People Operations Leader

EnrollHere, Inc.; United States; Remote; USD 75,000 - 135,000; Full time

Job summary

EnrollHere, Inc., a rapidly scaling SaaS company, is searching for a People Operations Leader to manage the full lifecycle of employee engagement and compliance. This executive role involves strategic partnership with the CFO and is crucial for shaping a high-performance culture. Candidates should bring extensive HR experience in high-growth settings and a passion for inclusive, agile workplace practices.

Benefits

Comprehensive health, dental, and vision insurance

401(k) with company match

Performance-based bonus potential

Equity grants aligned with company milestones

Remote-first work flexibility

Qualifications

• 7-10 years in people-operations/HR roles in InsurTech, FinTech, or SaaS.
• Experience with PEOs like Justworks for payroll and compliance.
• Deep knowledge of U.S. employment law across multiple states.

Responsibilities

• Architect and manage the full employee lifecycle from recruiting to performance management.
• Design onboarding processes and ensure compliance with HR policies.
• Run quarterly engagement surveys and facilitate recognition programs.

Skills

Project Management

Communication

Stakeholder Influence

Recruiting

Performance Management

Employee Engagement

Job description

4 days ago Be among the first 25 applicants

Enroll Here is a profitable, fast-scaling SaaS company that modernizes how insurance is bought, sold, and serviced. By streamlining quoting, enrollment, and policy management, we give brokers and carriers a competitive edge in today’s digital marketplace. As we continue our rapid expansion, we’re investing in a world-class people function that attracts and retains top talent.

Role Summary

As our first dedicated People Operations Leader, you will architect and manage the full employee lifecycle—from recruiting and onboarding through performance management and engagement—while ensuring multi-state compliance. You will report directly to the Chief Financial Officer and partner with the executive team to build scalable, culture-forward people programs for our distributed workforce.

Focus Areas

Talent Acquisition

• End-to-end hiring for technical and business roles (software engineers, product, GTM, support, compliance coordinators).

• Build role scorecards, sourcing strategies, and an interview process that balances speed and quality.

• Maintain an applicant-tracking/PEO pipeline and deliver clear recruiting metrics.

Onboarding & Offboarding

• Design and facilitate a consistent 30-60-90-day onboarding journey (pre-boarding checklists, IT provisioning, cultural immersion).

• Coordinate offboarding to ensure knowledge transfer, asset return, and compliant separations.

Performance & Development

• Launch and administer annual and mid-year performance-review cycles (goal-setting, calibration, feedback loops).

• Support managers with training on coaching, feedback, and career-growth conversations.

Employee Engagement & Culture

• Run quarterly engagement surveys, analyze results, and partner with leadership on action plans.

• Facilitate recognition programs and virtual events that connect a remote team.

HR Policy & Compliance

• Draft, update, and communicate policies in line with FLSA, ADA, Title VII/EEO, state wage-hour, pay-transparency, ACA, COBRA, and harassment-prevention rules.

• Serve as point of contact to our PEO (Justworks) for payroll, benefits, and compliance audits.

What You Bring

• 7–10 years people-operations/HR experience in InsurTech, FinTech, or high-growth SaaS.
• Proven success running recruiting, onboarding, performance, and engagement programs end-to-end.
• Deep working knowledge of U.S. employment law across multiple states.
• Hands-on experience with a PEO (Justworks, Rippling, TriNet, etc.) for payroll, benefits, and compliance.
• Strong project-management, communication, and stakeholder-influence skills—the ability to drive programs with minimal direction.
• Passion for building inclusive, high-performance cultures and scaling processes in a remote-first environment.
• Base Salary: $75,000 – $135,000 (commensurate with experience, skill set, and geographic cost of labor).
• Bonus & Equity: Performance-based bonus potential plus equity grants aligned with company milestones.
• Comprehensive health, dental, and vision insurance via Justworks.
• 401(k) with company match

Why Enroll Here

• Mission-Driven: We’re transforming an industry that impacts millions of consumers.
• Growth Stage: Join early enough to shape the culture, yet late enough to leverage product-market fit and healthy revenue.
• Influence & Ownership: Report directly to the CFO and build the entire people function from scratch.
• Remote-First Flexibility: Work where you’re most productive while staying connected through intentional virtual collaboration.

Seniority level

• Seniority level

  Executive

Employment type

• Employment type

  Full-time

Job function

• Job function

  Human Resources

• Industries

  Software Development

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