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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’re seeking a hands-on recruiting leader to rebuild, scale, and mature Olly Olly’s talent engine. This is not a “coach from the sidelines” role — it’s a player/coach position for someone eager to lead by example, actively jump into recruiting efforts, and simultaneously architect the systems, team, and processes needed to take our function to the next level.You’ll operate at the intersection of high-velocity sales recruiting and technical hiring, helping us build global teams from the ground up while setting a new standard for excellence in candidate quality, process efficiency, and business partnership.
This is a true builder role for someone who thrives in a scrappy, growth-stage environment and is ready to transform recruiting into a best-in-class, scalable function.
🚀 The Impact You’ll Have
- Org-Level Leadership: Own the full recruiting function — org design, team structure, processes, enablement, and performance.
- Strategic Workforce Planning: Partner with executive leadership on headcount forecasting, talent strategy, and workforce planning across sales, technical, and global contractor roles.
- Process & Infrastructure: Implement scalable recruiting systems, data-driven reporting, and best-in-class candidate experience standards.
- Team Development: Coach and develop the existing recruiting team while making strategic hires to expand capacity and capability.
- Compensation Strategy & Team Motivation: Partner with leadership to design and refine recruiter incentives, commission structures, and performance frameworks that motivate the team, reward impact, and scale with business goals.
- Cross-Functional Partnership: Align with RevOps, People Ops, and hiring managers to deliver predictable, high-quality talent pipelines across the business.
- Global Hiring & Compliance: Lead international contractor hiring strategy and ensure compliance across global jurisdictions.
- Executive Recruiting: Own leadership-level searches and key technical hires critical to Olly Olly’s SaaS and agency business units.
✅ What We Really Need From You
- 8+ years of senior recruiting experience, including 3+ years leading teams in a growth-stage SaaS or similar fast-paced company.
- Proven success scaling from 0 → 1 and transforming recruiting functions to support rapid growth.
- Deep experience in high-volume sales recruiting, technical hiring, and global contractor sourcing.
- Track record of balancing hands-on recruiting delivery with strategic leadership — able to both “roll up your sleeves” and design scalable systems.
- Strong executive presence with the ability to collaborate closely with executive leaders and influence company-wide talent decisions.
- Adept at building processes, reporting infrastructure, and recruiter performance frameworks that drive accountability and results.
- Comfortable operating in scrappy, fast-paced, resource-constrained environments where speed, creativity, and execution are critical.
- Excited by the opportunity to help shape compensation and incentive programs that align team motivation with business impact.
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What You'll Love About Working at Olly Olly
- Hybrid Environment: Perfect blend between in-office collaboration & WFH
- Monday - Friday 8AM-5PM CST schedule
- Work-life balance: Generous PTO, including 15 vacation days and U.S. holidays.
- Medical, Dental, and Vision Insurance
- 401(k) Retirement Plan
- Work with a profitable, debt-free company that's proven its model and is ready to scale
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Why Choose Us?
This is the rare opportunity to join a company that's already winning and help amplify that success. Your creativity, attention to detail, and passion for excellence will directly contribute to our first-ever marketing engine while supporting the growth of small businesses nationwide.This isn't just about following templates; it's about taking good content and making it great, then implementing it in ways that drive real business results for a company that's ready to unleash its full potential.🌈
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 small business growth.
