Enablement Specialist: Self-Service Training & Content Lead

OSG; Carol Stream (IL); On-site; USD 58,000 - 70,000; Full time

Benefits offered by this job

Paid time off

Medical, dental, and vision plans

Employee assistance program

Life insurance

Long-term disability (LTD) plans

Supplemental life insurance

Flexible Spending Account

401(k) plan

Job summary

OSG is seeking an Enablement Specialist to join the Revenue Operations & Enablement team in Carol Stream, IL. The role focuses on building self-service, Whatfix/WalkMe-style on-screen guidance and training materials to reduce live onboarding and demos.

Early in career, candidate will develop deep enablement and digital-adoption expertise while supporting core sales tools and a growing content library. Onsite 4 days a week in Carol Stream with a comprehensive benefits package.

Qualifications

• Bachelor's degree in Business, Education, Communications, or equivalent practical experience.
• 0-1 years of experience; adjacent fields encouraged.
• Comfortable learning new software tools quickly and translating workflows into simple guided steps.
• Strong written communication skills; this role centers on content creation.
• Self-starter who can work independently from a content backlog.

Responsibilities

• In-app guidance: Build on-screen guidance content for core sales tools (CRM, quoting, deal desk).
• Self-service onboarding: Develop onboarding materials so new sales reps can ramp without one-on-one walkthroughs.
• Content library: Maintain and organize a central library of enablement content, updating as tools/processes change.
• Reducing live demand: Reduce repetitive live demos and onboarding load by the Enablement team.
• Gap identification: Partner with Enablement, CRM, and Sales leadership to identify gaps and create guided content.
• Adoption tracking: Track usage, completion, and ramp-time impact of guidance content and iterate.
• Project support: Assist broader enablement projects like training curriculum and certification tracking.

Skills

Content creation

Written communication

Independent work

Self-motivation

Learning agility

Education

Bachelor's degree in Business, Education, or Communications

Tools

Whatfix

WalkMe

Pendo

Claude

Job description

OSG is seeking an Enablement Specialist to join the Revenue Operations & Enablement team in Carol Stream, IL. The role focuses on building self-service, Whatfix/WalkMe-style on-screen guidance and training materials to reduce live onboarding and demos.

Early in career, candidate will develop deep enablement and digital-adoption expertise while supporting core sales tools and a growing content library. Onsite 4 days a week in Carol Stream with a comprehensive benefits package.