Enablement Specialist

OSG is a global provider of leading customer engagement and payment solutions. We help clients integrate critical customer interactions to optimize working capital and drive profitable business growth. Our solutions connect the entire customer experience by aligning transactional, payment, and marketing touchpoints for simplified operations and smarter engagement.

Powered by innovative technology and data-driven insights, we build tailored, digital-first strategies for a range of industries. Our clients benefit from a partnership that values simplicity, security, and connectivity, for today and for tomorrow's innovation.

We are looking for an Enablement Specialist to join our Revenue Operations & Enablement team and help build self-service learning for our sales organization. You will create on-screen digital guidance content (Whatfix/WalkMe-style) and self-serve training materials, reducing the team's reliance on live, repetitive onboarding sessions and demos.

This is a growth-track role. We are looking for someone early in their career who wants to build deep enablement and digital-adoption expertise over time.

Job Details

• In-app guidance: Build and maintain on-screen guidance content for core sales tools, including CRM, quoting, and deal desk systems.
• 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, keeping materials current as tools and processes change.
• Reducing live demand: Reduce the repetitive live demo and onboarding load currently carried by the Enablement team.
• Gap identification: Partner with Enablement, CRM, and Sales leadership to find where reps get stuck and turn those gaps into guided content.
• Adoption tracking: Track usage, completion, and ramp-time impact of guidance content, and iterate based on findings.
• Project support: Support broader enablement projects, such as training curriculum and certification tracking, as capacity allows.

Required Qualifications

• 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.
• Comfortable learning new software tools quickly and translating workflows into simple guided steps.
• Strong written communication skills. This role centers on creating content, not only delivering it.
• Self-starter who can work independently from a content backlog.

Preferred Qualifications

• 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.

What Success Looks Like in the First 6 Months

• Fewer ad hoc onboarding requests to the Enablement team.
• A working library of self-service guidance for the 5-10 highest-friction workflows.
• Baseline usage and effectiveness data established for future iteration.
• Positive feedback from new hires on their ramp experience.

Location

This is an onsite 4-days a week in office position based at OSG's Carol Stream, IL facility.

Benefits

• Paid time off (PTO)
• Medical, dental, and vision plans
• Employee assistance program
• Life insurance and long-term disability (LTD) plans
• Supplemental life insurance
• Voluntary accident and critical illness insurance
• Flexible Spending Account
• 401(k) plan

OSG offers equal employment opportunity and will not discriminate on the bases of race, religion, color, sex (including pregnancy, gender identity, and sexual orientation), parental status, national origin, age, disability, family medical history or genetic information, political affiliation, military service, or other non-merit based factors.