IT Specialist

At HopSkipDrive, our goal is to create opportunity for all through mobility.

We’re a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. Through our marketplace, we connect kids, older adults, or anyone needing extra support to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts around 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 17 states around the country. We continue to expand at a rapid pace, making the Inc. 5000 list four times, as well as the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M in funding to date.

Who We Are

Our Information Technology team functions as a critical partner in scaling HopSkipDrive, building a secure and efficient technology ecosystem. We take pride in leveraging modern tools like automation and AI to empower every team member to do their best work. We do, and you will, support the business through the following responsibilities:

• End-User Support & Lifecycle Management: Provide day-to-day technical support (hardware, software, network) and manage the full device lifecycle (procurement, configuration, maintenance) for Mac and Windows environments.

• Automation & Optimization: Build, maintain, and optimize automation workflows using Zapier, Workato, and Google Apps Script to streamline IT operations and business processes.

• SaaS & Identity Administration: Administer Google Workspace and identity platforms (Okta, JumpCloud), including user provisioning, security settings, and leveraging AI-powered features.

• Infrastructure & Security: Collaborate on IT projects (system upgrades, migrations), maintain security best practices, and ensure compliance with company policies.

• Asset Management: Manage asset inventory and coordinate equipment orders for new hires, replacements, and remote workforce needs.

• Collaboration: Serve as a technical liaison for cross-functional teams to implement solutions and support communication tools (Zoom, Slack, Email).

• Availability: Provide after-hours support for critical incidents as needed and participate in periodic in-office travel to our Los Angeles headquarters.

• Who You Are

You are a strategic IT Specialist driven by a passion for leveraging the latest technologies (e.g., automation, AI) to build, engage, and scale a high-performing IT department. With the following skills, you will make a tangible and immediate impact, propelling our growth in the technology/SaaS landscape:

Skills and Experience:

• Experience: 5+ years of hands-on IT support or systems administration experience, preferably in a startup or high-growth environment.

• Technical Mastery: Proven ability to troubleshoot hardware and software issues in macOS and Windows environments, with strong experience in Google Workspace administration.

• Automation Specialist: Demonstrated experience building and managing automation workflows using tools like Zapier, Workato, or scripting languages (Python/Google Apps Script).

• Identity Management: Solid understanding of IAM concepts with practical experience managing tools like Okta or JumpCloud.

• Communication: Excellent verbal and written skills, with the ability to translate complex technical concepts for non-technical users and engage confidently with all employee levels.

• Project Ownership: Strong organizational skills with a proactive approach to problem-solving and the ability to manage multiple priorities independently.

• Customer Focus: A service-oriented mindset dedicated to resolving issues quickly to keep our teams moving.

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 $95,000 - $120,000. 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, CT, 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**