Director of Recruiting

Olly Olly • Austin, TX

89d

About The Position

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’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.

Requirements

• 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.

Responsibilities

• Own the full recruiting function — org design, team structure, processes, enablement, and performance.
• Partner with executive leadership on headcount forecasting, talent strategy, and workforce planning across sales, technical, and global contractor roles.
• Implement scalable recruiting systems, data-driven reporting, and best-in-class candidate experience standards.
• Coach and develop the existing recruiting team while making strategic hires to expand capacity and capability.
• 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.
• Align with RevOps, People Ops, and hiring managers to deliver predictable, high-quality talent pipelines across the business.
• Lead international contractor hiring strategy and ensure compliance across global jurisdictions.
• Own leadership-level searches and key technical hires critical to Olly Olly’s SaaS and agency business units.

Benefits

• Hybrid Environment: Perfect blend between in-office collaboration & WFH
• Monday - Friday 8AM-5PM CST schedule
• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Number of Employees: 251-500 employees