IT Specialist, HopSkipDrive
$95-120k
Plus equity stock options
More information about location
Safe youth transportation solution
Job no longer available
Safe youth transportation solution
501-1000 employees
Job no longer available
$95-120k
Plus equity stock options
More information about location
501-1000 employees
Company mission
To create opportunity for all through mobility.
Role
Who you are
- 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
What the job involves
- 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
Our take
Across the US, school transportation is under pressure as driver shortages, budget cuts, and rigid bus routes are making it harder for students to get to school safely and on time. This has opened the door for smaller vehicles and ride-hailing services to step in and support those students who don't fit neatly into traditional routes. HopSkipDrive has grown within this space, offering a flexible alternative that helps schools fill these gaps.
HopSkipDrive connects children with carefully vetted caregivers (often grandparents, nurses or childcare processionals) who then provide reliable rides when buses or public transport falls short. Operating in 17 states and supporting over 10,000 schools, the services has certainly eased commutes for many families.
And now the company is focsued on strenghtening its impact with technology and innovation. With its RouteWise AI platform it helps districts cut costs, improve efficiency and manage driver shortages, all while new safety modules and AI-driven planning tools continue to raise industry standards. With these advancements and a growing network of partners, the company is ready to keep shaping a more flexible futur for school transportation.
Freddie
Company Specialist at Welcome to the Jungle
Insights
23% employee growth in 12 months
Company
Funding (last 2 of 7 rounds)
Sep 2022
$37m
SERIES D
Aug 2021
$25m
SERIES C
Total funding: $107m
Company benefits
- Medical, Dental & Vision
- Health Spending Account
- Mental Health Resources
- Employee Assistance Program
- Short- & Long-Term Disability Insurance
- Paid Parental Leave
- 401K Plan
- Company Ownership/Equity
- Medical & Dependent Care FSA
- Travel Insurance
- Supplemental Legal
- Fully Remote Work Option
- Flexible Time Off
- 11 Annual Paid Holidays
- Week Closure at End of Year
- Sick Time Off for You and Family
- Home Internet Reimbursement
- Professional Development & Learning Stipend
- Remote & In-Person Quarterly Team Events
- Internal Rewards & Recognition Program
- Employee Referral Bonuses
Company HQ
Little Tokyo, Los Angeles, CA
Leadership
Joanna McFarland
(Co-Founder & CEO)Former Board Member at the Marketplace Industry Association and LA Tech.org.
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