HR Technology & Operations Lead

Why us?

Insurify is one of America’s fastest-growing MIT FinTech startups and has been recognized as one of Inc. 5,000’s fastest-growing private companies in America in 2025, 2024, 2023, 2022 and 2021, Forbes Fintech 50 List for 2023, 2022, and 2021, Forbes Next Billion Dollar Startups of 2022 global and Top 100 InsurTech company. We’re changing the way millions of people compare, buy and manage insurance with artificial intelligence, technology, and superior product design.

How you will make an impact

• Own and evolve our HR systems (e.g., Rippling, Greenhouse), including configuration, integrations, and ongoing improvements to how they support the business
• Connect and integrate data across systems, ensuring information flows seamlessly and is consolidated into a single, reliable source of truth
• Build and scale HR operations across the employee lifecycle, creating simple, effective processes that are easy to use and built to grow with us
• Ensure our data is accurate, connected, and useful—building dashboards, reporting, and insights that help leaders understand trends and make better decisions
• Lead the migration and integration of historical and current data across systems, helping create a single, reliable source of truth
• Identify gaps or inefficiencies in how we operate, and design practical solutions that improve both accuracy and employee experience
• Own and strengthen our approach to HR compliance, ensuring our processes and systems meet legal requirements and are audit-ready
• Oversee payroll and benefits through a dedicated team member, supporting their growth and development while ensuring these programs run smoothly and effectively
• Partner closely with People, Finance, IT, and business leaders to connect systems, improve workflows, and support company growth
• Balance long-term thinking with day-to-day execution, stepping in wherever needed to move work forward
• Provide structure, prioritization, and support across the broader HR operations space, even when work is distributed

Who you are

• 5-7+ years of experience in HR operations, HR systems (HRIS), or people operations roles, ideally in a scaling or fast-moving environment
• Strong experience with HR technology (e.g., Rippling, Greenhouse), including implementation, integrations, and building the operational infrastructure that supports them
• Comfortable owning both strategy and execution—you like building things and getting into the details
• Experience creating or improving HR processes and systems that scale, with ownership from design through execution
• Strong understanding of HR data, with the ability to turn it into clear, useful insights
• Familiarity with HR compliance and US employment law as it relates to HR operations
• Experience working with or overseeing payroll and benefits
• Experience with compensation programs and related data (e.g., benchmarking, salary reviews) is a plus
• High attention to detail, with a strong sense of ownership over accuracy, quality, and data integrity across tools and processes
• Practical and solutions-oriented, with the ability to simplify complex problems

Benefits

• Competitive compensation
• Generous stock options
• Health, Dental Coverages
• 401K plan with match
• Unlimited PTO
• Generous company holiday calendar
• Learning & Development Stipends
• Paid Family Leave
• Social impact volunteer time
• Catered lunches in the office