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