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 entire customer lifecycle.
• Customer-centric mindset: You've got proven customer management skills, especially with large and complex accounts.
• Impact-driven: You have a proven track record of meeting and exceeding team objectives, constantly striving for measurable results.
• Exceptional communicator: Your written and spoken communication is top-notch, allowing you to clearly convey complex ideas.
• Collaborative spirit: You're adept at developing strong working relationships at all levels of management, both within and outside Human Interest.
• Analytical and organized: You possess top-notch organizational and analytical skills, with a keen ability to use data to inform business decisions and achieve goals.
• Agile and adaptable: You thrive in a startup and SaaS background (preferred), demonstrating comfort with rapid change and a willingness to take calculated risks.
• Tool proficiency: Experience using Salesforce, Docebo, Google Drive, and other LMS systems is a definite plus.

Why you will love working at Human Interest

Human Interest is tackling one of our country's biggest challenges - closing the retirement gap. You'll be instrumental in architecting and scaling solutions that bring financial security to employees at small and medium-sized businesses nationwide. We’ve made significant progress, but there is still growth ahead, offering you a unique opportunity to solve complex problems, drive innovation, and advance your career alongside a dedicated, mission-driven team. We value hard work and recognize that our team's contributions are key to our continued success.

Join Human Interest and make a lasting impact by shaping the future of retirement.

Our operating principles define how we work together as a team. They reflect Human Interest’s unique view on what’s important and what’s right. Documenting this core aspect of our culture helps employees make good decisions on their own. It also helps candidates considering career opportunities critically evaluate whether they will thrive at Human Interest. 

• Customer obsession: We're all about creating amazing experiences for our customers. We put their needs first and go the extra mile to make them smile.
• Long-Term Orientation: We're not just playing for today; we're building a legacy. We think big, plan strategically, and invest in our future.
• Autonomous and Accountable Teams: We trust our team members to take ownership and make smart decisions. We empower you to be your best self!
• An Escalating Bar for Talent and Performance: We're constantly raising the bar and challenging ourselves to be better. We believe in growth and continuous improvement.
• Fundamental Optimism: We see the glass as half full (and then we fill it up with more amazing ideas!). We believe in the power of positivity and the potential for greatness.

Compensation - At Human Interest, there are a number of factors that are used to determine the appropriate pay range for each position. We take into account the cost of labor for each position in various markets across the U.S. The base salary for this position spans $90,000 - $100,000 annually and represents the minimum in our lowest geographic region to a maximum in our highest geographic region. The salary we offer to a new employee within this range is based on their location within the U.S., their relevant job-related skills, and experience. At Human Interest, base salary is one component of the overall total rewards package. Depending on the position, additional compensation components such as bonuses, commissions, and equity may be offered. All of our employees are offered a robust suite of physical, financial, and mental wellness benefits. In compliance with applicable laws, we do not inquire about salary history, or about criminal history prior to a conditional offer of employment.

Benefits - 

• A great 401(k) plan: Our own! Our 401(k) includes a dollar-for-dollar employer match up to 4% of compensation (immediately vested) and $0 plan fees
• Top-of-the-line health plans, as well as dental and vision insurance
• Competitive time off and parental leave
• Addition Wealth:  Unlimited access to digital tools, financial professionals, and a knowledge center to help you understand your equity and support your financial wellness
• Lyra: Enhanced Mental Health Support for Employees and dependents  
• Carrot: Fertility healthcare and family forming benefits
• Candidly:  Student loan resource to help you and your family plan, borrow, and repay student debt
• Monthly work-from-home stipend; quarterly lifestyle stipend
• Engaging team-building experiences, ranging from virtual social events to team offsites, promoting collaboration and camaraderie.

We’re a great place to work (but don’t take our word for it) 

Here’s a list of our awards and accolades:

• Certified as a Great Place To Work® (2023-2025)
• Fortune Best Place to Work in the Bay Area (2024)
• Best Places to Work by Built In (2023-2024)
• America’s Best Startup Employers by Forbes (2020-2022, 2024) 
• A Top Company by Y Combinator (2020-2023)
• Inc. Fastest Growing Companies (2021)

Human Interest is an equal opportunity employer. All applicants will receive consideration for employment without regard to race, color, religion, sex, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran or military status, pregnancy, or any other characteristics protected under federal, state, or local laws. Employment with Human Interest is at-will, meaning either you or the company may terminate employment at any time, with or without cause or notice, except as otherwise provided by law or written agreement.

We are committed to making every stage of our application process fully accessible to all individuals. If you need a reasonable accommodation at any point in the process, please let us know at applicantaccommodations@humaninterest.com.

Protect yourself against fraud and identity theft. Apply to our open positions directly via our careers page on Greenhouse. Human Interest will never ask applicants for their financial or banking information as part of our application process. All legitimate communication will come from a @humaninterest.com email address. If you have questions, please reach out to us directly at careers@humaninterest.com

Please note Human Interest does not accept unsolicited resumes from any source other than directly from candidates. We will not consider resumes from vendors, including and without limitation search firms, staffing agencies, fee-based referral services, and recruiting agencies. 

Pursuant to the San Francisco Fair Chance Ordinance, we will consider employment-qualified applicants with arrest and conviction records. We comply with CCPA guidelines.

See more: https://humaninterest.com/disclosures