AI Enablement and Transformation Lead (HR)

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

We are looking for an AI Enablement and Transformation Lead to join our People team with a focused mission: transforming how our organization works by embedding AI into the way our People team operates and delivers programs company-wide. 

This role is purpose-built for someone who understands both the craft of HR and the power of AI — and who gets excited about unlocking new levels of impact through smarter, faster, and more human-centered ways of working. You'll partner across all People functions — from Talent Acquisition and Total Rewards to our People Business Partners and People Operations teams — identifying opportunities to integrate AI tools, upskilling AI proficiency, and building the internal capability that makes transformation stick.

This isn't a training-room-only role. You'll be a strategic partner, a hands-on coach, and a change agent embedded within the People team.

What you get to do every day

HR AI Strategy & Roadmap

• Develop and own an AI enablement strategy specifically for the HR organization, aligned to the broader People team priorities and business goals
• Partner with HR leadership to identify the highest-value opportunities for AI integration across HR workflows, processes, and programs
• Build a prioritized roadmap for AI adoption across HR functions, balancing quick wins with longer-term capability building

Internal Upskilling & Training

• Design and deliver tailored AI learning experiences for employees at all levels across the company — from foundational literacy to advanced, function-specific application
• Create role-based learning paths for key HR personas (e.g., PBPs, Recruiters, L&D, People Operations) that connect AI skills directly to their daily work
• Facilitate hands-on workshops, peer learning sessions, and coaching that build real confidence and fluency with AI tools

HR Process & Workflow Innovation

• Conduct discovery sessions with HR sub-teams to map current workflows and identify where AI can reduce friction, improve quality, or free up capacity
• Lead end-to-end implementation of AI-powered solutions across HR workflows — from scoping and design through piloting, launch, and iteration
• Pilot and scale AI-assisted approaches across common tasks — such as job description writing, candidate screening support, employee communication drafting, data analysis, and more
• Document new AI-enabled workflows and develop enablement resources (playbooks, templates, job aids) that make adoption easy and sustainable

Governance & Responsible Use

• Champion responsible and ethical AI use, ensuring all AI-assisted workflows comply with data privacy standards, employment law, and company policy
• Partner with Legal, Compliance, and IT to establish guardrails and best practices for AI use

Measurement & Continuous Improvement

• Define success for AI adoption
• Gather ongoing feedback from team members and use insights to iterate on programs, resources, and coaching approaches
• Report regularly to leadership on adoption trends, impact, and emerging opportunities

What you bring to the role

• 2+ years of experience in core HR functions, Learning & Development, or HR Operations preferred
• 3+ years of direct experience with AI tools in a professional context, with a strong understanding of how AI applies to workflows specifically
• Ability to craft effective prompts for a variety of HR workflows (job descriptions, communications, data analysis, etc.)
• Understanding of how LLMs work at a conceptual level — enough to teach others and troubleshoot outputs
• Knowledge of AI limitations, hallucinations, and how to quality-check AI-generated content
• Proven ability to influence and drive adoption— making AI approachable, relevant, and immediately useful
• Experience designing and facilitating training or enablement programs in a corporate setting
• Strong consultative skills — able to partner with stakeholders, diagnose needs, and build practical solutions
• Familiarity with HR platforms such as Workday, Greenhouse, Docebo or similar preferred
• Deep Experience with AI tools such as Gemini and Claude
• Knowledge of responsible AI principles and data privacy considerations
• Proven success in change management or organizational effectiveness

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 $120,000 - $135,000 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