includedPrice
Career Coaching - 15-minute clarity conversation
professionals exploring career transitions
1 session · clarity conversation on request
Transitioning Teachers Workbook
educators exploring life beyond the classroom
guided prompts · reflection exercises · practical action steps · self-care check-ins on request
Transitioning Teachers Support Group
teachers transitioning out of the classroom
customized one-on-one coaching · resume workshopping · LinkedIn optimization · interview preparation on request
Consulting Services
companies needing project consulting or workshop facilitation
management/leadership best practices · people operations initiatives · instructional design on request

As published on their website, read Sep 30, 2026.

How they compare

Computed by Callings from the prices and experience coaches publish. Not a rating.

Where they fit

StudentsEarlyMidManagerDirectorVP / C-suite
Resume and LinkedInnoyesyesnonono
Interviews and offersnoyesyesnonono
Job search strategynoyesyesnonono
Career direction and changenoyesyesnonono
Leadershipnononononono
Personal brandnononononono

How they work

Process
Book free 15-minute clarity conversation · Clarify strengths and transferable skills · Build confidence to pursue aligned roles
Before coaching
high school English teacher, education (4 years); Customer Success and Business/People Operations professional, edtech and nonprofit education

Do it yourself, or hire a coach?

Doing it yourselfUsually enough whenA coach earns the fee when
Resume4 to 8 hours for a strong base, then about 30 minutes per posting. Callings can tailor it to each job.You are staying in the same field and level and have recent results to cite.You are changing field or level, coming back after a long break, or many applications brought no interviews.
Interviews3 to 6 hours of practice out loud per interview process. Callings can prepare you for each job you track.Early rounds in a format you know.Final rounds, panels, a new kind of role, or you tend to freeze.
Job searchA target list, a weekly plan and steady outreach. Callings builds the weekly plan and tracks every application, free.Interviews are coming in.Three months without traction, or a senior search that runs on your network.

Times are our estimates. Try Callings.

Questions to ask before hiring

  1. What does it cost in total, and what is included? (no published price)
  2. What are your cancellation and refund terms? (no refund terms on their site)
  3. Who do you usually work with, and how long does a typical engagement last? (always worth asking)

What they publish

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