Work Crew Site Supervisor

Please see details about this job opening below. To apply, click here for the job application.

The Opportunity

We’re looking for Work Crew Site Supervisors (known internally as Site Supervisors) to help us live our mission to prepare people with recent criminal convictions for securing employment. Work Crew Site Supervisors support, supervise, and train work crews of 6-8 participants. Site Supervisors create uplifting work environments for our participants that ensure their safety, provide on-the-job coaching, encourage and empower team members to seize each opportunity for building knowledge and skills and foster engagement and accountability across the crew. Through this work, Work Crew Site Supervisors make a real impact on our participants’ lives.

Why this work is important….

Every participant works as part of a transitional work crew to gain hands-on experience and income while concurrently working with CEO’s vocational staff to identify and secure long-term employment -- transitional work opportunities contribute to greater stability as an individual is getting back on their feet.

Who You Are

  • You have a proven track record of leading teams to achieve success, and your efficient and friendly customer service makes you a trusted partner.
  • You exercise compassion toward the team you’re leading but balance this with a straightforward approach that ensures you meet the needs of your customers. You are excited to learn evidence-based communication techniques such as Motivational Interviewing in order to more effectively work with team members.
  • You are respectful, fair, and patient.
  • You pride yourself in your ability to communicate effectively with individuals of varying backgrounds and experiences. You recognize the value of continuous communication, looping others into project status and any challenges that arise.
  • You have strong organizational skills and are able to delegate, prioritize, and manage you and your team’s time effectively to meet project deadlines.
  • You foster a strong team spirit and enjoy providing 1:1 support to team members who may need a little extra support.
  • You are deeply passionate about and committed to excellence and having an impact on our participants’ lives.

Additional Responsibilities

Key responsibilities of the Work Crew Site Supervisor include but are not limited to:

  • Ensuring customers’ work orders are completed to a high standard on a daily basis
  • Establishing and maintaining positive staff morale through modeling sound leadership and teamwork
  • Assigning job duties to crew members and setting reasonable goals for completion
  • Monitoring crew members on job performance and productivity, providing appropriate feedback and/or additional training as needed
  • Maintaining a line of sight of all participants
  • Maintaining a safe, secure, and healthy work environment by following and enforcing standards and procedures and complying with legal regulations and by reporting any matters that threaten the smooth operation of the training crew to your supervisor
  • Completing any necessary daily reporting tasks

The Nitty Gritty Qualifications

  • You must be able to work a typical schedule of a four day work week from 6:00AM-3:00PM, and be willing to work outdoors in all weather. Additional hours including evening and weekend shifts may be assigned on an as-needed basis.
  • High school diploma, along with at least one year of supervisory experience; experience within a vocational trade (construction, landscaping, building maintenance, grounds maintenance, land surveying) preferred
  • Valid driver’s license with a good driving record
  • Previous safety training preferable, though training will be provided to the hired candidate
  • Must be able to: Consistently lift and move objects up to 75 pounds; stand, kneel, bend, and climb in order to complete projects; work outdoors; walk or stand for long periods of time; drive a 12 passenger van with an attached trailer; operate a smartphone


Please note there is a 90-Day probationary period for Site Supervisor new hires in San Diego. After the first 90 days and pending review of the Site Supervisor’s performance, Site Supervisors can be brought on as regular full-time employees. If brought on as a regular full-time employee, annualized compensation falls between $35,000-37,000 as overtime is frequently incurred. Full time Site Supervisors can also access CEO’s comprehensive benefits package, which includes medical and dental coverage, paid parental leave, participation in a retirement plan, sick and vacation leave, paid holidays and more.

More About Us

We welcome diversity and highly encourage applications from people of color and people with convictions. We are an equal employment opportunity for all regardless of race, color, citizenship, religion, national origin, sex, sexual orientation, gender identity or expression, age, disability, veteran or reservist status, or any other category protected by federal, state, or local law. Learn more at

Please click here for the job application.