From Teaching to Customer Success: A Career Transition Guide

"I never thought I'd leave teaching, but here I am making double my old salary with actual work-life balance."

This was Sarah, a former 8th-grade English teacher, sharing her story during our recent interview.

Like many educators, she found herself at a crossroads—passionate about education but burnt out from the demands of the classroom.

Today, she's thriving as a Senior Customer Success Manager at an EdTech company.

Her story isn't unique.

For a detailed breakdown of how teaching skills translate to customer success, read my comprehensive guide 'From Teacher to Customer Success: Skills That Shine in CSM Roles'

K-12 teachers are currently the #1 most burnt-out profession, with 44% reporting they feel burned out 'always' or 'very often'.

The situation is even more severe for female teachers, who experience significantly higher burnout rates (55%) compared to their male colleagues (44%)

29% of teachers cite student behavior management as a major stressor, while student misconduct and classroom disruptions have increased by 56% in recent years

Also a staggering 90% of teachers believe burnout is a serious problem.

With teacher burnout at record highs and Customer Success roles offering salaries up to $114,000 for mid-level positions, more educators are exploring this natural career evolution.

In fact, recent data shows that 55% more teachers are retiring early or switching careers compared to pre-pandemic levels.

With 18% of teachers considering leaving the profession entirely and another 37% planning to switch schools in the next four years, the education sector is experiencing significant upheaval.

This transition trend is part of a larger movement, as detailed in my comprehensive Customer Success Career Guide that shows various paths into the field.

But is it really as simple as jumping ship?

And more importantly - is 2025 the right time to make this move?

Here’s why Customer Success has become the go-to career pivot for teachers, featuring real salary data, actual job opportunities, and day-in-the-life comparisons.

Whether you're actively planning your exit strategy or just starting to explore options, this guide will show you what's possible beyond the classroom.

The Financial Picture

The salary progression alone makes this career move worth considering.

While U.S. teachers average around $60,000 annually, Customer Success offers compelling compensation at every level:

Entry-Level Positions

• Customer Success Associate: $61,568

• Customer Onboarding Specialist: $59,900

Mid-Level Positions

• Customer Success Manager: $114,193

• Customer Success Trainer: $77,452

Senior Positions

• Director of Customer Success: $156,985

• VP of Customer Success: $197,880

For a deeper look at compensation across different markets, check out my detailed Customer Success Manager Compensation Guide.

Current Market Landscape

The customer success field shows promising growth, with 61% of CS teams expected to expand in 2025.

Major education companies are actively engaging with the teaching community— Pearson's 2024 School Report gathered insights from over 12,000 educators and students, highlighting the deep connection between education and business.

However, competition is fierce—some positions receive up to 3,000 applications.

This makes strategic job searching key.

EdTech Companies Actively Hiring Teachers

Several established EdTech companies specifically seek former educators:

• Powerschool: Serves 15,000+ districts globally, actively recruiting teachers for their 3,000+ team

• Discovery Education: Currently hiring for multiple education-focused roles including Partner Success Managers, Educational Partnership Managers, and Professional Learning Implementation Specialists

  Also values education experience at all levels, demonstrated by former CEO Scott Kinney's journey from district technology coordinator to chief executive officer.

• EdPuzzle: Offers flexible arrangements including contract, part-time, and full-time positions

• Guild Education: Actively recruits former teachers as Student Success Coaches, with 75% of their students reporting that Success Coaches were key to their achievement

• Paper: Hires former teachers for partnership associates, data specialists, and customer success roles

• Panorama Education: Actively recruits educators for their remote team

Day in the Life Comparison

Understanding the daily reality of both roles helps inform the transition decision:

Teaching vs Customer Success: A Day-in-the-Life Comparison showing the transition from fixed classroom schedules to flexible corporate hours, in-person to virtual management, and structured salary to performance-based compensation.

To understand the specific skills that make teachers excel in customer success, explore my detailed guide on transferable teaching skills in CSM roles.

Essential Steps for Success

Skill Development

• Focus on business analysis capabilities

• Enhance project management expertise

• Develop proficiency with customer success software tools

Learn more about developing these skills in my in-depth analysis of teacher-to-CSM transitions.

See more about the essential capabilities in this Customer Success Manager Skills Guide.

Networking Strategy

• Connect with curriculum leads and TOSAs

• Leverage LinkedIn to identify companies where former colleagues work

• Attend industry events and webinars

Successful Transition Strategies

For those starting from scratch, my Break Into Customer Success Without Experience Guide provides a step-by-step roadmap.

Start with EdTech

• Target companies whose products you've used in the classroom

• Leverage your firsthand experience with educational technology

• Understand educator needs from both sides

Explore the latest tools transforming the industry in my Best Customer Success Platforms overview.

Alternative Entry Points

• Consider Customer Success Specialist or Associate roles

• Explore SDR (Sales Development Representative) positions as stepping stones

• Look for Implementation Specialist roles that value teaching experience

Real Success Stories

Teachers who have successfully transitioned report improved work-life balance and career satisfaction.

Many find that their classroom management, communication, and problem-solving skills transfer perfectly to customer success roles.

The path may be challenging, but success stories across various sectors show that the transition is achievable with persistence and strategic planning.

With EdTech companies actively seeking former educators and clear compensation advantages, 2025 might be your year to make the move.

For more insights on making this career change, read my collection of Customer Success Career Transition Stories.

And That’s It

Your teaching experience isn't just relevant - it's valuable.

The skills you've developed managing classrooms, communicating with diverse stakeholders, and driving student success directly translate to customer success roles.

The key is presenting these skills in business terms and targeting companies that recognize their value.

As the customer success field continues to evolve fast in 2025, with 52% of CS teams investing in AI and 94% emphasizing cross-functional collaboration, staying informed about industry trends is key for a successful transition.

For more strategic insights on making this career move, including a detailed skills analysis and sample cover letter, read my guide 'From Teacher to Customer Success: Skills That Shine in CSM Roles'

Note: All salary data is based on current U.S. market averages and may vary by location and experience level.