HR Operations Manager

Clasp is a venture-backed, mission-driven startup transforming access to education and career pathways. We are revolutionizing the way employers attract and retain critical talent, while simultaneously tackling the student debt crisis. (Yep, we think BIG.) Our innovative platform meaningfully connects employers, educational institutions, and diverse talent to drive mutual benefit—using accessible education financing as the thread. We like to think of ourselves as more than a fintech; we’re a catalyst for economic mobility.

A Forbes Fintech 50 company, portfolio company of SHRM (Society of Human Resource Management, the largest HR organization out there!) and recipient of “18 most promising startups in healthcare” by Business Insider, Clasp is driven by our commitment to social impact and innovation. We are reshaping the future of the workforce one opportunity at a time. Join us on our journey to give power to learners and unlock fulfilling careers that drive positive change in their communities and beyond.

What You’ll Do

Benefits Ownership

• Own Clasp’s employee benefits program end to end- from analyzing current offerings and gathering employee feedback, to benchmarking against external market standards, to recommending and implementing changes
• Lead annual benefits renewals from start to finish, including plan evaluation, negotiation, and rollout
• Own and execute company-wide open enrollment, including employee education, communication, and enrollment support
• Serve as the primary point of contact and day-to-day relationship owner for all external benefits vendors, brokers, and carriers
• Monitor plan utilization, cost trends, and employee satisfaction to keep our offerings competitive and cost-effective as we scale
• Ensure all benefits programs remain compliant with applicable regulations (ACA, COBRA, ERISA, and related requirements)

HR Operations & Process Management

• Manage our day-to-day PEO relationship (currently Justworks), including HRIS administration and data integrity
• Lead a comprehensive audit of our current PEO/HRIS setup and own the project to evaluate whether Clasp should remain on a PEO model or transition to an alternative HR infrastructure by 2027, including recommending and executing next steps
• Own the administrative execution of onboarding (I-9 verification, background checks, new hire documentation, system provisioning) and offboarding (documentation collection, equipment return, system deactivation)
• Manage 401(k) match and equity data updates in Carta, ensuring accuracy between HRIS, payroll, and cap table systems
• Conduct a comprehensive audit of existing HR processes to identify gaps, and design and implement updated, scalable processes and documentation
• Identify and drive opportunities to streamline and automate HR administrative workflows

Compliance & Risk Management

• Manage all leave of absence requests and processes, including FMLA and state paid family/medical leave programs (PFMLA)
• Serve as the primary point of contact for unemployment claims and tax-related audits or inquiries
• Own Clasp’s employee handbook, partnering with Compliance and Security teams on regular review, updates, and audit response
• Maintain (or know how to quickly obtain) working knowledge of state-by-state HR compliance requirements, and proactively monitor and communicate regulatory changes to the business
• Own employment verification and reference check requests (e.g., background check vendors, mortgage/loan verifications)
• Serve as the primary point of contact for HR-related compliance audits and regulatory inquiries

What You’ll Need

• 5+ years of progressive HR experience, with significant ownership of benefits administration and PEO/HRIS management
• Hands-on experience managing a PEO relationship (Justworks experience a strong plus) and evaluating HR infrastructure options
• Strong experience in benefits administration — plan design and evaluation, renewals, open enrollment, and vendor/broker management
• Working knowledge of federal and state leave laws (FMLA, PFMLA) and multi-state employment compliance
• Experience managing the administrative side of onboarding and offboarding, including I-9 and background check compliance
• Strong process orientation, with experience auditing and rebuilding HR workflows and documentation
• Comfort operating as the primary owner of HR operations in a lean, fast-paced environment
• Excellent communication and vendor/stakeholder management skills
• SHRM-CP, PHR, or similar HR certification a plus

What We Give In Return

• Competitive cash and equity compensation
• Medical benefits (health, dental, & vision)
• 401k matching
• Flexible PTO policy
• Opportunities to grow and perform in a fast-paced environment alongside a stellar team.