Senior Recruitment Specialist

Operations Manager - Customer Success and Strategic Support (Pupil Transportation)

Location - Remote

Starting Salary $67,500-70,500 Per Year

What’s in it for you (benefits will vary if not hired for full-time permanent):

Health insurance

PTO (120 hours accrued per year starting)

13 Paid company-wide Holidays

401k plan

An annual $250 stipend to support any home office needs

Competitive salary, commensurate with experience

Work in an inclusive, caring and values driven environment

Make a critical difference for children, families and educators

Weekly Hours: 40-55 Hours/Week

General Shift Hours:

Preferred standard schedule is approximately 9:00am-5:30pm Central Time to support Eastern, Central, and Western US time zones. However, specific hours will shift depending on business and coverage needs and could be an 8-9 hour shift anywhere from 6:00am Eastern Standard Time to 6:00pm Pacific Standard Time

We are seeking an

Operations Manager – Customer Success & Support

who will provide high-level leadership across our operations department. This person will join a high-growth, high-volume, fast-paced business and play a critical role in helping us to ensure exceptional daily service for hundreds of children and school districts, as well as a fulfilling and sustainable employment experience for drivers and supporting staff. This role carries responsibility for ensuring results in routing, dispatch, and customer success where assigned.

The Customer Success & Support Manager may be assigned to a geography, project, or function depending on business needs; for example, covering a region during an absence, strengthening routing performance within a particular geography, or leading escalations and follow-through with districts. This is a hands‑on leadership role requiring operational expertise, customer‑facing strength, and flexibility to step into high‑need areas. This role requires a strong leader who thrives in ambiguity, communicates clearly, and can quickly earn trust with staff, drivers, and district partners.

We are seeking a core values‑aligned, goal‑driven, and enthusiastic operations manager who is comfortable in a remote small business environment. This person should be a proven manager and team leader, have a high standard of excellence, strong analytical thinking, exceptional written and verbal communication skills, and a deep connection to our mission of providing access to opportunity for all students.

This position reports to the Director of Operations, and you will collaborate regularly with other managers, and the operations team as a whole. This role does not currently include direct reports but provides leadership, direction, and accountability across multiple teams.

Who you are:

A strong leader who is confident in giving direction and setting expectations, even without direct reports

Flexible and adaptable, thrives in environments where priorities shift daily

Customer‑focused, with strong relationship‑building skills and the ability to restore confidence following service issues

Ambitious and eager to grow within the company, open to taking on increasing levels of responsibility

Calm under pressure, detail‑oriented, and driven to deliver results and exceed metrics

Calm but urgent problem‑solver; sees solutions where others see problems

Strong attention to detail and impeccable follow through

Tech‑savvy and comfortable with navigating multiple online platforms

Energetic, enthusiastic connector who forms relationships and earns genuine trust quickly, even when working with a diverse, distributed team and customers

Role model the company core values and hold others accountable for doing the same; builds community across functional teams and roles

Able to exhibit our company competencies at the manager level (review by clicking here)

Travel required annually at a minimum, may be more to train new staff members or attend meetings with key district partners

What you’ll do:

Work closely with the Director of Operations to analyze data across the department and develop a weekly action plan to achieve ambitious goals, including fulfillment rate, on time arrivals, district and driver satisfaction, and more

Step into regions as needed to provide manager‑level leadership when a manager is out, the workload is high, or extra support is required

Provide direction, feedback, and accountability to assistants, coordinators, and specialists to ensure goals are met and customers are satisfied

Lead escalations during on‑call shifts with districts, guardians, or drivers, ensuring concerns are addressed promptly and relationships remain strong

Support routing and change requests when needed, ensuring new and existing student rides are implemented smoothly

Collaborate with other managers and the Director of Operations on strategic initiatives and process improvements

Support recruitment, screening, onboarding, and training of new Operations team members ranging from administrative assistants to managers

Model calm, solutions‑oriented leadership and coach staff through conflict resolution

Serve as a member of Operations Leadership Team, including contributing to department‑wide strategic plans and decision making, including critical budget and forecasting decisions/strategy

Required Qualifications

At least 5 years of relevant experience; at least 3‑5 years of leadership or management experience (ops, logistics, etc)

Bachelor’s Degree or higher in a relevant field

Strong written and verbal communication skills.

Proficiency with online platforms, data tracking, and remote team tools.

Demonstrated ability to provide feedback and coaching across levels.

Have a working computer with a camera and microphone

Have a reliable internet connection

Exhibits all competencies up to Manager (Application) level on Core Competencies

Ability to travel up to 30% of the time

Preferred qualifications:

Masters Degree in a relevant field

Strong knowledge of pupil transportation industry processes and regulations

High level routing and dispatching experience

Experience in customer service or account management

2+ year of full‑time remote work experience (remote experience related to COVID or hybrid do not meet this criteria )

Start date:

Negotiable within 2 weeks of offer

About Us:
At BuckledIn, we eliminate transportation as a barrier to children’s success. We do this by mobilizing outstanding adults who want to have a positive impact on children. Our drivers transport many school‑age students experiencing homelessness, living in foster care, living with mental or emotional special needs, or other circumstances that make traditional yellow school buses a poor transportation option. That’s where we come in.

We match each student with a part‑time driver who takes that student to and from school every day. Many of our drivers are current or former teachers, nurses, nannies, babysitters, personal caregivers, nursing home aides, social workers, parents, and grandparents who are eager to be a positive influence in their student’s lives.

Our values:
Excellence Everywhere -

We don’t settle—we set the standard. From safety to service, we exceed expectations to protect and support students at every turn.

Driven to Learn -

Curious, open‑minded, and always improving. We embrace feedback, seek new ideas, and grow so we can serve better every day.

Trust is Everything

- We earn trust through consistency, respect, and follow‑through. Our words and actions align, every time.

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