Sr. Trainer - Customer Success Operations

Human Interest is on a mission to ensure that people in all lines of work have access to retirement benefits. More than half of all working Americans are not saving enough for their future. Too often, it’s because they are employed by a company that doesn’t offer a retirement plan. Human Interest is changing that by making it affordable and accessible for small and medium-sized businesses to offer employees a path to financial independence through retirement savings. We’re a high-growth fintech company changing the retirement industry. We are backed by a number of investors. This includes funding from Marshall Wace and Baillie Gifford, as well as top investors such as BlackRock , TPG (The Rise Fund) , SoftBank, Glynn Capital , NewView Capital, USVP, Wing, Uncork, and more. About the role As Human Interest scales for its next phase of significant growth, we're looking for an imaginative, adaptable, and people-centric Sr. Trainer, CSO Enablement . This pivotal role exists to create meaningful, practical, and scalable learning experiences that directly empower our Customer Success organization. You'll be instrumental in developing and delivering critical training programs, collaborating extensively with Revenue leaders, Partner Marketing, and other Enablement team members. Acting as a thought leader, you'll ensure a seamless experience, always keeping the learner’s journey and experience as your guiding light. This is a hands-on role where you'll roll up your sleeves, default to action, and drive strategies that amplify Human Interest's mission to make retirement accessible to all. Given our rapid pace (i.e., 24,791 mph), you'll need to thrive amidst constant change while consistently delivering successful, high-quality outcomes. This role reports to the Sr. Manager, CSO Revenue Enablement. What you get to do every day Training & Facilitation Excellence • Lead and facilitate dynamic, instructor-led Onboarding, Upskill, and Continuing Education courses for our Customer Success Support Associate and Client Relationship Manager programs. You'll expertly guide employees through self-led learning content, taking full ownership of impactful sessions from start to finish, with additional programs to be supported in the future. • Maintain a deep, working knowledge across multiple functional areas, delivering training that seamlessly integrates complex processes often opaque to single-discipline practitioners. • Elevate advanced learners by addressing outcomes that demand significant prerequisite skills. You'll prepare team members who have already excelled at the entry-level, engaging them with content that not only recognizes but actively capitalizes on their shared experiences and veteran insights. • Leverage learning theory to ensure that all methods are implemented to give any and all training experiences and participants the opportunity to continue to grow their knowledge and development. Recognition of how adult professionals learn is paramount to the success of programs and the business. Impact Measurement & Continuous Improvement • Evaluate trainee performance and provide precise, actionable feedback to managers. You'll establish clear criteria for successful training completion and conduct robust assessments to effectively measure employee progress. • Independently drive the creation of innovative training processes and materials, collaborating extensively with subject matter experts to ensure all content is meticulously aligned with critical business objectives. • Proactively review and refine training content at regular intervals, ensuring absolute accuracy and currency. You'll swiftly implement necessary updates across both instructor-led and e-learning materials. Drive Team Success and Values • Prioritize colle