Career Advancement Center
Career Advancement Center
Advancing Your Impact in Education
At Teach For America Greater Chicago–Northwest Indiana, we support our alumni as they grow as leaders and pursue impactful roles throughout the education landscape. Our career advancement resources are here to help you take the next step whether that means deepening your impact, expanding your skill set, or exploring new leadership opportunities.
From school-based roles to policy, advocacy, and nonprofit leadership, we’re here to help you move forward with clarity, confidence, and community.
Upcoming Events
Career Resources
The 5 R’s Framework
Your roadmap for this page. The 5 R's guide you through your career advancement journey — whether you're exploring, preparing, or growing into new leadership — and help you navigate the resources below based on where you are right now.
1. Reflect
Get clear on your goals
(Vanderbilt Career Center, Katharine Brooks & Grace J. Foy, 2020)
An interactive workbook with quick, creative visual thinking exercises to help you clarify your goals, uncover insights about yourself, and take the first step toward career clarity and confidence.
Identify the skills you already have that translate across roles and sectors.
A region-specific guide highlighting key roles across education leadership, policy, and nonprofit sectors — helping you explore advancement opportunities, deepen your impact, and plan your next step.
3. Reach Out
Get feedback and support
Free Resume Review (The Job Helpers)
A free external tool for getting outside eyes on your resume.
4. Role Application
Take the next step
Navigate Your Next Teaching Opportunity
A step-by-step guide for current 2CM and Alumni Educators exploring their next teaching role.
An external job board for education roles across the country and in Illinois.
5. Repeat
Share a job or find your next opportunity through the alumni network.
Alumni
Looking to stay connected or explore new opportunities? Join our alumni LinkedIn group to access weekly Opportunity Blasts, engage with fellow alumni, and share roles, events, and updates across our network.
Employers
Hiring at your organization? Use our content submission form to share job openings—we’ll feature them in alumni-facing career communications and resources.
Workshops
Career Coaching
Alumni can sign up for a 1:1 with a NACE Certified Career Coach.
Our Coaches offer individualized support based on your career pathway, schedule time to speak with one today.
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Diana Diaz
If you just finished the corps or are seeking general career coaching support such as resume critique or interview prep, Diana is your person!
Diana (she/her/ella) is a proud first-generation college graduate born in Mexico and raised in Chicago’s Gage Park neighborhood. Having experienced firsthand the doors education can open, she is passionate about making opportunities accessible and supporting alumni as they envision their own impact in education. She holds a bachelor’s degree in International Business and Marketing and began her career in marketing before transitioning into education, serving as a College & Career Counselor. In her current role as External Affairs Manager, Diana supports alumni engagement and public affairs initiatives while bringing a wealth of knowledge in career exploration and resources to her coaching practice. Outside of work, she enjoys playing soccer and spending time with her husband and two dogs.
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Caryn Lichtenberg
If you are in the classroom, interested in school leadership down the road, or want to understand how to grow your impact in schools, Caryn is your person!
Caryn (she/her) is the Managing Director of Alumni Leadership and brings 15+ years of experience in teaching and nonprofit leadership. She began her career as a 2008 Teach For America corps member in the Bay Area and has since served in the Chicago nonprofit sector at City Year before returning to Teach For America, where she supports alumni in staying connected to their commitment to education. Her background in career coaching deepens this work, as she helps educators and leaders navigate professional growth and change with clarity, connection, and purpose. She holds a bachelor’s degree in Psychology from the University of Illinois Urbana-Champaign and currently resides in Chicago with her husband, two energetic boys, and their goofy dog, who keep her grounded and inspired.
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Jasmin Rosales-Montas
Jasmin (she/her/ella) is a proud first-generation college graduate with Mexican roots from Chicago’s Little Village neighborhood. She has dedicated over 12 years to policy, advocacy, and organizing, and currently serves as Managing Director of Public Affairs, where she helps lead the region’s state funding requests and alumni engagement strategy. Jasmin is a 2021 Negocios Now “40 Under 40” honoree and an alum of the Surge Fellowship Class of 2024. She also serves as the Vice President of the True Value Boys & Girls Club Council, the very club she grew up attending. Jasmin holds a Bachelor’s degree in Psychology from Syracuse University and a Master’s in Public Administration from DePaul University.