Transafe Transportation LLC Operations & People Engagement Lead Chestnut Hill, MA · Part time Company website

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About Us
Since 2019, Transafe Transportation LLC has provided safe, reliable, and caring student transportation giving peace of mind to towns, school districts, and families.
Headquartered in Brookline, Massachusetts, Transafe specializes in transporting Pre-K through 12th grade students to and from school and extracurricular activities, working closely with districts and families to ensure timely and safe transit. A WBE/MBE/SLBE-certified company, Transafe has proudly delivered thousands of rides to hundreds of vulnerable students with a zero major incident safety record.
We are not just transporting students...we are building trust, one safe, reliable ride at a time.

Equal Opportunity / Work Authorization
Transafe is an Equal Opportunity Employer and is committed to creating an inclusive workplace. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other legally protected characteristic. Applicants must be authorized to work in the United States.

Position Overview

The Operations & People Engagement Lead supports the day-to-day coordination of student transportation operations, with a focus on routing, family and school communication, recruiting support, training support, process documentation, and employee file administration. The role ensures routes are efficient, communication is timely, staffing needs are supported, and employee records are maintained accurately.

The Lead is a key point of contact for families, school partners, drivers, monitors, and job candidates. This is a part-time position intended to scale with the business.

Key Responsibilities

Routing & Transportation Coordination

• Help develop, maintain, and update safe and efficient transportation routes based on student addresses, school/program schedules, traffic patterns, and operational needs.
• Help review and adjust routes in response to absences, new enrollments, address changes, school updates, or other operational changes.
• Help communicate route details — pick-up and drop-off times and locations — to families and 7D transportation staff.

Family, School & Community Communication

• Serve as a primary point of contact for families regarding transportation questions, concerns, and service updates.
• Communicate transportation delays, route changes, or service issues to families and school administration in a timely and professional manner.
• Support positive relationships with schools, families, drivers, and monitors.

AI-Dispatch Exception Handling (SY2026–27 onward)

• Serve as the human exception layer for the Transafe App's AI-driven dispatch and parent-notification system.
• Handle direct phone calls from parents who do not use smartphones or who need personal assistance beyond automated notifications.
• Monitor AI-generated communications for tone and accuracy; flag issues to the CEO for system correction.
• Triage and resolve day-to-day operational exceptions that fall outside the automated workflow.

Client Account Ownership

• Primary account owner for private-family clients (monthly subscription and one-off).
• Maintain personal relationships with private families; serve as their first point of contact.
• Partner with the President & COO on private-client retention and renewal (95%+ renewal target).

Recruiting, Training & Employee Support

• Coordinate recruiting activities for drivers and monitors: job postings, candidate follow-up, interview scheduling, and onboarding support.
• Support employee onboarding and offboarding in Gusto; maintain accurate personnel records.
• As a certified 7D trainer, help deliver Transafe University training; maintain training documentation and records.
• Own driver engagement activities: recognition programs, one-on-one check-ins, and culture initiatives.
• Update and maintain electronic employee and operational files.

Process Documentation & Administrative Support

• Help document, organize, and maintain SOPs, process guides, checklists, and internal guidelines for key responsibilities.
• Support efforts to standardize recurring workflows across routing, communication, recruiting, onboarding, training, and recordkeeping.
• Help identify opportunities to improve administrative and operational consistency; escalate recommendations as appropriate.
• Support general transportation operations, employee coordination, and administrative duties as assigned.

Success Measures

Performance in this role is measured against the following, tied to the company's Strategic Plan:

• Talent & Culture: Support hiring to 20 certified 7D drivers by Aug 1, 2026
• Talent & Culture: Driver retention: 85%+
• Customer Experience: 100% ride-confirmation, turnaround & parent-comm standards
• Customer Experience: Private-client renewal: 95%+
• Compliance & Risk Management: 100% employment and training files audit-ready
• Family communication response time: within 24 hours during business days

Qualifications

• Valid driver's license, 7D certificate, and 7D Training Certification required.
• 3+ years of experience in 7D student transportation, operations, customer service, recruiting coordination, office administration, or a similar role required.
• Comfort with computers and digital systems (apps, email, spreadsheets, shared files).
• Experience communicating with families, schools, students, and employees in a professional and service-oriented manner.
• Experience with scheduling, routing, onboarding, training coordination, file management, or process documentation is a plus.
• Ability to maintain confidentiality and handle sensitive employee or family information with care.

What We're Looking For

• Warm, personable, and professional with strong relationship-building skills.
• Organized and dependable, with the ability to manage multiple moving parts.
• Comfortable learning new systems and taking on increasing responsibility over time.
• Clear communicator who can work well with families, schools, employees, and candidates.
• Detail-oriented and able to keep records accurate and up to date.
• Able to create structure and document processes clearly and practically.
• Process-minded, with an eye toward consistency, efficiency, and continuous improvement.
• Positive, resourceful, and calm under changing operational conditions.
• A team player willing to grow with the business and support evolving needs.

Hours

Approximately 35 hours per week, Monday through Friday. Hours may vary slightly based on operational needs but should remain below 40 per week unless otherwise approved.