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.
We understand that it takes a diverse team of highly intelligent, curious, determined, empathetic, and self aware people to grow a successful company. Our HQ is located in New York City, but we have employees located throughout the US, Australia, Canada and South America. We are growing quickly, but deliberately, with a focus on building an inclusive culture. Our dynamic team has incredible perspectives to share, just as we know you do, and we take great pride in being an equal opportunity workplace.
Offices
Roles posted in New York, San Francisco, and Salt Lake City are hybrid positions with on-site expectations of 2-3 days per week in our local offices. For candidates outside of these areas, you may be eligible for our relocation assistance program.
Benefits
For full-time U.S. employees we offer:
- Competitive medical, dental, and vision
- Company equity
- 401(k) plan with company match
- Unlimited paid time off + 13 company paid holidays
- Parental leave
- Flex Cares Program: Non-profit company match + pet adoption coverage
- Free Flex subscription
For full-time non-U.S. employees, we offer:
- Competitive compensation + company equity
- Unlimited PTO
Flex Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Flex and has not been reviewed or approved by Flex.
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Healthcare Strength — Day-1 medical, dental, and vision coverage is explicitly offered and framed as “best-in-class coverage and options,” suggesting strong baseline health benefits. Additional listings also describe broad health-support elements such as IVF/adoption and gender transition benefits, reinforcing depth in healthcare-related coverage.
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Retirement Support — A 401(k) is available, with a stated company match starting in early 2026, indicating improving retirement support. This rollout appears to address earlier gaps where matching was not consistently present.
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Leave & Time Off Breadth — Unlimited PTO plus company holidays (and, in some descriptions, shutdown days) indicates a wide time-off policy on paper. Hybrid work flexibility and office-day meal credits can add to the overall rewards value for NYC-based employees.
Flex Insights
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What We Do
Flex, an NYC-headquartered FinTech company, has created a trusted rent payment experience. It’s hard to believe that it’s 2024 and paying rent on time is expensive, inflexible, and difficult; we’re here to change that! We enable our users to pay rent throughout the month on a schedule that better fits their finances and budget, while also helping them build credit. Our mission is to empower as many renters as possible with flexibility over their most significant recurring expense.
Why Work With Us
We believe it takes a diverse team of curious, determined, empathetic, and self aware people to grow a successful company. We value the unique and dynamic perspectives our team brings to solve critical problems that impact the lives of our users and the financial decisions they make.
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