Training Specialist - Independent Contractor

Position Overview: We are seeking a Training Specialist I to help ensure our customers have a superior experience every time they interact with Diligent’s suite of products and services. This role focuses on delivering high-quality initial training following purchase, as well as ongoing coaching for users at all levels throughout their relationship with Diligent. As a member of the Training team, you will join a group that is passionate about living Diligent’s corporate values and fostering a friendly, positive, and customer-centric culture. The team is committed to helping customers succeed by delivering memorable training experiences that drive product adoption, customer satisfaction, and referrals. Key Responsibilities Deliver engaging training sessions that drive product adoption and achieve high customer satisfaction (CSAT) scores. Manage and deliver product training via virtual conferencing tools (e.g. Zoom, Microsoft Teams) and webinar platforms (e.g. BigMarker). Facilitate individual, group, webinar, and in-person training sessions with confidence and professionalism. Create training resources and learning content using professional tools (e.g. iSpring, Iorad). Develop clear, customer-facing training videos to support product education. Observe training interactions and identify opportunities that may lead to potential lead generation, as appropriate. Accurately log all training activities in internal systems for reporting and tracking purpose. Handle training-related client requests and queries, along with other administrative tasks as required. Travel occasionally for professional development, customer workshops, or internal meetings. Required Experience/Skills 0–3 years of relevant professional experience. Strong planning, organization, and time management skills. Customer-focused mindset with a passion for delivering excellent service. Effective interpersonal, communication, and presentation skills, with the ability to be both assertive and respectful. High level of energy, professionalism, and resourcefulness. Ability to remain calm, think on their feet, and respond positively in unexpected situations. Preferred Experience/Skills Experience creating learning content or training materials (eg. Using iSpring, Creating IORADs, Video editing etc). This is a fixed-term independent contractor opportunity supporting the team through the end of 2026. The selected contractor will provide services and will invoice directly on a monthly basis. Compensation will be paid as a fixed monthly professional fee against invoice. This is a professional services engagement and is not eligible for company-sponsored benefits. While the assignment is currently expected to conclude on December 31, 2026, there may be an opportunity for extension based on business needs. About Us Diligent is the AI leader in governance, risk and compliance (GRC) SaaS solutions, helping more than 1 million users and 700,000 board members to clarify risk and elevate governance. The Diligent One Platform gives practitioners, the C-Suite and the board a consolidated view of their entire GRC practice so they can more effectively manage risk, build greater resilience and make better decisions, faster. At Diligent, we're building the future with people who think boldly and move fast. Whether you're designing systems that leverage large language models or part of a team reimaging workflows with AI, you'll help us unlock entirely new ways of working and thinking. Curiosity is in our DNA, we look for individuals willing to ask the big questions and experiment fearlessly - those who embrace change not as a challenge, but as an opportunity. The future belongs to those who keep learning, and we are building it together. At Diligent, you’re not just building the future - you’re an agent of positive change, joining a global community on a mission to make an impact. Learn more at diligent.com or follow us on LinkedIn and Facebook What Diligent Offers You Creativity is ing…