Head of People

Why us? 

Insurify is one of the 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 start-up’s around the world

Insurify is seeking a strategic, people-first Head of People to lead our human resources function through its next phase of growth. This role is critical in shaping the systems, values, and people practices that power a diverse, high-performing, and supportive culture. You’ll partner closely with the executive team to align people strategy with business objectives while building and evolving the programs that attract, retain, and grow world-class talent.

We’re looking for a collaborative, thoughtful leader who brings strong experience across HR strategy, organizational design, performance management, and culture-building, and who thrives in a fast-paced, high-change environment.

How you will make an impact

Strategic Leadership

• Evolve and drive Insurify’s people strategy aligned with company vision and growth objectives.
• Serve as a trusted advisor and thought partner to the CEOs and leadership team on workforce planning, org design, leadership development, and change management.
• Track and report on people-focused OKRs using data to guide decisions and demonstrate impact.

Culture, Inclusion & Engagement

• Foster a warm, inclusive, and values-driven culture across our hybrid and international teams.
• Lead efforts to strengthen DE&I through policies, programs, education, and representation at all levels.
• Develop and own the company’s approach to employee engagement, belonging, and recognition.

Talent & Organizational Development

• Design and implement performance development programs with clear feedback and growth pathways.
• Build scalable manager enablement resources, including training, coaching, and leadership development tools.
• Champion a culture of learning by launching accessible L&D initiatives.

Compensation, Benefits & Total Rewards

• Refine and execute a compelling total rewards strategy that attracts, motivates, and retains top talent.
• Partner cross-functionally to align compensation with performance and market data.
• Oversee benefits, wellness, and leave programs, with a focus on inclusivity and employee experience.

People Operations & Compliance

• Lead the People Ops function, including HR systems, policies, benefits, immigration, and compliance.
• Ensure compliance with all applicable federal, state, and international employment laws and standards.
• Provide oversight of global operations, including our Bulgaria-based team, and manage immigration and visa processes.

Hiring & Workforce Planning

• Strengthen talent acquisition strategy and recruiting operations.
• Expand sourcing channels and partnerships to increase diversity in our hiring pipelines.
• Support team leads in forecasting, headcount planning, and org structure evolution.

Who you are

• Highly motivated to start, follow through, and complete projects 
• Strategic thinker that is also willing to roll up your sleeves to get things done 
• Leads well under pressure with calm and sound judgment
• Great listener able to offer actionable advice; excellent communicator
• Team builder and coach who cultivates a growth mindset within the organization
• High social and emotional intelligence, highly ethical individual with unquestioned integrity
• Proven ability to address sensitive people and business issues with discretion and confidentiality
• Thorough knowledge of employment-related laws and regulations
• Experience working internationally across many different cultures 
• Ability to come into the Cambridge office 

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
• Commuter Benefits