Executive Operations Assistant

About Recess

Recess is a modern, flexible childcare company built to meet the realities of today’s families. Unlike traditional childcare centers that rely on rigid full-time schedules, Recess offers flexible, fully-customizable schedules or on-demand drop-in care, along with thoughtfully designed classes and community programming for children and parents.

Our spaces are intentionally designed to be calm, safe, and developmentally appropriate, with a focus on quality supervision, consistency, and thoughtful programming rather than high-energy or high-risk activities. We serve children from infancy through early childhood, and we operate in a highly regulated environment where attention to detail, safety, and operational discipline matter deeply.

Recess currently operates two locations and is expanding in response to strong demand from families seeking more flexible, reliable childcare options. Our growth is driven by a clear need in the market and a commitment to building sustainable operations — not growth for growth’s sake.

As we open additional locations, maintaining operational consistency, strong internal systems, and a high bar for execution is critical. This role plays a key part in making that possible.

About the Role

Recess is seeking a highly organized, detail-oriented Executive Operations Assistant to support the CEO and Head of Programs across the administrative, operational, and people-related functions of a rapidly growing childcare company.

This role is foundational to Recess’s next phase of growth. The Executive Operations Assistant will help streamline internal processes, support hiring and onboarding, maintain documentation and training systems, and assist with facility-level operations across multiple current and future locations.

In addition, this role will serve as a rare, as-needed backup for childcare coverage within a facility when operationally required.

This position is ideal for someone who wants to be on the ground floor of a fast-growing business, contribute directly to how the company scales, and grow alongside the organization as new locations open.

Why This Role Matters

• Recess is actively expanding, and this role helps create the operational backbone that enables that growth.
• You will help ensure consistency, compliance, and stability across locations.
• This role offers meaningful growth potential as the company scales.
• You will work closely with leadership and have visibility into nearly every part of the organization.

Key ResponsibilitiesExecutive & Administrative Support

• Provide direct administrative support to the CEO and Head of Programs.
• Manage scheduling, calendars, documentation, and internal coordination.
• Maintain organized digital and physical records across operations, HR, and compliance.
• Draft, update, and manage internal documents, SOPs, training materials, and playbooks.
• Track action items and deadlines to ensure operational continuity as the company scales.

HR, Hiring & People Operations Support

• Draft and manage job postings for current and future locations.
• Screen resumes and conduct initial interviews.
• Coordinate interview scheduling and hiring logistics.
• Support new-hire onboarding, training coordination, and documentation.
• Maintain employee files and assist with compliance-related recordkeeping.
• Support ongoing training, certifications, and documentation across locations.

Facility & Operations Support

• Support operational oversight for multiple childcare locations.
• Assist with supplies ordering, inventory tracking, and vendor coordination.
• Coordinate utilities, maintenance, cleaning, and repair needs.
• Proactively flag operational risks and gaps as the organization grows.
• Help standardize systems and processes that support scalable operations.

Childcare Backup Support (Infrequent)

• Serve as occasional backup childcare support when staffing coverage requires it.
• Step in only when necessary to support ratios or short-term gaps.
• Follow all Recess policies, procedures, and safety standards.
• This is not a primary classroom role and will be used sparingly.

Required Qualifications (Mandatory)

• Prior experience in an administrative, executive assistant, operations, or property management role.
• Exceptional attention to detail and organizational skills.
• Strong written and verbal communication skills.
• Ability to manage confidential information with discretion.
• Comfort working in a regulated, compliance-driven environment.
• High reliability, accountability, and follow-through.

Preferred Qualifications

• Experience in childcare, education, or another regulated industry.
• Experience working with children from infancy through age six.
• Familiarity with HR workflows, onboarding, and training systems.
• Experience supporting founders or senior leadership teams.
• Comfort with documentation systems, shared drives, and internal tools.

Growth & Opportunity

• This role is designed to grow as Recess grows.
• Strong performers may take on expanded responsibility across operations, people systems, or multi-location support.
• You will be part of the early core team shaping how Recess operates at scale.

Job Types: Part-time, Contract

Pay: $18.00 - $22.00 per hour

Expected hours: 10 – 40 per week

Application Question(s):

• What interests you most about this position?
• Do you have any experience in childcare? If so, please elaborate.
• How far do you live from our locations in Northern Liberties, Philadelphia?
• Although most work can be done remotely, on-site visits and check-ins are required; additionally, you may be required to support staffing gaps if necessary (although expected to be rare). Please confirm your understanding of this job requirement.

Work Location: Hybrid remote in Philadelphia, PA 19123

Salary : $18 - $22