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 over 20states. 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 use AI every day, and not as a productivity add-on. It's woven into how we work at every level. We're rethinking how work gets done, who does what, and what a small team can accomplish. If you've already built AI into how you work, you'll hit the ground running. If you haven't, you'll need to be ready to learn fast and work differently than you have before.

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, then build, implement, and iterate on the solutions.
• Embed AI into day-to-day recruiting operations: use AI tools to draft job descriptions, prepare interview kits, synthesize candidate feedback, build offer comps, and generate pipeline analytics.
• Build a repeatable process for staying current on the recruiting technology landscape and bringing forward-looking recommendations to leadership.

Elevate Stakeholder Experience & Internal Partnership

• Deliver a white-glove experience for hiring teams: proactive communication, structured intake processes, regular pipeline updates, and clear feedback loops with every hiring manager.
• Present recruiting data, insights, and recommendations to senior leaders with confidence and clarity — including when the data tells a story they need to hear.
• Coach hiring managers on effective interviewing practices, bias mitigation, and decision-making rigor — especially in panels with varied experience levels.

Own Data, Insights & Continuous Improvement

• Build and maintain recruiting dashboards using tools like Claude, Omni, etc.
• Use data to drive decisions — identify bottlenecks, test hypotheses, and make evidence-based recommendations on where to invest recruiting effort and resources.

• Champion and model a culture of continuous improvement: regularly bring process innovations, lessons learned, and market intelligence back to the team.

What you’ll bring

• 6+ years of talent acquisition experience in fast-paced tech environments, with a proven track record of managing full-cycle recruiting across the organization. Experience recruiting for GTM roles is required
• An AI-native builder mindset: you don’t just use tools, you ship automations and design intelligent workflows to eliminate manual overhead and scale operations.
• Expertise in running high-velocity, outbound-heavy operations — from sophisticated cold outreach to closing complex leadership roles.
• A systems-thinking approach: you take full accountability for the candidate journey, balancing speed and scale with an unyielding bar for quality.
• Proven ability to operate as a strategic partner to leadership, combining structure, sound judgment, and the courage to challenge assumptions.
• A deep interest in AI research and the broader technology ecosystem, with a drive to translate market trends into better talent processes.
• As a high-ownership executor and innovator, you will own the talent function—including systems and data—while serving as a key strategic partner to the Senior Director, People & Talent.

Our Investment In You

We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role is 125,000 - 145,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.

HopSkipDrive is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.

**This role will be fully remote in one of the following states AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI** Prioritizing candidates in Eastern and Southeast states based on business needs.