All Episodes
Pretty Rich Teacher — 97 episodes
097: From Music Teacher to Customer Success: Proof You Can Pivot Into Edtech No Matter What You Teach
096: 7 Thoughts Making It Hard to Break Into Edtech as a Teacher
095: Teachers, Let’s Talk About Money: The Money Conversation ALL Educators Need to Hear.
094: You Don’t Have to Wait for Life to Get Easier to Leave the Classroom | Keysha’s 4 Month Edtech Transition Story
093: The 4 Reasons Teachers Aren’t Using Their Experience to Make $100K
092: How to beat the back to school blues 4 steps to creating a pretty rich exit plan that actually works
091: How Caylin DIY-ed Her Teacher Exit Into EdTech in Less Than 4 Months as a Single Mom
090: Putting Herself First: From Assistant Principal to Customer Success
089: How Lauren Got Six Figures, Lost 15 Pounds, and Started a Business in 90 Days
088: How to be Swimming in Interviews + Job Offers this Summer
087: Teacher to Corporate: The Story Behind My Six-Figure Career Pivot
086: The 5 Real Reasons Teachers Quit Their Transition Journey into Corporate
085: How to Leave a Career or Relationship That No Longer Serves You
084: Teacher Girlies, it's Time for a Pep Talk
083: How Cassi Transitioned out of the Classroom and into EdTech Corporate
082: Why You're Getting Interviews (and NOT Job Offers) Part TWO
081: Three Reasons to DIY your Career Transition vs Paying for Support
080: Pretty, Paid, and in Tech: Customer Success Panel with Former Educators
079: Pretty, Paid, and in Tech: From Teaching to Six-Figure EdTech Sales Careers Panel
078: How to Invest Thousands in your New Career on a Teacher Salary
077: The 7 Truths Transitioning Teachers Need to Hear to Leave the Classroom by August
076: How to Know If You Would Be a Good Fit for EdTech Customer Success or Sales as a Transitioning Teacher
075: What Roles You’re Actually Qualified for as a Teacher & How to Use Your Education Degree in Corporate
074: 5 Reasons to not Feel Bad About Leaving your Teaching Career
073: How to Decide if you Should RENEW your Teaching Contract
072: How to ACE your Corporate Interviews in 2026 as a Transitioning Teacher
071: 7 Reasons Why You Haven't Landed the Interviews or Job Offers you Want as a Transitioning Teacher
070: How to NOT Burn Bridges as an Educator Leaving Education for Corporate
069: How to Transition into a New Career As a Teacher by Next School Year
068: How to ask for what you deserve in your dating life and your career with Torah Cents
067: What to Do If Your Career Transition Is Taking Longer Than Planned
066: How Carla DIY'd her Transition into corporate as a transitioned teacher
065: What Actually happens your first 90 days as a transitioned teacher working in corporate
064: What EdTech Hiring Managers are ACTUALLY looking for in transitioning teachers
063: The Top 10 Reasons Teacher Career Transitions FAIL and How to Succeed in 2026
062: Five Ways to GUARANTEE a Successful Transition Into Corporate as a Teacher
061: How to Create Your Exit Plan Into Corporate as a Teacher in Less Than 30 Days
060: The Truth About Corporate Layoffs, Job Safety, and the Government Shutdown — What Transitioning Teachers Really Need to Know
059: Why You’re Getting Interviews (But Not Job Offers) And How to Fix It
058: How Jada became a standout EdTech CSM candidate with only 4 years of teaching experience
057: Rich Teacher, P.O.U.R Teacher: The Mindset difference between being underpaid or paid well
056: How to Stop Being Ghosted by Recruiters as a Transitioning Teacher
055: Rejection Sensitivity: What It Really Means for High-Achieving Teachers in Transition
054: The Scary Truth About Staying ‘One More Year’ (Why It Gets Harder, Not Easier)
053: How to Heal the Sunday Scaries (for Good)
052: How to Choose Freedom over Fear as a Veteran Teacher thinking about Transitioning out of the classroom
051: The Truth About Fear: Why Leaving Teaching Feels So Scary
050: The 5 Core Skills That Will Get You Hired Fast as a Transitioning Teacher
049: Why I Hired a Career Coach (Even After DIY’ing My Transition)
048: How to Actually Use LinkedIn to Land a 6-Figure Role
