Enablement Specialist

OSG•Carol Stream, IL

5d•$58,000 - $70,000•Onsite

About The Position

OSG is seeking an early-career Enablement Specialist to join its Revenue Operations & Enablement team. The role focuses on building self-service learning for the sales organization through on-screen digital guidance and self-service training materials, reducing reliance on repetitive live onboarding sessions and demos. It is a growth-track opportunity to develop expertise in enablement and digital adoption. The Enablement Specialist will create and maintain guidance for core sales tools, develop onboarding resources, and organize a central library of current enablement content. The role works with Enablement, CRM, and Sales leadership to identify workflow challenges, track content adoption and effectiveness, and improve materials based on results. It may also support broader enablement projects, including training curriculum and certification tracking, as capacity allows. The position is onsite four days per week at OSG’s Carol Stream, Illinois facility.

Requirements

Bachelor’s degree in Business, Education, Communications, or a related field, or equivalent practical experience.
0–1 years of experience; candidates from adjacent fields such as training, HR, or customer support, or with relevant coursework or internship experience, are encouraged to apply.
Comfort learning new software tools quickly and translating workflows into simple guided steps.
Strong written communication skills; the role centers on creating content, not only delivering it.
Self-starter able to work independently from a content backlog.

Nice To Haves

Experience with Claude or similar AI assistants (strongly preferred).
Familiarity with digital adoption or guidance platforms such as Whatfix, WalkMe, or Pendo; training on these tools will be provided.

Responsibilities

Build and maintain on-screen guidance content for core sales tools, including CRM, quoting, and deal desk systems.
Develop self-service onboarding materials so new sales representatives can ramp without one-on-one walkthroughs.
Maintain and organize a central library of enablement content, keeping materials current as tools and processes change.
Reduce the Enablement team’s repetitive live demo and onboarding workload.
Partner with Enablement, CRM, and Sales leadership to identify where representatives get stuck and create guided content to address those gaps.
Track usage, completion, and ramp-time impact of guidance content, and iterate based on findings.
Support broader enablement projects, such as training curriculum and certification tracking, as capacity allows.