Strategic Talent Lead

About HopSkipDrive

HopSkipDrive's mission is to create opportunity for all through mobility. The company is the leader in safe, fast, and simple supplemental student transportation, connecting kids to highly-vetted caregivers through their marketplace and solving transportation challenges for schools and school districts nationwide. Founded by three moms, they have facilitated more than five million rides across over 20 states, earned spots on the Inc. 5000 and Deloitte 500 Fast-Growing Technology lists, and raised $100M to date as a Series D company.

How We Work

AI is woven into how we work at every level—not as a productivity add-on but as a core part of rethinking how work gets done, who does what, and what a small team can accomplish. Candidates who have already built AI into their workflow will hit the ground running; others must be ready to learn fast and work differently.

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. This role owns the transformation of how HopSkipDrive identifies, attracts, and hires top talent—rethinking processes from the ground up, cutting manual work, embedding AI tools where they drive leverage, and building a recruiting experience that reflects the company's innovative culture. You'll be the hiring manager's most trusted partner for building teams, setting the bar for who and how we hire.

You are a fast-paced, strategic recruiter who leads with data and thinks in systems. You're energized by transforming a talent function—not just running it. You see process gaps as design opportunities, use AI tools as a matter of course, and hold yourself to a high bar for candidate and hiring manager experience. You bring intellectual curiosity, critical thinking, and a strong point of view—comfortable presenting recommendations to leadership, coaching first-time hiring managers, or digging into an ATS audit when you spot inefficiencies. 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 consistent quality, speed, and candidate experience. Build and execute strategic, customized sourcing strategies beyond job boards—including talent mapping, competitive intelligence, community-based sourcing, and warm pipeline development. Serve as trusted advisor to hiring managers and senior leaders on role design, competency definition, interview architecture, and offer strategy. Manage and continuously optimize Greenhouse (ATS) to ensure data integrity, pipeline visibility, and reporting accuracy. Own the recruiting tech ecosystem: assess platforms against market standards and lead strategy for future system migrations.
• Lead AI-Forward Process Transformation: Audit recruiting workflows end-to-end and identify where manual processes can be eliminated, automated, or AI-enhanced; build, implement, and iterate on solutions. Embed AI into day-to-day 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 bring forward-looking recommendations to leadership.
• Elevate Stakeholder Experience & Internal Partnership: Deliver a white-glove experience for hiring teams with proactive communication, structured intake processes, regular pipeline updates, and clear feedback loops. 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.

Benefits

• Equity for every full-time employee
• Flexible vacation
• Medical, dental, vision, and life insurance
• 401(k)
• FSA
• Opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential

Pay

The salary range for this role is $125,000 - $145,000. This position is remote and compensation will ultimately be in line with the location in which the position is filled. Final compensation will be determined by factors such as relevant work experience, skill set, certifications, and specific work location. The total compensation package also includes equity stock options.

Schedule

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.