047: Resume Writer vs. Career Coach vs. DIY: What You Actually Need to Land the Job
046: How Ashley ( A Guidance Counselor) Let Go of Her Timeline and Landed Her Dream EdTech Role
045: How To Make Six Figures as an Educator with a Victory Mindset
044: From Fear to Freedom: Funké’s Journey from Veteran Teacher to New EdTech Career in less than 60 Days
043: How to become Classroom Optional
042: Two Years In: Jasmine’s Pivot from the Classroom to Career Freedom
041: How to Heal Timeline Heartbreak
040: Teacher Retirement Myths: What Really Happens When You Leave the Classroom
039: 5 Habits of Educators Who Made the Leap into Six Figures
038: How Sasha used being a Single Mom as her fuel to invest time and money to make six figures as a transitioning teacher
037: How Jazmin's personality landed her a six figure career in less than 6 weeks
036: How to Become a Pretty Rich Teacher NOW
035: How Samiya used healing, hard work and faith to land her six figure offer in less than 2 months
034: Teacher interviews vs. Corporate interviews: how educators unknowingly self-sabotage in EdTech interviews—and how to fix it
033: Part 2 of Leaving Education + Earning More: How I Hit Six Figures Every Year as a High Achieving Woman of Color
032: Leaving Education + Earning More: How I Hit Six Figures Every Year as a High Achieving Woman of Color (Part 1)
031: How to Quit Teaching Mid-Year (Without Guilt, Shame, or Panic)
030: The Mindset and Strategy Required to ACTUALLY leave education for Edtech this year
029: Six Powerful Reasons Why Leaving Teaching Feels So Hard (and how to make it easy)
028: 4 Reasons You’re Struggling to Land Job Offers (And How to Fix It)
027: How Teachers can Pivot into HR and EdTech without another degree
026: How to Interview Like a Six-Figure EdTech Pro (Even if You're Still in the Classroom)
025: The Six-Figure Role Educators Overlook (But Shouldn’t)
024: Burnt out educators, it's time for a pep talk
023: Three Ways to Step into your new role in EdTech with CONFIDENCE
022: The Support you ACTUALLY need to successfully transition into EdTech beyond just a Resume...
021: Why Your Teacher Resume won't Land you Interviews in EdTech ( and How to Fix it)
020: Applying for Jobs vs. Making a Career Change: Why You're Stuck and How to Move Forward
019: All about Customer Success in EdTech
018: Facing Fear, Guilt, and Regret: How EdTech helps you ease into a new career path that feels safe
017: The 4 biggest mistakes educators make navigating breaking into edtech and how to fix them
016: How Eboni quit her job as a Kindergarten teacher in June and landed a job offer as an Educational Consultant by August
015: How Tambra landed a 100k job offer in Customer Success with her K-12 Experience + Expert Interviewing skills
014: The Power of a Six-Figure Mentor – Lessons Learned & The Story Behind My Elevate Into EdTech Mentorship Program
013: How Santanna Secured a 10K salary increase as a transitioned educator in the EdTech Industry
012: How to make a Six Figure salary and Have more Time Freedom as a transitioned educator working in Edtech
011: How to find peace, faith, and happiness in your transition out of education
010: The 5 Mindset Blocks that stop educators from successfully transitioning out of education
009: Three Tips to help effectively prepare for your EdTech Interviews
008: The 3 Skills Educators need to invest in to land job offers in the EdTech Industry
007: The Top 4 Misconceptions Educators have about transitioning out of education and into EdTech Careers
006: How to negotiate your first corporate salary with confidence as a transitioning educator
005: How Tierre healed her burnout as an administrator and transitioned into a new EdTech career in just 4 months
004: How Hillary landed her first 100k role in Edtech as a transitioned teacher
003: How to Create an Interview Getting Resume for EdTech
002: What is EdTech? + How educators can break in with their education experience alone
001: How Jazmyne broke into six figure career paths in the EdTech Industry with her education experience alone