Title: Personal Assistant / Office Manager

Reports To: CEO (Dom Di Pietro)

Salary: $55,000 – $65,000/year (base, with potential performance bonus)

Location: In-office (Millersville Md, & be able to travel to Edgewater, Md on a weekly basis)

Role Purpose:

This role exists to maximize the CEO’s time and productivity by handling personal and low-value business tasks, logistics, errands, and company culture initiatives. The PA works closely with the Chief of Staff to ensure all high-priority and judgment-heavy matters are escalated appropriately, while managing day-to-day execution independently.

Key Responsibilities:

1. Personal Logistics & Life Admin

Manage CEO’s personal calendar, family scheduling, and appointments
Handle personal travel bookings (flights, hotels, cars) with CEO approval
Coordinate personal errands, deliveries, and vendor relationships
Run errands in-person, including trips to CEO’s home, other properties, or locations as assigned
Maintain confidentiality and discretion for all personal matters

2. Business Support & Operations

Support CEO during podcasts, content creation, and media events (setup, filming assistance, photos/videos)
Handle low-level business tasks delegated by CEO (scheduling, travel logistics, minor vendor coordination)
Support property and business operations by visiting locations as requested
Perform ad hoc research, document collection, and follow-ups

3. Company Culture & Events

Plan and coordinate company events, celebrations, and team-building activities
Assist with culture initiatives to maintain employee engagement and morale
Coordinate logistics, invitations, venues, catering, and event execution

4. Collaboration with Chief of Staff

Route judgment-heavy items to CoS for prioritization and escalation
Work independently on low-value tasks that do not require CoS review

5. Communication & Availability

Full-time, in-office role with occasional flexibility for errands or events
Available for texts or calls from CEO during business hours and occasionally on weekends
Pre-approval required for significant purchases or major decisions

Skills & Traits Required:

Extremely organized, reliable, and detail-oriented
Comfortable managing personal and business logistics
Able to handle multiple projects and priorities simultaneously
Tech-savvy, including experience with scheduling, travel booking, content setup, and office software
High level of discretion and confidentiality
Strong communication skills, proactive attitude, and willingness to “do what it takes”
Comfortable driving to multiple properties and running errands in-person
Flexible, adaptable, and able to anticipate CEO needs
Comfortable assisting with content creation or coordinating setup when needed
Experience planning events, coordinating vendors, or managing company culture is a plus
College degree preferred

Authority & Boundaries:

Executes tasks independently where low judgment is required
Escalates judgment-heavy items to CoS
Works closely with CEO on tasks that can be handled directly between PA and CEO
Does not make high-level strategic decisions independently without pre-approval

Measures of Success:

CEO’s time protected and low-value tasks consistently executed flawlessly
Personal errands, property management, and logistics completed accurately and on time
Company events and culture initiatives planned and executed successfully
Effective collaboration with CoS to escalate appropriate items and reduce CEO cognitive load
Positive feedback from CEO, leadership team, and content creators
Proactive anticipation of needs without repeated direction

Job Type: Full-time

Pay: $55,000.00 - $65,000.00 per year

Benefits:

Paid time off

Application Question(s):

Have you previously supported an executive, founder, or senior leader in a high-trust support role (personal assistant, executive assistant, operations support, etc.)?
This role requires availability during business hours and occasional evenings or weekends as needed. Are you able to meet this expectation?
This is a full-time, in-office role that requires running in-person errands and visiting multiple properties. Do you have reliable transportation and the ability to commit to this schedule?
Are you comfortable managing both personal and business logistics for a CEO, including confidential and private matters?

Work Location: In person

ROI Construction

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