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Edtech Onboarding Jobs in Chicago, IL (NOW HIRING)

Senior Academic Advisor

Chicago, IL · On-site

$140K - $141K/yr

As one of the fastest-growing edtech firms in the world, we are backed by some of the leading ... Support onboarding and customer success for newly enrolled students to ensure a strong start and ...

Customer Success Manager

Chicago, IL · Remote

$85K - $95K/yr

This is execution at scale: technical onboarding, staff training, troubleshooting, adoption ... Experience in EdTech, education, or healthcare partnerships, product support, and enablement * K-12 ...

New

We have recently raised our Series B funding of $37mil, the largest round in European EdTech this ... Guide candidates through onboarding: Help candidates navigate our screening and document collection ...

We have recently raised our Series B funding of $37mil, the largest round in European EdTech this ... Guide candidates through onboarding: Help candidates navigate our screening and document collection ...

Head of Marketing

Chicago, IL · On-site

$100 - $150/hr

... onboarding → release awareness → feature adoption → expansion → renewal Brand & Thought ... Vertical SaaS, EdTech, or higher-education-adjacent background is a strong plus. * Leadership ...

Edtech Onboarding information

See Chicago, IL salary details

$13

$26

$49

How much do edtech onboarding jobs pay per hour?

As of Sep 5, 2026, the average hourly pay for edtech onboarding in Chicago, IL is $26.73, according to ZipRecruiter salary data. Most workers in this role earn between $19.57 and $29.95 per hour, depending on experience, location, and employer.

What is Edtech onboarding?

Edtech Onboarding refers to the process of introducing and training educators, students, or administrators on how to effectively use educational technology platforms and tools. This process typically includes initial account setup, walkthroughs of key features, best practices for classroom integration, and ongoing support. Effective onboarding helps ensure that users can confidently use the technology to enhance teaching and learning outcomes. It often involves live training sessions, tutorials, documentation, and access to support resources.

What are some common challenges faced during the Edtech onboarding process, and how can new hires effectively navigate them?

One common challenge in Edtech onboarding is adapting to rapidly evolving technologies and learning platforms, which may differ from traditional educational tools. New hires often need to quickly grasp the unique features of the company's product and understand both the technical aspects and pedagogical goals. Collaborating with cross-functional teams—such as product managers, educators, and customer success reps—is essential for a smooth onboarding experience. Proactively seeking feedback, participating in training sessions, and leveraging mentorship programs can help new hires overcome these challenges and integrate successfully into the team.

What are the key skills and qualifications needed to thrive as an Edtech Onboarding specialist, and why are they important?

To thrive as an Edtech Onboarding Specialist, you need expertise in educational technology, strong training or instructional skills, and a background in education or customer success. Familiarity with learning management systems (LMS), digital classroom tools, and onboarding or CRM platforms is typically required. Outstanding communication, patience, and problem-solving abilities help build rapport with educators and ensure a smooth transition to new tools. These skills are crucial for facilitating effective adoption, minimizing user frustration, and driving long-term engagement with edtech solutions.

What is the difference between Edtech Onboarding vs Edtech Customer Support?

AspectEdtech OnboardingEdtech Customer Support
Required CredentialsTypically a background in education, training, or instructional design; often a bachelor's degreeCustomer service experience, communication skills, sometimes technical knowledge
Work EnvironmentPrimarily training sessions, workshops, and one-on-one onboarding with new clients or usersHelp desks, support tickets, live chat, and phone support for existing users
Employer & Industry UsageUsed by edtech companies to ensure clients understand platform featuresUsed to resolve user issues, troubleshoot, and maintain customer satisfaction

While Edtech Onboarding focuses on guiding new users through platform features and training, Edtech Customer Support handles ongoing user issues and technical troubleshooting. Both roles are essential in the edtech industry but serve different stages of the user journey.

What are popular job titles related to Edtech Onboarding jobs in Chicago, IL?

For Edtech Onboarding jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Edtech Onboarding jobs in Chicago, IL look for?

The top searched job categories for Edtech Onboarding jobs in Chicago, IL are:

Infographic showing various Edtech Onboarding job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 79% Full Time, 14% Part Time, and 6% Contract. Highlights an 89% Physical, 3% Hybrid, and 8% Remote job distribution, with an average salary of $55,596 per year, or $26.7 per hour.

Sales Enablement Specialist

Inspira Education

Chicago, IL

Full-time

Medical, Dental, Vision, Retirement, PTO

Posted 6 days ago


Key responsibilities

  • Design, build, and improve onboarding programs to accelerate new-hire ramp time.

  • Develop ongoing training programs to enhance product knowledge, consultative selling, objection handling, and customer experience.

  • Partner with cross-functional teams to translate strategy into execution, support product launches, and create scalable sales enablement programs.


Job description

About Inspira Education

Inspira Education Group is one of the fastest-growing edtech startups in the US. We started with a simple mission to democratize access to high-quality coaching so that every student in the world has an equal opportunity to access the best opportunities. 

As the world's leading network of top admissions coaches in medical, legal, business, and college studies, we're building software and services in one place—disrupting long-entrenched application processes with products and experiences that strive to provide an equal platform for candidates from diverse backgrounds worldwide. 

As one of the fastest-growing edtech firms in the world, we are backed by some of the leading venture capital firms and investors in the world, including Zeev Ventures, Quiet Capital, Craft Ventures and Jeff Fluhr (Founder of Stubhub).

About the Role

We're looking for a strategic and collaborative Sales Enablement Specialist to help scale our go-to-market organization. In this role, you'll partner across Sales, Product, Product Marketing, Revenue Operations, Customer Experience, Recruiting, and Learning & Development to ensure our customer-facing teams have the knowledge, tools, processes, and content they need to deliver an exceptional customer experience and drive business results.

