Senior People Operations Manager

Olly Olly • Austin, TX

2d • Onsite

About The Position

The Senior People Operations Manager is a senior, hands-on PeopleOps leader responsible for stabilizing HR operations, ensuring compliance, and reducing people-related risk while serving as the HR Business Partner for Sales and Customer Success.
This role is designed for a startup-tested operator who can clean up fragmented systems, build practical and scalable People processes with a limited tech stack, manage contractors, and partner confidently with executives and frontline managers.
This is not a policy-only or advisory role. This is a doer + stabilizer role in a fast-paced, in-office startup environment.
Olly Olly is in a critical phase of growth where People Operations fundamentals must be stabilized to support performance, compliance, and scale — particularly across Sales and Customer Success.
This role puts a U.S.-based senior PeopleOps operator in place to:
Close operational and compliance gaps
Own payroll, benefits, and HR systems end-to-end
Standardize the employee lifecycle
Act as a trusted, risk-aware HR partner to Sales and CS leadership

Requirements

• 6–10 years of progressive People Operations / HR experience
• Prior experience in a startup or high-growth environment
• Demonstrated ownership of payroll, benefits, and HR compliance
• Experience supporting Sales and/or Customer Success teams as an HRBP
• Experience managing contractors and vendors
• Working knowledge of global contractor populations
• Strong judgment, discretion, and ability to handle sensitive employee matters
• Ability to build practical processes without relying on heavy systems or tooling
• Comfort working fully in-office in a fast-paced environment

Nice To Haves

• Hands-on experience with Gusto HRIS
• Experience stabilizing or migrating HR systems
• Exposure to multi-state or distributed and global workforces

Responsibilities

• Own People Operations and HR compliance end-to-end
• Own payroll, benefits administration, and employment-related tax compliance, ensuring accuracy, timeliness, and adherence to applicable regulations
• Serve as primary owner of payroll processing, audits, reconciliations, and issue resolution
• Lead HRIS stabilization and cleanup (Gusto knowledge preferred; migration experience a plus)
• Ensure accurate employee data, tax documentation, and reporting across systems
• Own the full employee lifecycle: pre-onboarding → onboarding → performance management → retention → offboarding
• Lead company orientation and new-hire onboarding sessions
• Audit, maintain, and update HR policies, handbooks, and People documentation
• Build scalable, compliant PeopleOps processes using a limited tech stack
• Demonstrate working knowledge of global contractor populations and associated operational and compliance considerations
• Serve as the primary HR Business Partner for Sales and Customer Success teams
• Partner with leaders on: Performance management, coaching, and corrective action processes Role clarity, expectations, and org structure input Employee relations guidance and issue escalation
• Support sensitive employee situations with sound, risk-aware judgment
• Provide practical, non-legal HR guidance grounded in compliance and business realities
• PeopleOps Generalist – Payroll & Benefits
• PeopleOps Generalist – HR Operations, Facilities, and Events
• Partner closely with Recruiting on: High-volume hiring support Onboarding readiness and coordination Manager enablement and hiring process consistency

Benefits

• Comprehensive benefits (medical, dental, vision, etc.)
• Work-life balance: Generous PTO, including 15 vacation days and U.S. holidays.
• Growth-oriented culture: Join an inclusive, international, and innovative team where your contributions make a tangible difference.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed