Director, HR Technology & Automation

Flex is a growth-stage, NYC headquartered FinTech company that is creating the best rent payment experience. It’s hard to believe that it’s 2026 and paying rent on time is expensive, inflexible, and difficult. We’re here to change that! Flex enables our users to pay rent throughout the month on a schedule that better fits their finances and budget. Our mission is to empower as many renters as possible with flexibility over their most significant recurring expense. After deliberately keeping a stealth profile as we built up unprecedented investor support and an enthusiastic user base, we are looking for motivated individuals to help us keep our mission growing. Will you be a part of the team? About the Role Flex is seeking a strategic and forward thinking Director, HR Technology Automation to own and accelerate our HR technology ecosystem, drive automation across HR processes, and build out our AI-driven HR strategy. This leader will shape the future of HR operations by partnering with People Operations, IT, and business stakeholders to optimize systems, enhance data and reporting capabilities, and embed intelligent automation and AI tools that improve employee experience and organizational efficiency. This is a hybrid position with on-site expectations of 3 days per week in our New York Headquarters (a few blocks from Union Square) or 2 days per week in our SF Hub. For candidates outside of the NY/NJ or SF area, you may be eligible for our relocation assistance program. What You'll Do HR Systems Leadership Strategy Lead the overall strategy, governance, roadmap, and operations for HR systems (HRIS, ATS, LMS, performance, workforce planning, and related platforms) Serve as the subject matter expert and key liaison between HR, IT, vendor partners, and business stakeholders Ensure HR systems are scalable, secure, compliant, and aligned with business priorities Automation AI Strategy Define and lead Flex’s HR automation and AI strategy, identifying opportunities to streamline workflows, improve data quality, and enhance employee and manager experiences Evaluate, pilot, and scale AI-enabled tools across HR processes Partner closely with IT and external vendors to integrate automation and AI capabilities into the broader technology ecosystem Data Reporting Evolve HR metrics, dashboards, and analytics to drive decision making for the People team and leadership Ensure high data integrity, documentation, and governance across HR platforms Change Management Adoption Drive change management, training, and enablement to ensure strong adoption and effective use of HR systems and tools Translate business and People needs into clear system requirements and scalable solutions Key Qualifications 8+ years of experience in HR systems, HR technology, HRIS management, or related functions Strong technical understanding of HRIS platforms and integrations Demonstrated experience leading cross functional technology initiatives Familiarity with AI tools, automation platforms, and their application in HR processes Excellent analytical and data visualization skills Experience scaling HR systems in a hyper growth company Flex takes a market-based approach to pay, ensuring compensation is commensurate with a candidate's experience and our internal leveling guidelines. For candidates located in our Tier 1 markets (NYC/SF/Seattle), the base salary pay range for this role is $204,000 - $255,000 USD. For all other U.S. locations, Flex utilizes a geographic pay differential based on a cost of labor index. If you are located outside of the Tier 1 states listed above, your starting pay will be adjusted to align with the market conditions of your specific geographic zone. Please speak with your recruiter for additional information regarding the specific range for your location. Life at Flex: We understand that it takes a diverse team of highly intelligent, curious, determined, empathetic, and self aware people to grow a successful c ... (truncated, view full listing at source)