HR Technology & Operations Lead

Warning: Fraudulent Job Adverts Beware of fraudulent activities claiming to represent Insurify. We are not associated with any entities soliciting personal information or payment. The safety of our job seekers is a top priority, and we actively work to prevent such incidents. Insurify will never request sensitive information or payment during the hiring process. Be cautious of text-only interviews, interviews conducted through Microsoft Teams, or suspicious offer letters. 
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.

Our company vision is to be recognized as the preeminent and most trusted digital agent for insurance comparison, purchase, and management. Our team is critical to achieving our vision and fostering the right culture is essential to our team’s success.

Join us if you like

• $1.3 Trillion market opportunity
• MIT alumni founders
• Female-led startup
• $130M total funding
• Strong leadership team with experience from many successful startups around the world

How you will make an impact

We’re looking for a HR Technology & Operations Lead to build and scale the backbone of our People & Culture function. This role owns the systems, processes, and data that power the employee lifecycle, ensuring our HR infrastructure is accurate, efficient, and built to scale. This role is foundational to how our People function operates and scales.

We’re looking for someone who brings structure to complexity, is systems-minded and comfortable with data, and understanding how processes work in practice for people.

You’ll lead our HR technology strategy (including Rippling, Greenhouse,etc.), build and evolve HR operations, compliance, and analytics, and oversee payroll and benefits through a team member. This is a hands-on role with broad scope and visibility, blending strategy and execution to build scalable systems, strong processes, and enable us to better use our people data to inform decisions.

In this role, you will:

• 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

Insurify is committed to offering a fair, competitive, and transparent compensation program that supports our mission to attract, retain, and motivate top talent. Our compensation philosophy is guided by several factors including a candidate’s relevant experience, education/training, job-related skills, and location.

In addition to the base salary our total compensation package includes health coverage, retirement contributions, and additional wellbeing benefits. Some positions may be eligible for company equity.

Below is the base compensation range for US locations:

$140,000-$160,000