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Software Trainer and Instructional Designer

Position Overview

The Software Trainer and Instructional Designer is responsible for the creation and execution of a comprehensive and integrated learning program to educate customers and staff on the use, configuration and maintenance of the Oversight software suite and related products as delivered through channel partnerships. 

In this role, you will be accountable for the establishment and the management of a learning curriculum including designing, developing and delivering experiential learning opportunities through instructional materials, training courses, online learning and multimedia technologies. This role collaborates with business leaders to identify and create action plans to address gaps in learning. The position will leverage the knowledge and experience of subject matter experts throughout the organization. It will influence team members across functional, geographical and divisional boundaries.



  • Development and delivery of a curriculum of training courses in the use and maintenance of the Oversight software and related products and services delivered through channel partnerships

  • Development and ongoing upkeep of training materials including lesson plans, learning objectives, functional and role guides and relevant exercises

  • Develop a schedule of individual and group training events. Maintain rosters and attendance records

  • Maintain a working, current knowledge of the Oversight software suite and a general familiarity with the business domains for which it is used

  • Compile and publish training metrics

  • Monitor and improve Oversight training effectiveness through student evaluations, benchmarking and measurable business results

  • Continuously innovate, leveraging technology, best practices and other available assets 

  • Coordinate and schedule time and/or travel itineraries as needed for remote training events and assignments 

  • Keep up-to-date with changes to company products, tools and processes 

  • Communicate effectively and maintain a proactive, positive relationship with all departments within the company, notably including Sales, Marketing, Client Support and Client Success & Delivery 

  • Support and assist the Product Development organization by sharing customer and individual feature enhancement ideas and suggestions or participating in Product development and testing 

  •  Assist with mentoring and training new employees 

  • Occasionally present product knowledge or domain expertise via speaking, training or sales environments including customer conferences, trade shows, conventions or public speaking engagements 

  • Assist with a variety of other special assignments to support Learning and Development efforts across the organization 


Experience Required

  • At least 5 years teaching experience as a corporate trainer or a teacher in higher education

  • Software training experience or teaching experience in a technology field

  • Experience in designing and writing course materials 

  • Competency in common business applications including the Microsoft Office suite

  • Demonstrated ability in instructional design and adult learning

  • Preferred: Experience managing client-facing projects

  • Preferred: Experience with creating/editing training videos

  • Preferred: Experience with Learning Management Systems


Education/Professional Qualifications

  • Strongly preferred: Bachelors or equivalent 4-year college degree

  • Preferred: Degree in teaching, Masters or certification in the teaching field

  • Preferred Concentration: Adult Education 

  • Preferred: Formal project management training, certification or experience

Candidate Characteristics

  • Candidate must have excellent communication, presentation and interpersonal skills

  • Candidate must have strong presentation, interpersonal and consultative skills

  •  Candidate must be a self-starter able to work in a fast-paced dynamic environment

  • Candidate must possess initiative to produce improvement initiatives both internally and with clients 

  • Candidate must be organized and analytical, with the ability to eliminate obstacles through creative and adaptive approaches 

  • Candidate should be naturally curious, willingness to ask questions to identify the “Why”

  • Candidate should have a patient and friendly approach to teaching 

  • Candidate must be able to read visual cues from classroom situations and adjust content as necessary 

  • Candidate must be fully committed to conducting business with the utmost integrity and in full compliance with policies, procedures and legal requirements

  • Candidate must be fully committed to conducting business with the utmost integrity and in full compliance with policies, procedures and legal requirements


If this sounds like a good fit for you, please submit your resume to recruiter@oversightsystems.com.


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 our customers’ financial systems to continuously monitor and analyze all spend transactions for fraud, waste, and misuse. With a consolidated, consistent view of risk across their enterprise, customers can prevent financial loss and optimize spend while strengthening the controls that improve compliance. Learn More.


Oversight is an equal opportunity employer.

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