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, LD, 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 i ... (truncated, view full listing at source)