MentorCruise

Career coach in Chicago

Career coaches based in Chicago help online with a job search, an internal move, or the story you tell in interviews.

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Coaches listed
9
Sessions
Online
Intro call
Free

Our mentors work at

In Chicago

Career coaches based in Chicago

9 coaches based in Chicago.

Leoson Hoay
5.0

Leoson Hoay

Tech Lead (AI & Data Science) at Learning Collider

Chicago, Singapore

Data Science LLM AI

Hello there! 你好！はじめまして! I am an AI Deployment Engineer and Data Scientist, and previously a Tech Lead at the University of Chicago Urban…

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Jared Shay
5.0

Jared Shay

VP of Engineering

Chicago, United States of America

Rails Ruby Artificial Intelligence

With over 15 years of experience, I'm a passionate technologist with a robust engineering background. My journey has taken me from the ince…

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Simon Lepkin
5.0

Simon Lepkin

Executive Coach for Software Engineers, Ex-Upstart

Chicago, United States of America

Influence Without Authority Managing Up Software Engineering

I started my engineering career in 2013 at Upstart, building it from 4 engineers to 400. I’ve contributed, led, and managed Product, Data, …

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Steve Sobel
5.0

Steve Sobel

Director of Engineering at Toast

Chicago, United States of America

Leadership Engineering Leadership Product Strategy

I have 25+ years of experience as an individual contributor, manager, and director in software engineering. I'm passionate about providing …

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Jeremy Abrams
4.8

Jeremy Abrams

Senior UX Director at Prosper Marketplace

Chicago, United States of America

Figma UX Design UX Strategy

UX Director with over a decade of experience designing and scaling tech products. I currently lead a diverse, high-impact UX team at Prospe…

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Carrie Berg
5.0

Carrie Berg

VP of Learning and Development

Greater Chicago Area, United States of America

Learning Talent Human Resources

Carrie Berg is a seasoned executive with over 20 years of experience in sales, marketing, strategy, commercial effectiveness, learning and …

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How it works

Learn from someone who has done the job

Every mentor lists their price upfront, and they offer a free intro call, so you can talk before you pay. Once you start, you work with the same person every month.

  1. 01 Search by role, company or skill
  2. 02 Check availability and book an intro call
  3. 03 Meet your mentor as often as suits you
01 · Discover
Browse
Product manager
Free intro Top mentors

Leoson H.

Tech Lead (AI & Data … · Learning Collider · 5.0

$170/mo

Jared S.

VP of Engineering · 5.0

$310/mo

Simon L.

Executive Coach for S… · 5.0

$220/mo
02 · Start
Profile

Leoson Hoay

Tech Lead (AI & Data Science) at Learning Collider

Free intro · $170 / month

4 spots open

03 · Meet
Messages
I'm putting together my case for a staff promotion. Could you review it before I submit it?
Of course. Send me the draft by Thursday and we'll go through it together on our call.
Thank you! Same time next month too?
Sounds good. Bring any feedback from your manager and we'll plan the next step.

From mentees

What mentees say

My session with Jared was instrumental in helping me gain valuable insights and direction for my career development. We discussed how to update my resume to showcase the …

Anukiran

With Jared

Jared was available on very short notice for a hands-on session to help me with some questions about and preparations for my career situation. It was, as always, …

Rich

With Jared

Totally in line with my expectations for an efficient and warm-hearted conversation. Can't wait to continue with my mentorship.

Grigor

With Jared

Questions

Questions about coaching in Chicago

Can't find your answer? Send us an email.

Are sessions with a career coach in Chicago in person?
No. Sessions are online. The coaches on this page are based in Chicago, and you meet them by video.

Can I talk to a coach before I pay?
Yes. Every coach offers a free intro call, so you can talk before you decide.

How do I choose a career coach?
Read their background, check that they have open spots, and book an intro call with one or two people.

Can a Chicago career coach help with an internal move?
Yes. People use these coaches for a search outside their company and for a move inside it. Sessions are online.

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Other places

The same coaches, listed for the other cities in this experiment.

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Talk to a coach before you decide

Every coach offers a free intro call, so you can see if the fit is right.

Browse career coaches Get matched