Assistant Project Manager – Owner's Representative

O'Leary Group | New York, NY | Full-time

As part of our review, we ask candidates to complete a short application so we can learn more about your experience and how you approach real project situations.

About O'Leary Group

O'Leary Group is an owner's representative and construction project management firm. We act as advocate and advisor for ambitious businesses building commercial, hospitality, retail, wellness, and medical spaces, protecting their budget, timeline, and decision-making from planning through opening day.

The Opportunity

O'Leary Group is seeking an Assistant Project Manager to support the planning and delivery of multiple real estate development and construction projects while developing the experience and judgment required to lead projects independently over time.

You will work closely with OLG Project Managers and directly with clients, architects, contractors, consultants, and vendors to coordinate project information, maintain project controls, track decisions and deliverables, and help keep projects organized and moving forward.

The Project Manager retains overall accountability for the project, while the APM takes direct ownership of assigned project controls, coordination, documentation, and follow-through.

A strong APM anticipates what is needed, keeps work moving, and raises questions or risks early. Over time, you will be expected to build a broader understanding of how project decisions affect budget, schedule, quality, risk, and the client's overall objectives.

This is a role for someone who wants to develop into a strong project manager, not simply perform project administration.

What You Will Own and Support

Project Controls & Coordination

• Take direct ownership of assigned project controls, trackers, deliverables, and coordination activities.

• Maintain accurate and current project information across OLG's project management systems.

• Track decisions, responsibilities, deadlines, approvals, and open items and follow through to keep work moving.

• Coordinate with architects, contractors, consultants, vendors, clients, and teammates to obtain required information and resolve outstanding items.

• Recognize when missing information or delayed actions could affect broader project objectives.

Schedule & Planning

• Support the development and maintenance of project schedules, milestones, and decision timelines.

• Track upcoming deadlines and dependencies and help ensure required actions occur in advance of them.

• Identify inconsistencies, missing inputs, or potential schedule concerns and raise them early.

• Develop an understanding of how individual activities and decisions affect the broader project schedule.

Budget & Cost Management

• Support maintenance of project budgets, commitments, forecasts, invoices, change orders, and related cost information.

• Review documentation for completeness, accuracy, and consistency before it moves forward.

• Track outstanding financial items and required approvals.

• Identify discrepancies or information that requires additional review.

• Build an understanding of the financial implications of project decisions.

Documentation & Communication

• Prepare meeting materials, project updates, logs, reports, and other project documentation.

• Capture decisions, responsibilities, and next actions accurately.

• Maintain project records so information is organized, current, and accessible.

• Communicate professionally and clearly with clients and project partners.

• Follow through on assigned communications and outstanding information.

Procurement & Deliverables

• Support procurement activities, vendor coordination, proposal tracking, approvals, and project deliverables.

• Track required information and deadlines across multiple parties.

• Help ensure deliverables are complete and appropriately documented.

• Identify gaps, conflicts, or delays requiring attention.

Problem-Solving & Developing Judgment

• Look beyond the immediate task to understand why the work matters to the project.

• Identify missing information, dependencies, inconsistencies, and emerging risks.

• Gather the relevant facts and context before raising an issue.

• Develop thoughtful possible next steps rather than simply identifying that something is wrong.

• Ask questions when context or direction is unclear.

• Build judgment about what can be advanced independently and when another perspective is needed.

Site & Construction Support

• Participate in site visits and construction meetings as required.

• Document observations, decisions, responsibilities, and follow-up items.

• Track field-related issues through resolution.

• Build familiarity with how design documents, construction activities, schedules, budgets, and field conditions interact.

What Success Looks Like at OLG

Performance in this role is measured by both the quality of your work and the judgment, reliability, and ownership you develop over time.

Set Realistic Expectations and Communicate Systematically

A strong Assistant Project Manager:

• Keeps assigned project information accurate, current, and organized.

• Communicates changes, missing information, or potential issues early.

• Follows through consistently on commitments and open items.

• Documents decisions and responsibilities clearly.

• Understands deadlines and raises concerns before a commitment becomes unrealistic.

• Provides others with reliable information they can use to make decisions.

Be Dedicated to Our Partnerships

A strong Assistant Project Manager:

• Is prepared, responsive, reliable, and professional.

• Builds trust with clients, teammates, and project partners through consistent follow-through.

• Understands that the quality and timeliness of their work affect other people on the project.

• Treats client information, time, money, and priorities with care.

• Communicates directly and respectfully when information or action is needed.

• Contributes to a project environment where people can rely on one another.

Be Thoughtful Planners and Innovative Problem-Solvers

A strong Assistant Project Manager:

• Looks ahead instead of focusing only on the task immediately in front of them.

• Understands the purpose behind assignments and how they connect to the larger project.

• Identifies missing information, risks, dependencies, and inconsistencies.

• Investigates issues and develops possible next steps.

• Asks thoughtful questions that demonstrate increasing project understanding.

• Builds judgment about what can be handled independently and when input is appropriate.

• Learns from experience and applies that learning to future work.

How This Role Develops

The APM role is intended to build the capabilities required to manage projects independently. Development is demonstrated not simply by completing more tasks, but by progressively:

• Understanding a larger portion of the project.

• Anticipating what will be needed.

• Recognizing risk earlier.

• Exercising stronger judgment.

• Taking greater ownership of project decisions and coordination.

• Developing confidence in client-facing situations.

• Connecting project details to budget, schedule, risk, and client objectives.

The progression from APM to Project Manager is ultimately a progression from owning defined components of a project to maintaining a clear view of the project as a whole and taking responsibility for its day-to-day outcome.

Qualifications

The successful candidate will bring relevant exposure to real estate development, construction, architecture, engineering, project management, or a related field and demonstrate the potential to grow into broader project ownership.

Experience and Requirements

• Bachelor's degree in Construction Management, Engineering, Architecture, Design, or a related field, or equivalent professional experience.

• Approximately 2–5 years of relevant experience in construction management, general contracting, architecture, engineering, design, development, or owner-side project management.

• Experience supporting commercial construction, renovation, or interior build-out projects.

• Foundational understanding of construction sequencing, budgets, schedules, procurement, and project documentation.

• Ability to read and interpret architectural drawings; familiarity with structural and MEP drawings is preferred.

• Strong written and verbal communication skills.

• Excellent organization, documentation, prioritization, and follow-through.

• Ability to manage multiple assignments and deadlines without losing sight of important details.

• Strong analytical and problem-solving skills.

• Proactive and resourceful working style.

• Comfortable asking thoughtful questions when additional context or direction is needed.

• Ability to work independently while collaborating closely with Project Managers and the broader OLG team.

We Also Value

• Strong organizational skills and attention to detail.

• Curiosity and an interest in understanding how projects work.

• Reliability and consistent follow-through.

• Analytical thinking and willingness to investigate inconsistencies.

• Ability to accept feedback and apply it quickly.

Technology

Candidates should be comfortable learning and working across modern project-management platforms. Experience with the following is helpful:

• Bluebeam

• Smartsheet

• Microsoft Project or similar scheduling software

• Procore or comparable construction-management platforms

• Microsoft Excel

• AI-enabled tools used to improve project documentation, analysis, and communication

Experience with every platform listed is not required. Strong organization, construction knowledge, communication, and the ability to learn new systems are more important.

Location & Travel

• Full-time position based in New York City.

• Requires regular attendance at client meetings, project sites, and OLG team meetings.

• Travel outside New York will be required depending on project assignments.

Compensation

• Anticipated base salary range: $70,000–$100,000

• Final compensation should reflect the candidate's relevant experience, capabilities, and demonstrated level of project responsibility.