Site Operations Assistant (Entry-Level – Training Provided)

Other Jobs To Apply

Job Title:

Site Operations Assistant (Entry-Level – Training Provided)
Hybrid | Field-Based – Chicago Area

Company:

Crawford Construction Corp.
Location: Chicago, IL – Local travel to project sites required
Schedule: Part-Time to Full-Time (Flexible)
Pay: $20–$24/hour (based on experience)
Perks: Includes Gas Allowance + On-the-Job Training

Position Summary:

Are you looking to get into the world of construction, real estate, and development—but don’t know where to start? This is your opportunity.

Crawford Construction Corp. is hiring a Site Operations Assistant to support our field and property development team across active projects in the Chicago area. This entry-level role includes full training, hands-on support, and the chance to grow with a company that’s reshaping neighborhoods through renovation, new builds, and community investment.

You’ll learn how jobs are coordinated from pre-walkthroughs to final inspections, and play a key role in organizing sites, managing documentation, and assisting with permit runs and vendor coordination.

You’ll be working closely with:

  • The Director of Development (Curtis Jones), overseeing layouts and scopes
  • The CEO (Katrice Crawford), managing progress, compliance, and growth goals
  • Our Field Technicians, Inspectors, and Vendors, making sure jobs stay on track
  • The Office/Operations team, reporting field notes and updates via Slack & Monday.com

This is a launchpad position with built-in growth. Past assistants have advanced into roles like Project Manager, Field Coordinator, or Construction Layout Planner within 6–12 months.

What You’ll Do:

  • Assist with site walk-throughs, vendor check-ins, and post-job punch lists
  • Confirm measurements, access, and basic scopes of work
  • Help with permit pickups, city inspection scheduling, and site readiness
  • Track deliveries, sourcing, and light material organization
  • Capture and upload before/during/after photos using tools like Pruvan
  • Submit updates and notes in Slack, Monday.com, or internal folders
  • Occasionally run errands to pick up tools, permits, or supplies

What We’re Looking For:

  • You’re punctual, self-motivated, and eager to learn by doing
  • Comfortable working at construction and renovation job sites
  • Can follow checklists, meet deadlines, and communicate clearly
  • Have a working smartphone, a reliable car, and know your way around Chicago
  • You enjoy solving problems and helping things run smoother
  • Bonus: Any experience with building trades, delivery runs, or coordination

What You’ll Gain:

  • Real-world exposure to renovation, flips, layout design, and permitting
  • A chance to grow into Project Coordinator or Field Supervisor roles
  • One-on-one time with leadership and a voice on how jobs are executed
  • Professional experience that translates to construction, development, or real estate careers
  • A purpose-driven team that’s transforming South Side homes and communities

How to Apply:

Send a short note introducing yourself and attach your resume (if available) to:
Email: resumes@crawfordconstructioncorp.net
Subject Line: Site Operations Assistant – Chicago

Optional: Include a short voice memo or video intro — especially if you're new to the field but excited to break in. We value drive over credentials.

Job Types: Full-time, Part-time

Pay: $20.43 - $28.00 per hour

Expected hours: 20 – 40 per week

Benefits:

  • Paid time off

Work Location: Hybrid remote in Chicago, IL 60615

Back to blog

Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...