Enablement Specialist II

About Oversight

Oversight is the world's leading provider of AI-based spend management and risk mitigation solutions for large enterprises. Based in Atlanta, GA, Oversight works with many of the world's most innovative companies and government agencies to digitally transform their spend audit and financial control processes.

Oversight's AI-powered platform works across customers' financial systems to continuously monitor and analyze spend transactions for fraud, waste, and misuse. With a consolidated, consistent view of risk across the enterprise, customers can prevent financial loss, strengthen compliance, and improve operational efficiency. Learn More.

Position Overview: Job Purpose

The Enablement Specialist II (ES II) is a client-facing, consultative enablement role responsible for driving successful onboarding, adoption, and operationalization of Oversight solutions during implementation engagements.

The ES II operates with increasing independence and is expected to lead core enablement activities for assigned clients while partnering closely with Project Management, Technical Delivery, Client Success, and Support throughout the onboarding lifecycle. This role balances client-specific needs with established enablement standards and best practices to deliver scalable, sustainable outcomes.

The ES II is responsible for configuring and refining Oversight analytics, guiding clients through enablement and training activities, and helping clients operationalize Oversight workflows in alignment with their audit objectives, policies, and reporting needs. The ES II will also serve as a contributor to internal and external documentation.

Candidate Profile

The ideal ES II candidate has experience independently supporting client onboarding or implementation engagements and is comfortable operating in a consultative, client-facing environment with moderate autonomy.

Experience

• 2-5 years of experience in client-facing implementation, onboarding, consulting, enablement, client success, or professional services roles
• Experience independently managing defined portions of client engagements, including trainings, configuration activities, and follow-up actions
• Comfortable facilitating client meetings, trainings, and working sessions with professionalism and confidence
• Experience balancing multiple active projects, timelines, and client priorities simultaneously
• Experience documenting requirements, configurations, refinements, and operational decisions in structured systems or tools
• Familiarity working cross-functionally with technical, project management, support, or customer success teams
• Experience identifying process improvement opportunities or recommending operational refinements

This role is intended for candidates who can operate independently within established frameworks and who are ready to take ownership of core enablement responsibilities with limited day-to-day direction. Because the role supports global clients across multiple regions, candidates should also be comfortable working flexibly to accommodate client meeting and training schedules when needed.

Core Responsibilities

• Lead onboarding and enablement activities for assigned client engagements
• Tune Oversight analytics to align with client policy requirements
• Collaborate with Project Management on onboarding timelines and delivery adjustments
• Partner with Technical Delivery on system refinements and investigations
• Collaborate with Client Success on adoption progress and client risks
• Coordinate with Support on implementation details and post-go-live transitions
• Create and maintain Email Templates, Reason Codes, and related client configurations
• Record and maintain system changes through Implementation Workbooks and Jira OBX tickets
• Train clients on Oversight analytics, Workbench workflows, Dashboards, and Exception Resolution processes
• Guide clients on analytics functionality, refinement options, and operational best practices
• Review client utilization and identify adoption and workflow improvement opportunities
• Identify system, process, and enablement improvement opportunities
• Maintain current knowledge of Oversight products, analytics, tools, and processes
• Communicate proactively and collaborate effectively across internal teams and client stakeholders
• Contribute to internal and client-facing documentation, training materials, and process improvements
• Share client feedback and enhancement opportunities with Product Management

Core Skills

• Strong client-facing communication, presentation, and consultative skills
• Ability to facilitate trainings, lead working sessions, and communicate complex concepts in a clear and practical way
• Strong organizational and time management skills with the ability to manage multiple projects, priorities, and deadlines simultaneously
• Analytical and detail-oriented with the ability to identify trends, risks, process gaps, and operational improvement opportunities
• Ability to think critically, solve problems independently, and make sound decisions in client-facing situations
• Experience working in client onboarding, implementations, enablement, consulting, professional services, or similar client delivery environments
• Ability to build professional relationships and collaborate effectively with clients and cross-functional internal teams
• Comfortable working within structured processes, documentation standards, and ticketing or workflow management systems
• Strong written documentation skills with experience creating or maintaining process documentation, training materials, or client-facing content
• Adaptable and comfortable working in fast-paced environments with evolving client needs and priorities

Success Metrics

• Client onboarding progress and adoption outcomes
• Quality, consistency, and timeliness of enablement delivery
• Accuracy and completeness of system configurations and documentation
• Effective collaboration with internal stakeholders and cross-functional teams
• Client feedback, engagement, and onboarding readiness indicators
• Adherence to team processes, standards, and operational expectations