ABOUT OLLY OLLY

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.

WHY WE NEED YOU

At Olly Olly, we’re looking for a hands-on Head of People Operations to build and lead the engine that keeps our team supported, engaged, and thriving. You’ll own all core People Ops functions — from HRIS and payroll to performance management and culture — and lead a small, high-impact team across People Ops and IT Support.
You’ll partner closely with the Talent team, Chief of Staff, and executive leadership to ensure every Olly Olly teammate has a seamless, consistent, and positive experience. You’ll also own change management and communication strategies that help the organization navigate growth, evolve culture, and stay aligned.
This role is crucial to driving a people-first culture that supports company growth and helps Olly Olly teammates do their best work every day.

EXPERIENCE & LEADERSHIP

• 6–10 years of experience in People Ops or HR, including 3+ years in a leadership or owner-level role
• Proven ability to build, own, and evolve People Ops systems and programs from the ground up

SKILLS & EXPERTISE

• Strong HRIS experience (Gusto strongly preferred)
• Hands-on experience managing payroll, benefits, and multi-state HR compliance
• Solid HRBP skills and comfort handling sensitive employee relations with empathy and professionalism
• Strong knowledge of workplace operations and vendor management

Please refer the Job description for details