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 collective success by consistently aligning individual contributions with overarching team objectives.
• Strategically contribute to sustained growth by focusing on long-term impact rather than immediate, short-term solutions.
• Execute all tasks with attention to detail, demonstrating an unwavering commitment to delivering high-quality content, resulting in minimized spelling, grammar, design, or communication errors.
• Achieve superior training outcomes, consistently securing 80% or higher in all formal trainer performance observations.
• Foster a culture of seamless collaboration by effectively communicating and partnering with all enablement team members to achieve our collective goals. 
• Champion organizational directives by actively demonstrating unwavering support for company-wide initiatives and key stakeholder strategies.

Strategic Partnership & Cultural Advocacy

• Serve as a pivotal ambassador for Human Interest and Enablement, warmly welcoming new team members and ensuring they experience a profoundly successful onboarding journey in their roles. You should carry this into all training environments you are responsible for or take part in.
• Partner strategically with operational leadership to meticulously review training needs and pinpoint knowledge gaps. You'll then develop comprehensive plans to address these, closing the loop with data-driven insights.

What You'll Accomplish

• Cement our training culture by unequivocally demonstrating the inherent value of the training function beyond the virtual classroom. You'll inspire unwavering trust in a trainer’s ability to play an integral role in driving significant improvements across the entire organization.
• Deliver top-tier training programs that not only deeply engage learners but genuinely excite them about their roles, empowering them to achieve unparalleled success. Your efforts will consistently yield top-tier feedback from both learners and leadership teams.
• Strategically increase efficiency by proactively identifying areas ripe for process improvement and collaborating seamlessly with appropriate stakeholders to optimize key policies, processes, and procedures.

What you bring to the role

• A strong foundation: You ideally have a BA degree or equivalent practical experience.
• A passion for enablement: You bring 5+ years of proven experience in teaching, training, or a closely related field, demonstrating a true knack for developing and elevating others.
• SaaS Savvy: You have a clear understanding of SaaS business motions and the e