Job Description

Given that this position requires English proficiency, we are only considering CVs provided in English. Thank you, and we look forward to your submission!*
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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.

Our Vision

We aim to be the ultimate all-in-one platform for small business growth, allowing owners to manage every part of their business efficiently and effortlessly.


Our journey began as an agency, and we've already helped thousands of clients succeed. Now, we're embracing an exciting new chapter: becoming a SaaS-first company. By combining hard-earned human expertise with AI and automation, we're creating affordable solutions that give business owners peace of mind while driving measurable success.

Why We Need You

We are seeking a

PeopleOps Generalist

to join our offshore People Operations team and provide broad HR support across payroll, benefits, onboarding, offboarding, employee records, and day-to-day HR administration. This role ensures the smooth running of core People Ops processes while our US-based team focuses on compliance, employee relations, and strategic initiatives.


The ideal candidate is detail-oriented, proactive, and thrives in a fast-paced environment. You'll wear many hats — supporting payroll cycles, onboarding/offboarding new hires, maintaining employee data, and serving as a go-to resource for HR operations. In addition, you'll partner with managers across business functions to help navigate HR-related questions and cases aligned with company policies (e.g., attendance, performance documentation, leaves, and policy clarifications).

The Impact You'll Have

Payroll & Benefits

Process semi-monthly payroll in Gusto (or similar HRIS/payroll software). Ensure accuracy of employee pay, contractor invoices, bonuses, and deductions. Administer benefits enrollment, changes, and terminations (US health benefits, PTO, offshore benefits tracking). Serve as first point of contact for employee payroll and benefits questions.

Employee Lifecycle Support

Support onboarding and offboarding logistics: + Set up new hires in HRIS, prepare documentation, coordinate with IT for equipment.
+ Process final payroll, benefits termination, and exit records.
Maintain accurate employee records and HRIS data (personal info, role changes, location updates). Respond to standard employment verification and reference checks.

HR Operations & Administration

Support PTO, leave, and attendance tracking across US and offshore teams. Ensure all employee data and documentation are compliant and up to date. Assist with HR communications, templates, and process documentation. Maintain confidentiality and handle sensitive employee information with discretion.

HR Support Across Business Functions

Serve as a resource for managers and team leads across departments on navigating People Ops processes and policy-aligned decisions (e.g., attendance issues, policy interpretation, documentation best practices). Guide leaders on proper steps and documentation for performance conversations, while escalating more complex or sensitive matters to the People Executive. Support the implementation and consistent application of company policies and practices across the organization.

People Ops Support

Partner with our People Executive on projects (e.g., engagement surveys, policy updates, audits). Support People Ops processes and checklists to ensure consistency and accuracy. Escalate complex employee relations or compliance matters to the People Executive.

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What We Really Need From You

3+ years of experience in HR operations, payroll, or generalist roles (US payroll experience strongly preferred). Familiarity with HRIS and payroll systems (Gusto, ADP, Paylocity, or similar). Experience administering benefits (US or international preferred). Strong organizational skills with high attention to detail. Excellent English communication skills (written and verbal). Proven ability to prioritize and meet deadlines in a fast-paced environment. Discreet and professional when handling sensitive employee information.

What You'll Love About Working at Olly Olly

Competitive pay based on your experience. Flexible work: 100% remote; Monday-Friday, 8:00 am - 5:00 pm CST. Work-life balance: Generous PTO, including 15 vacation days and U.S. holidays.

Why Choose Us?

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 & 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 small business growth.