Construction Project Lead, 2 Hour Learning (Remote) - $100,000/year USD

Crossover; Chicago (IL); On-site; USD 85,000 - 115,000; Full time

Job summary

2 Hour Learning in Chicago seeks a Construction Project Lead to coordinate on-site builds, enforce schedules, and use AI tools to accelerate planning and execution.

You will manage contractors, track milestones, and resolve sequencing issues across national projects, traveling about 60% and ensuring timelines stay on track.

Qualifications

• Direct experience executing U.S. construction projects, including on-site coordination or schedule enforcement.
• Experience owning a project timeline, tracking milestones, enforcing deadlines, and recovering from delays.
• Proficiency with digital project-management tools (Procore, Asana, MS Project) for tasks and documentation.

Responsibilities

• Coordinate on-site construction activities with contractors to ensure correct sequence and schedule.
• Own and enforce project timelines, track milestones, identify risks early, drive corrective action.
• Use AI tools to accelerate planning, documentation, and decision-making, reducing manual work and improving speed.

Skills

On-site coordination

Timeline ownership

Risk identification

AI tools usage

Contractor management

Tools

Procore

Asana

MS Project

Job description

Most construction roles ask you to follow a plan. This one expects you to own the timeline—and fix it when reality breaks it.

2 Hour Learning is scaling a national network of microschools designed to deliver a full day of learning in just two hours using AI. That model depends on speed and precision in the real world. Every delay in permitting, every sequencing mistake on-site, every missed handoff slows expansion. This role exists to eliminate those failures and turn construction into a predictable, repeatable system.

You will be on the ground making builds happen. Coordinating contractors. Enforcing schedules. Solving sequencing issues before they become delays. At the same time, you will use AI and digital tools to reduce manual work, improve visibility, and accelerate execution. This is not passive project management. You are the person who steps in when timelines slip and brings them back under control.

If you’ve been close to construction but frustrated by poor coordination, weak accountability, or constant fire drills, this is your chance to take control and do it right—at scale.

What You Will Be Doing

• Coordinate on-site construction activities, working directly with contractors to ensure work is executed in the right sequence and on schedule
• Own and enforce project timelines, tracking milestones, identifying risks early, and driving corrective action when delays occur
• Use tools like Procore, Asana, or MS Project to manage tasks, documentation, and progress across active builds
• Support permitting workflows by tracking submissions, responding to comments, and coordinating with stakeholders to move approvals forward
• Apply AI tools to accelerate planning, documentation, and decision-making, reducing manual effort and improving execution speed

What You Won’t Be Doing

• Accepting a passive role behind a dashboard, tracking updates without intervening when timelines slip
• Managing projects only at a high level without understanding on-site realities and sequencing constraints
• Relying on outdated, manual processes to track progress or communicate with teams
• Avoiding difficult conversations with contractors or stakeholders when deadlines are at risk
• Waiting for perfect information before taking action to resolve issues

Construction Project Lead Key Responsibilities

Drive the on-time execution of school construction projects by actively managing on-site coordination, enforcing schedules, and improving speed and predictability through tools and AI.

Basic Requirements

• Direct experience executing U.S. construction projects, including on-site coordination, contractor management, or schedule enforcement
• Experience owning a project timeline, tracking milestones, enforcing deadlines, and recovering from delays
• Proficiency with a digital project-management tool such as Procore, Asana, or MS Project, including disciplined task and document tracking
• Experience making construction trade‑sequencing decisions that affected the project schedule
• Direct involvement in U.S. permitting workflows, including applications, reviews, revisions, and interactions with authorities having jurisdiction
• Demonstrated use of AI tools to accelerate planning, analysis, documentation, or another real work task, with validation of the output
• Strong problem-solving in ambiguous construction situations and the ability to build productive relationships with contractors, vendors, and external stakeholders
• Openness to direct feedback and rapid iteration
• Willingness and ability to work on-site at least three days per week and travel approximately 60% across the United States based on project needs
• Located in the United States and authorized to work without visa sponsorship

Nice-to-have Requirements

• Experience working across multiple concurrent construction projects
• Exposure to fast-paced or high-growth build environments where timelines are aggressively compressed
• Interest in improving construction processes through automation or systemization

About 2 Hour Learning

Education is broken, but 2 Hour Learning is proving it doesn’t have to be. They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.

With students consistently ranking in the top 1-2% nationally and the top 20% achieving an astonishing 6.5x growth, they’re proving that smarter learning is possible. At 2 Hour Learning, it’s talent and performance that matter.

The company offers a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can be a part of fixing a broken school system.

2 Hour Learning is reprogramming learning for the AI era.

Here’s How They’re Fixing It.

They offer a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can be a part of fixing a broken school system.

Working with us

This is a full-time, W2 employee position with immediate access to benefits (https://support.crossover.com/article/7581-w2-benefits-u-s-paychex-paid-only). All roles are year‑long positions. The compensation level for this role is $100,000 USD/year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5787-US-Chicago-ConstructionPr1