Senior People Operations Manager

Overview Ready to roll up your sleeves and help transform local marketing forever? At Olly Olly, we’re blending technology and real-world expertise to empower businesses across the U.S. like never before. We believe small businesses are the backbone of our economy. That’s why we’re on a mission to provide them with tools, strategies, and insights that help them rank higher, generate high-quality leads, get calls and reviews, and, above all, grow sustainably, without the hassle. The Olly Olly platform complements our hands-on service perfectly: it’s no-nonsense, easy-to-use software that helps local businesses streamline operations and contact management, drive leads, stabilize cash flow and maximize revenue with minimal effort, so they can reclaim their time to focus on what they do best. We aim to be the ultimate all-in-one platform for small-business growth — where automation, AI, and human expertise work together to deliver consistent, measurable results. We started as an agency and have helped thousands of clients succeed. Today, we’re in a pivotal transition to a SaaS-first company, building scalable systems that support high-volume execution without sacrificing quality. 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 theHR 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. Why This Role Exists 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 The Impact You’ll Have HR Operations & Compliance (Core Ownership) 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 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 HR Business Partner – Sales & Customer Success 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 Oversee and manage day-to-day work of the PeopleOps team, including: 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 What We Really Need From You 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 What Would Be Big Pluses Hands-on experience with Gusto HRIS Experience stabilizing or migrating HR systems Exposure to multi-state or distributed and global workforces What Success Looks Like (First 3-6 months) Payroll, benefits, and HRIS are stable, audited, and running without escalations Employee data is accurate, compliant, and reliable across systems Clear, documented employee lifecycle processes are in place and actively used Sales & CS leaders trust PeopleOps as a practical, risk-aware partner Open compliance or people-risk issues are identified, documented, and addressed What You’ll Love About Working at Olly Olly Salary based on experience Schedule: Monday–Friday, 8:00 AM – 5:00 PM 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. Join us during this pivotal transition as we transform from an agency to a human-centric SaaS provider. Your ideas, strategies, and solutions will directly impact the success of small businesses. And our own growth! Let’s shape the future of small business growth together! Apply now to join a team that’s as committed as they are supportive of each other. Diversity and Inclusion at Olly Olly At Olly Olly, we celebrate differences in background, culture, abilities, and perspectives because diversity drives innovation and creativity. Your voice matters here, it really does! And your unique perspective will help us shape the future of smallbusiness growth. #J-18808-Ljbffr Olly Olly