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 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 We Are
Our lean Legal & Compliance team takes pride in operating as a high-trust, directly embedded partner to the business. We are a broad-scope, fast-moving team dedicated to building scalable tracking systems, protecting the company, and accelerating operations through the deliberate use of AI-forward legal tools.
We do, and you will, support the business through the following responsibilities:
- Contract Queue Management: Manage the contract review queue end-to-end, including first drafts, redline cycles, counterparty coordination, and signature tracking.
- Agreement Drafting: Draft and redline standard agreements, including NDAs, vendor contracts, SOW amendments, and service contracts.
- Repository & Template Ownership: Maintain the contract repository within the CLM system and ensure the template library remains current and retrievable.
- Lifecycle Tracking: Proactively flag upcoming contract renewals, key dates, non-standard terms, and counterparty obligations.
- Intake & Matter Triage: Triage incoming legal requests, route matters to the appropriate team members, and monitor compliance with contractual SLAs.
- Litigation Support & Holds: Coordinate document preservation notices, oversee litigation hold requests, track custodian compliance, and support discovery.
- Legal Proceeding Operations: Manage court filings, deadline calendaring, and procedural compliance for garnishments and external information requests.
- AI & Workflow Optimization: Utilize specialized generative AI tools to accelerate legal research, draft summaries, and continuously optimize team workflow efficiency.
Who You Are
You are a sharp, process-oriented legal professional who thrives in a growth-stage environment and takes genuine pride in operational excellence. You are an independent self-starter who can navigate ambiguity, build workflows from scratch, and ensure zero critical legal deadlines are missed.
You bring the following essential experiences and mindsets to our team:
- Professional Paralegal Experience: 4–6 years of dedicated paralegal experience within a law firm or fast-growing company managing significant volume.
- Commercial Contracting Skills: Proven ability to draft, review, and redline contracts (NDAs, vendor agreements, SOWs) with high attention to detail.
- Systems Expertise: Hands-on experience navigating and managing legal operations within Ironclad or an equivalent modern CLM system.
- Matter Tracking Proficiency: Demonstrated success managing legal intake systems and balancing high-volume workstreams with competing deadlines.
- Litigation & Discovery Competency: Experience executing litigation holds, managing discovery coordination, and overseeing court filing timelines.
- Regulated Industry Exposure: Background working within a highly regulated environment, such as transportation, education, healthcare, or similar.
- Technical & AI Adaptability: A tech-forward mindset with an active interest in experimenting with AI drafting assistance and research automation tools.
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 in Los Angeles, CA is $80,000.00 - $95,000.00. 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 is a fully remote role. Candidates must reside in and perform work from 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, or WI. We are not currently considering candidates who will perform work from any other state.
Skills Required
- 4-6 years of dedicated paralegal experience within a law firm or fast-growing company
- Proven ability to draft, review, and redline contracts (NDAs, vendor agreements, SOWs)
- Hands-on experience navigating and managing legal operations within Ironclad or an equivalent modern CLM system
- Experience executing litigation holds, managing discovery coordination, and overseeing court filing timelines
- Background working within a highly regulated environment, such as transportation, education, healthcare, or similar
- A tech-forward mindset with an active interest in experimenting with AI drafting assistance and research automation tools
What the Team is Saying
HopSkipDrive Compensation & Benefits Highlights
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Healthcare Strength — Corporate roles include medical, dental, vision, HSA/FSA options, mental‑health resources/EAP, and short‑ and long‑term disability. Paid parental leave is explicitly included within the health and wellbeing offering.
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Leave & Time Off Breadth — Employees are offered flexible or generous PTO, paid holidays, and a company‑wide end‑of‑year closure, with sick time also available for employees and families. Feedback suggests the remote‑first setup further supports time away when needed.
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Equity Value & Accessibility — Equity is provided to full‑time employees and positioned as a standard part of compensation. Feedback suggests this ownership component meaningfully augments total rewards for corporate roles.
HopSkipDrive Insights
What We Do
We help get students to their destinations, safely and on time. Our technology connects school partners to a network of highly vetted drivers with small vehicles and wheelchair-accessible vehicles, complementing the yellow bus, filling in gaps, and enabling schools to support student transportation needs. Our partnerships with school districts, child welfare agencies and nonprofits ensure equitable educational access for our most vulnerable populations, including youth in foster care, youth experiencing homelessness, and youth with special needs.
Why Work With Us
HopSkipDrive exists to create opportunity for all through mobility. As the leader in innovative, supplemental school transportation, we’re taking a different approach to addressing inequities in educational access that are affecting millions of kids each day. We’re paving the way for a future where every student has the chance to succeed.
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HopSkipDrive Offices
Remote Workspace
Employees work remotely.
HopSkipDrive’s headquarters is located in Los Angeles’ Little Tokyo district and we love this space! However we believe strongly that most roles allow for a remote-first approach to work, and most of our employees work remotely.
