Director of People Operations

Director of People Operations 

Join Us!

HealthCare.com has become one of America’s fastest-growing insurtech companies, revolutionizing how consumers shop for health insurance. Leveraging advanced technology and data science, the company has developed customized proprietary products to better fit consumer requirements, enhance customer satisfaction, and take some of the guesswork and inefficiencies out of buying insurance.

 

The Opportunity 

We are looking for a strategic builder and a holistic People Operations leader to serve as our Director of People Operations. As a company of ~130 employees and targeting for growth, we require an executive to architect scalable systems for talent, culture, and compliance across the organization. Reporting directly to the CEO, you will be the driving force behind our strategic people roadmap, focusing on manager development, organizational design, total rewards, and operational excellence. You will also oversee the day-to-day HR engine, ensuring our operations are compliant, efficient, and scalable. 

You will lead a capable team of two, giving you the leverage to focus on strategy, organizational design, and coaching while ensuring the operational engine runs flawlessly. 

 

Core Responsibilities 

Manager Training Programs (The "Resource" Function) 

• Training Curriculum: Design and deliver "Manager 101" and advanced training programs on the fundamentals of leadership: effective interviewing, running 1:1s, delivering critical feedback, and managing compensation discussions. 
• The "Hard" Skills: Train managers on how to document performance issues, conduct Performance Improvement Plans (PIPs), and handle terminations legally and empathetically. You will teach them how to fish, not just fish for them. 
• Executive Coaching: Serve as the trusted confidante and advisor to the executive team and department heads on organizational dynamics and complex people challenges. 

Assessments, Strategy & Org Design 

• Total Rewards Architecture: Design a compensation philosophy that attracts and retains top talent. Build salary bands, variable commission plans, and equity structures that align with business goals while protecting the bottom line. 
• Psychometrics & Assessments: Implement and utilize psychological and behavioral assessments (e.g., Predictive Index, DISC, StrengthsFinder) to improve hiring accuracy, enhance team communication, and optimize organizational design. 
• Retention Strategy: Use data (eNPS, retention rates) to identify flight risks and proactively address cultural or structural issues before they impact the business. 

Culture, Morale & Career Development 

• Career Pathways: Build clear, actionable career development pathways for key roles. Ensure high performers can visualize their future at the company, increasing retention and engagement. 
• Company Rhythm: Own the design and execution of company All Hands meetings and culture events. You are responsible for the "pulse" of the organization—ensuring morale is high and communication is clear. 
• Performance Culture: Elevate our performance management process from a compliance task into a key strategic system for continuous team upgrade, rigorously identifying and developing high-potential 'stars' and addressing underperformance to ensure high talent density across all levels. 

Operations, Compliance & Infrastructure 

• Onboarding/Offboarding: Oversee the People Ops Administrator to ensure onboarding and offboarding are efficient and compliant. 
• Risk Management: Serve as the final escalation point for investigations and compliance matters (EEO, FLSA, FMLA). Ensure managers understand the legal boundaries of their roles. 
• Talent Acquisition Oversight: Oversee the Corporate Recruiter to ensure we are executing a highly selective and efficient hiring strategy focused on raising talent density. 

 

Qualifications 

• Experience: 8-10+ years of HR experience, ideally in a high-growth environment (e.g., scaling from 50 to 150+ employees). 
• Comp Design: You have built compensation and equity plans including STI and LTI (Excel proficiency is a must). You are familiar with establishing pay structures, plan design, rewards design and implementation. 
• Assessment Expertise: Experience using psychometric or behavioral assessment tools to guide hiring and team-building decisions. 
• The "Coach" Mindset: Proven track record of training and enabling managers. You are comfortable role-playing a difficult conversation with a VP. 
• Certifications: SHRM-SCP or SPHR strongly preferred. 

 

Why Join Us? 

You will be the architect of our entire People and Performance Culture strategy. This isn't just about compliance; it's about leading a growing company through its next phase by building scalable systems for talent development, equitable rewards, high-performing management, and a thriving culture. If you are passionate about these items and having an impact on business performance in a high-growth setting, this is the role for you.