Entry Level Startup Jobs in Chicago, IL (NOW HIRING)

Company Description
Education Walkthrough is a streamlined classroom observation platform for K-12 principals, instructional coaches, and district administrators. Our mobile app empowers educators to observe, document, and immediately share feedback on classroom instruction and learning. The data collected is available on our website, where educators can analyze trends, patterns, and gaps in teaching practices-insights that are essential for administrators planning professional development workshops aimed at enhancing teacher effectiveness and student learning outcomes.
Founded in 2019 in Chicago by a serial entrepreneur, Education Walkthrough has grown organically to support over 500 districts across the United States and is now utilized in more than 10 countries worldwide.
As our team grows, we are seeking exceptional individuals committed to our vision. At Education Walkthrough, we are driven by the conviction that greatness stems from attention to the smallest details. We believe that by empowering teachers to enhance their instructional techniques, we can fundamentally elevate the quality of education for millions of students worldwide.
Watch this quick video to learn more about Education Walkthrough. (https://www.youtube.com/watch?v=0k58eC0OgKI )
Does our company resonate with you? If so, reach out, even if your profile doesn't match our current openings. We're always on the lookout for outstanding people to join our team.
Job Description
The Role
You'll manage a portfolio of customers with one primary objective: delight them. You'll be a trusted partner to school and district leaders, staying in regular contact to help them get real value from the Education Walkthrough platform. You'll own onboarding, training, and ongoing support; spot opportunities to deepen their success; and carry their feedback back to our product team.
This is not a role where you'll be handed a book of problems and asked to bring your own system. We have a proven approach and a team that will train you into it. What matters most is that you build genuine relationships, care about the outcome, and get better every week.
Qualifications
Key Responsibilities:

• Own customer onboarding, training, and ongoing support so customers fully adopt and benefit from the platform.
• Stay proactively in touch at the moments that matter, catching small issues (usage gaps, upcoming deadlines, role changes) before they become big ones, rather than waiting for tickets.
• Build real relationships with school and district leaders, and turn moments of value into referrals and introductions.
• Manage renewals and identify natural expansion opportunities within your accounts.
• Represent the voice of the customer internally to help improve the product.
• Create and maintain clear support documentation and enablement resources so customers have self-service help at their fingertips.
• Participate actively in daily account check-ins and keep clear, useful records of every account.

Skills & Experience:
You don't need years of customer success experience or a playbook of your own. We can teach the product, the process, and the tools. What we can't teach is who you are, and that's what we're hiring for:

• A genuinely good person. Kind, warm, someone leaders trust and enjoy talking to, who can move a conversation past the purely transactional and connect with educators as people.
• A proactive problem-solver who's detail-oriented and thinks a step ahead.
• Loves data and making data-driven decisions. You enjoy looking at spreadsheets, asking questions, thinking strategically about issues, and building a case for your decision.
• Growth-minded. You naturally look for ways to add value, and you're comfortable asking for referrals and introductions once a customer feels the impact.
• A strong communicator, in writing, on the phone, and on screen.
• Coachable and eager to learn. You want to master our product and our way of doing things, and you get sharper with every account.
• Comfortable with technology and willing to learn our stack (HubSpot, FullStory, Slack, etc.). Previous experience with a CRM system is important.
• Curious about AI and comfortable putting it to work. We build AI into our product and use it across our own workflows. You do not need to be an expert but you do need to have played with it and open to leaning in.
• 2+ years in a role where relationships and follow-through mattered. Could be from teaching, account management, client services, sales, coaching, hospitality, etc.

Nice to have, but not required: classroom teaching or school administration experience (a big plus for building instant rapport with educators), prior customer-facing or SaaS experience, and hands-on time with a CRM like HubSpot.
Additional Information
What We Offer:

• A chance to be part of a rapidly growing startup with a global impact on education.
• Competitive salary and benefits package.
  • Salary range: $60,000-$70,000, depending on experience and location. This is an entry-level Customer Success role with a clear path to grow into a senior seat as you take on more of the customer lifecycle.
• A collaborative, innovative atmosphere with great potential for personal and professional growth.

How to Apply:
We want the real you, not a polished template. Please submit:

• Your resume + cover letter with the following:
  • A short note (200-300 words, in your own words) about a relationship you built, at work or in life, where your follow-through changed the outcome. Tell us what actually happened: the person, the situation, what you did.
  • A short note about if and how you used AI to help with any part of this application. We use Ai every day here. We are not testing whether you use it, we're testing whether you are honest about it.

Applications without the note and the video may not be reviewed.
Videos To Watch
https://www.youtube.com/watch?v=0k58eC0OgKI