Customer Success Specialist - Chicago

Job Title: Customer Success Specialist (Entry-Level)

Location: Chicago, Hybrid (3 days in office)
Job Type: Full-time
Salary: $60,000–$66,000 OTE

👋 About the Role

This is an entry-level role designed for someone early in their career — maybe this is your first role in sales, partnerships, or account management. You don’t need years of experience — what matters most is your mindset: curiosity, resilience, and a genuine interest in helping others.

You’ll sit at the heart of what we do: building relationships with schools and supporting educators to find meaningful work. It’s a fast-paced, people-focused role where no two days are the same. One moment you might be helping a school solve a staffing challenge, and the next you’re coaching an educator to succeed in their role.

If you’re excited by the idea of learning quickly, taking ownership early, and making a real-world impact in education — this could be a great fit.

👋 About Zen Educate

Zen Educate is a technology company that matches schools with temporary educator staff. Our mission is to change the world of education recruitment.

Schools spend over $9bn a year on temporary educators, with over $2bn going to agency fees — money that could be better spent in classrooms. By building a smarter platform, we help schools save money while ensuring educators earn more.

We care deeply about the impact we make. We go the extra mile to find, onboard, match, and support educators who truly care about students. Every day, we’re working to improve access to quality education.

We’re a high-growth startup that recently raised $37M in Series B funding and are expanding rapidly across the UK and US. That means lots of opportunity to learn, grow, and shape your career.

🏗️ What You’ll Be Doing

Supporting School Partnerships

• Build and manage relationships with schools and districts

• Help schools find the right educators quickly and efficiently

• Identify opportunities to grow partnerships and introduce new services

• Act as a reliable, responsive point of contact for school stakeholders

• Share feedback and insights with internal teams to improve our product

Supporting Educators

• Help newly onboarded educators find their first roles quickly

• Check in regularly with educators to ensure they’re happy and supported

• Troubleshoot challenges and find solutions when issues arise

• Coach educators and guide them through training to improve performance

Day-to-Day Impact

• Balance relationship-building with fast-paced problem solving

• Work across both schools and educators to make great matches happen

• Take ownership of your portfolio and grow it over time

🧠 What We’re Looking For

We’re less focused on what you’ve done before, and more on how you think and approach work.

Mindset

• You’re eager to learn and open to feedback

• You’re resilient and don’t get discouraged by challenges

• You take initiative and aren’t afraid to figure things out

• You care about people and enjoy helping others succeed

• You’re positive, collaborative, and a great teammate

Skills & Experience

• Strong communication and interpersonal skills

• Organized and able to manage multiple priorities

• Interest in education or social impact is a big plus

• Any experience in sales, customer service, education, or recruitment is helpful — but not required

🌱 Growth & Development

This role is designed as a launchpad for your career.

You’ll gain hands-on experience in:

• Account management and relationship building

• Sales and commercial thinking

• Problem solving in a fast-moving environment

We invest heavily in learning and development and provide regular feedback to help you grow quickly.

🤝 Team & Culture

We’re a collaborative, mission-driven team that genuinely cares about what we’re building.

• We celebrate wins together and support each other through challenges

• We value curiosity, ownership, and action over perfection

• We’re building systems and processes — not just maintaining them

• We believe in doing work that has a real, positive impact

You’ll be joining a team with diverse backgrounds — including former educators, career changers, and people starting their first roles.

⭐ Benefits

• Competitive salary commission (OTE)

• 18 days PTO (15 flexible 3 for Christmas closure)

• Health insurance

• Quarterly social events

• A supportive, tight-knit team

• Meaningful work you can be proud of

⚡ Hiring Process

• Intro call with Talent Team

• Role-focused interview

• Final conversation (values & team fit)

We aim to move quickly and keep you informed throughout the interview process.

🚀 Ready to Apply

If you’ve read this far and feel excited — even if you’re not 100% sure you meet every requirement — we’d love to hear from you.

We welcome applicants from all backgrounds and experiences. At Zen, we’re committed to building an inclusive environment where everyone feels valued, heard, and supported.

If you need any adjustments during the interview process, just let us know.