Head of People Operations bei Olly Olly

👋 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

At Olly Olly, we’re looking for a hands-on builder and strategic leader to join our leadership team and serve as our Head of People Operations — someone excited to design, scale, and continuously improve the engine that keeps our team supported, engaged, and thriving.

You’ll own all core People Ops functions, from HRIS and payroll to HR business partnership, global workforce strategy, employee relations, performance, and culture, and lead a small, high-impact team across People Ops, IT Support, and a US office location ambassadors. 

You’ll partner closely with the Talent team, Chief of Staff, and executive leadership to ensure every Olly Olly teammate — whether employee or contractor, domestic or international — has a seamless, consistent, and positive experience. You’ll also build and iterate new programs, policies, and systems from the ground up to help the organization scale, evolve, and stay aligned through rapid growth.

🚀 The Impact You’ll Have

Team Leadership & People Operations

• Leading and developing our People Ops team and IT Support Specialist to deliver top-notch service across the business
• Owning, building and evolving People Ops systems and processes (including Gusto HRIS), driving accuracy, automation, and scalability
• Owning payroll, benefits, compliance, and leave administration — partnering closely with Finance and external vendors
• Acting as a trusted HR Business Partner (HRBP) — coaching managers, proactively advising on org design, and handling sensitive employee relations issues with care and discretion
• Supporting conflict resolution, investigations, and performance conversations in partnership with leadership
• Owning onboarding and offboarding in partnership with Talent to ensure a smooth and consistent employee journey
• Building strong partnerships with other departments (Sales, CS, Product, etc.) to align people strategies with broader business goals

Workplace & IT Operations

• Overseeing workplace operations and keeping our offices running smoothly, including facilities and vendor management
• Managing IT support operations, ensuring tools, equipment, and systems work reliably across our hybrid and remote teams

Compensation, Performance & Benefits

• Driving open enrollment, vendor relationships, and benefits education for all employees
• Building out and leading performance review cycles, including rollout, training, and continuous improvement
• Building out and managing compensation and leveling frameworks — role definitions, career paths, and calibration
• Conducting regular market analysis to keep compensation and benefits competitive and aligned with company goals

Culture, Communication & Change Management

• Owning all cultural and engagement initiatives, including internal communications, company rituals, recognition programs, and team-wide events
• Partnering with the Chief of Staff and Talent team to align on company culture, communication strategies, and the overall employee experience
• Leading change management initiatives that support organizational growth and help teams adapt smoothly

Data & Continuous Improvement

• Building and using people data and insights to inform decisions, build reports, and drive continuous improvement
• Owning our company engagement survey efforts and translating insights into action

✈️Travel: 1 office visit minimum per quarter 

✅ What We Really Need From You

 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 preferred)
• Hands-on experience managing payroll, benefits, and multi-state HR compliance
• Deep experience supporting both full-time employees and global contractor workforces, including knowledge of local employment laws, EOR partnerships, and engagement best practices
• Demonstrated HRBP expertise: proven track record supporting leaders with coaching, employee relations, organizational development, and conflict resolution
• Strong knowledge of workplace operations and vendor management

Work Style & Culture Fit

• Excitement for hybrid work and willingness to be in the Austin office regularly — part of a culture that values flexibility and connection
• GRIT — you thrive on challenges and persist with a take-action attitude
• Exceptional communication and collaboration skills — you’re comfortable influencing and partnering across teams
• Experience thriving in a fast-paced, dynamic environment with evolving priorities and ambiguity

➕ What Would Be Big Pluses

• Experience supporting high-volume sales organizations
• Experience managing or partnering with offshore or globally distributed teams
• Exposure to total rewards strategy or compensation design
• Familiarity with change management and scaling internal systems
• Background in tech, SaaS, or digital marketing startups

🌟 What You’ll Love About Working at Olly Olly

• High-impact role where your work directly contributes to company and client success.
• Remote-friendly, fast-paced, and collaborative team environment.
• Growth-focused culture with real opportunities for career development.
• A chance to build and innovate inside a scaling, SaaS-first company.
• Competitive base salary plus performance bonuses.
• A supportive, inclusive, and entrepreneurial culture where your ideas are valued.

💡 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 and Inclusion at Olly Olly

At Olly Olly, we celebrate differences because diversity drives innovation, and your voice truly matters here. As we shape the future of small business growth together, it's important that we also comply with all U.S. employment eligibility laws. Before applying, be sure to have current, independent authorization to work in the United States and all I-9 required documentation. While we value every unique perspective, keep in mind that we're not able to offer employment visa sponsorship.