Strategic Talent Lead

About HopSkipDrive

At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation. Through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.

Founded by three moms as a solution to their own transportation challenges, we've now facilitated more than five million rides across over 20 states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date.

How we work

We're an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don't expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward.

We're remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar.

Who you are

We're looking for a Strategic Talent Lead who operates as a strategic partner, a process architect, and an AI-powered change agent, all at once. This is not just a fill-the-req role.

You will own the transformation of how HopSkipDrive identifies, attracts, and hires top talent. That means rethinking our processes from the ground up — cutting manual work, embedding AI tools where they drive real leverage, and building a recruiting experience that reflects the innovative company we are. You'll be the person who hiring managers trust most to build their teams, and the bar for who we hire and how we hire across the board.

You're a fast-paced, strategic recruiter who leads with data and thinks in systems. You're energized by the challenge of transforming a talent function — not just running it. You see process gaps as design opportunities. You use AI tools as a matter of course, not as a novelty. And you hold yourself to a high bar for the quality of the candidate and hiring manager experience you deliver.

You bring intellectual curiosity, critical thinking, and a strong point of view — and you're equally comfortable presenting recommendations to leadership, coaching a first-time hiring manager, or digging into an ATS audit because you spotted an inefficiency that's costing you pipeline velocity. You move fast and bring others with you.

What you'll do

Drive Talent Strategy & Pipeline

• Own full-cycle recruiting across functions from intake through close with a consistent bar for quality, speed, and candidate experience.
• Build and execute strategic, customized sourcing strategies that go well beyond job boards: including talent mapping, competitive intelligence, community-based sourcing, and warm pipeline development.
• Serve as a trusted advisor to hiring managers and senior leaders on role design, competency definition, interview architecture, and offer strategy.
• Manage and continuously optimize our use of Greenhouse (ATS) to ensure data integrity, pipeline visibility, and reporting accuracy across all active searches.
• Own the recruiting tech ecosystem: assess platforms against market standards and lead strategy for any future system migrations.

Lead AI-Forward Process Transformation

• Audit our current recruiting workflows end-to-end and identify where manual processes can be eliminated, automated, or AI-enhanced.