You'll serve as the connective tissue across our GTM organization—translating strategy into execution, identifying performance gaps, enabling successful product launches, and creating scalable programs that improve sales effectiveness and customer outcomes.

If you enjoy solving sales challenges, influencing cross-functional teams, and building programs that have measurable impact, we'd love to meet you.

 What You'll DoSales Enablement & Training
  • Design, build, and continuously improve onboarding programs to accelerate new-hire ramp time.
  • Develop ongoing training programs that strengthen product knowledge, consultative selling, objection handling, and customer experience.
  • Create certifications, learning paths, coaching resources, and sales enablement programs.
  • Analyze sales performance trends and identify opportunities for targeted enablement initiatives.
Data & Feedback Loop
  • Analyze conversion, win/loss, and retention data to identify what's working and feed it back into training
  • Review call recordings and customer interactions to surface best practices from top performers and turn them into repeatable playbooks
  • Track and report on enablement-specific metrics and their downstream impact on conversion or win rate
Cross-Functional Partnership
  • Partner with Product Marketing to translate positioning, messaging, and competitive insights into practical sales playbooks, talk tracks, FAQs, and customer-facing resources.
  • Collaborate with Product Management to prepare customer-facing teams for product launches by developing training, enablement content, and readiness plans.
  • Work closely with Marketing to ensure campaign messaging is consistently reflected throughout the customer journey.
  • Partner with Revenue Operations to support CRM adoption, process improvements, sales workflows, and operational readiness.
  • Collaborate with Customer Experience and Customer Success teams to improve onboarding, retention, upsell, and support experiences.
  • Gather frontline feedback and communicate customer insights back to Product, Marketing, and Sales Leadership to continuously improve our GTM strategy.
Content & Communication
  • Create and refine high-converting playbooks, call scripts, objection-handling guides, and cross-sell/upsell matrices for the sales team.
  • Own the organization and maintenance of sales enablement content, including playbooks, product documentation, competitive battle cards, sales presentations, and knowledge resources.
  • Ensure customer-facing teams have easy access to current, accurate, and actionable enablement materials.
  • Package customer proof points, case studies, and FAQs into reusable assets teams can pull from in the moment
  • Develop scalable communication plans for product launches, process updates, and organizational changes.
Tools & Process
  • Own or co-own enablement tooling (e.g., CRM/helpdesk macros, content/asset libraries, call recording platforms) so teams can find the right resource in seconds, not minutes
  • Partner with RevOps to keep CRM data clean and process consistent across teams
What You'll Bring
  • Prior experience carrying an individual sales quota or serving in a consultative customer-facing role (Sales, Business Development, Account Management, Customer Success, Retail Leadership, or similar). You understand firsthand what it takes to build trust with customers, navigate objections, and operate in a performance-driven environment.
  • 3+ years of experience in a customer-facing revenue role and/or Sales Enablement, Revenue Enablement, Sales Operations, Product Marketing, or a related GTM function.
  • Experience designing and scaling enablement programs that improve onboarding, sales readiness, product adoption, or customer experience.
  • Proven ability to build trusted partnerships across Sales, Product, Product Marketing, Marketing, Revenue Operations, Customer Experience, and executive leadership.
  • Excellent communication and facilitation skills, with the ability to simplify complex concepts and influence audiences ranging from frontline employees to senior leaders.
  • An analytical mindset with experience using performance metrics, customer feedback, and business insights to identify opportunities and measure the impact of enablement initiatives.
  • A builder's mentality—you enjoy creating scalable programs, playbooks, and processes that help teams perform at their best.
  • High emotional intelligence and credibility. You listen before prescribing solutions, seek to understand the realities of frontline teams, and earn trust through empathy, collaboration, and thoughtful execution.
Preferred Qualifications
  • Experience in a direct-to-consumer, retail, consumer technology, marketplace, or high-growth environment.
  • Experience supporting product launches and go-to-market initiatives across multiple customer-facing teams.
  • Familiarity with CRM platforms (Salesforce, HubSpot, or similar), learning management systems, and enablement tools such as Gong, Highspot, Seismic, WorkRamp, or similar platforms.
  • Experience coaching managers or facilitating leadership development programs.
Success in This Role

After your first 60-days, you will have:

  • Built scalable onboarding and ongoing enablement programs that improve sales readiness and consistency.
  • Successfully enabled multiple product launches across customer-facing teams.
  • Established trusted partnerships across Sales, Product, Marketing, Revenue Operations, and Customer Experience.
  • Increased adoption of key sales processes, tools, and messaging.
  • Demonstrated measurable improvements in ramp time, productivity, customer experience, or sales effectiveness.
  • Become a strategic partner who helps connect business strategy with frontline execution.
Why This Role Matters

Our customers experience our brand through every interaction with our teams. This role helps ensure those interactions are consistent, informed, and customer-centric. By connecting strategy with execution and enabling our teams to perform at their best, you'll play a critical role in helping us scale our business while delivering an outstanding customer experience.

 Why You'll Love Inspira
  • Amazing people with a great vision and values
  • Mission-driven team culture focused on student success
  • Your work directly impacts the lives and careers of students across the globe
  • Health, dental, and vision insurance, base plans 100% employer paid
  • Pre-tax benefits (FSA, DCFSA, HSA, Commuter)
  • Flexible paid time off (PTO) and paid holidays
  • 401(k) with company match

For more information about our company, please visit our website: Inspira Education Group.  

Inspira Education Group does not discriminate based on race, sex, color, religion, age, national origin, marital status, disability, veteran status, genetic information, sexual orientation, gender identity, or any other reason prohibited by law in providing employment opportunities and benefits.