Demo

Crew Supervisor

Cara Chicago
Chicago, IL Full Time
POSTED ON 3/11/2025
AVAILABLE BEFORE 6/11/2025

CREW SUPERVISOR

About Cara Collective

Cara Collective seeks to fuel a courageous national movement to eradicate relational and financial poverty. Our Mission is

to build an inclusive economy by developing employment pathways to advance transformative individual and community success. Through our entities – Cara, Cleanslate, and Cara Plus – we engage job seekers, employers, and other organizations across the country to break the cycle of poverty through the power and purpose of employment.

We believe that there is an incredible and untapped talent pool in our country, one comprised of people often experiencing homelessness and poverty. Our job is to unlock the strengths they already have and showcase them anew to the world. Today, we take the insights gained over the past 30 years to equip other organizations and employers with practices to help build a more inclusive economy.

To ensure that we are centering our work around the individuals and communities we serve, Cara Collective commits to taking an inclusive and equitably approach in all we do : in our program design, diverse representation in our staff, partnerships we choose to enter, and our external and internal communications and policies. We leverage our individuality and differences as a way of deepening community and expanding opportunity in and around our organization.

Discover the impact we are making and explore the impressive numbers behind our success by clicking here :   www.caracollective.org .

About Cleanslate

As a social enterprise undertaken by Cara Collective. Cleanslate is a small but mighty cleaning machine, differentiated by its fast and friendly service and its deep commitment to the community. We provide what some might consider an ordinary service (litter abatement, landscaping, snow removal & power washing) in an extraordinary way, so that all Chicago neighborhoods – from Uptown to South Shore to many communities in between – can take pride in the safety, revitalization, and vibrancy that is created through clean streetscapes serviced by motivated and motivating people. We don’t just get the job done, we do it in a way that makes you feel good too. This unique DNA is what truly sets it apart.

About the Role

The Crew Supervisor will oversee crews performing litter abatement, landscaping, snow removal, and power washing, ensuring that all work is completed to the highest standard. In addition to maintaining quality and efficiency in field operations, this role is responsible for training, mentoring, and evaluating transitional workers as they develop valuable job skills.

As a key leader in Cleanslate’s field operations, the Crew Supervisor plays a crucial role in maintaining the organization’s reputation for excellence. This position requires strong attention to detail and a commitment to quality control, ensuring that Cleanslate continues to deliver exceptional service while empowering workers on their path to long-term employment.

Qualifications

We are excited to offer this opportunity for a mission-driven professional to join our team as Crew Supervisor at Cleanslate. This role is ideal for a hands-on leader who is passionate about fostering strong teams, ensuring high-quality service delivery, and creating pathways to employment for individuals seeking a fresh start.

The Crew Supervisor will play a critical role in overseeing daily field operations, mentoring crew members, and maintaining Cleanslate’s commitment to excellence in exterior maintenance services. This is an incredible opportunity for an individual who thrives in a fast-paced, mission-driven environment and is eager to make a tangible impact on Chicago’s neighborhoods.

Requirements :

  • Experience in the leadership of teams, with strong coaching skills
  • Strong and innovative customer service skills
  • Excellent work ethic and drive to succeed, with ability to excel in a fast-paced and high-pressure environment.
  • Ability to solve practical problems and deal with a variety of unexpected obstacles independently.
  • Must be able to lift heavy objects up to 50 lbs., repeatedly throughout a shift.
  • Capable of working in all weather conditions.
  • Basic understanding of commonly used equipment
  • Must be flexible with schedule and able to work weekends.
  • Must have a valid driver’s license.
  • Comfortable driving 1 / 2 ton crew cab pickup truck

The Responsibilities of the Crew Supervisor :

Operations (70%)

  • Provide overall supervision of Cleanslate’ s exterior maintenance service lines. (including power washing, graffiti removal, snow operation, landscape services, streetscape installation / maintenance, and special events)
  • Provide high attention to quality outcomes when managing projects in the field.
  • Provide hands approach when needed for various landscaping, pressure washing and snow plowing duties.
  • Build and nurture relationships with customers and constituents.
  • Ensure vehicle and equipment is well maintained and cleaned at all times.
  • Ensure all safety protocols are being followed.
  • Perform additional duties as deemed necessary and appropriate by Cleanslate Management.
  • Administrative (10%)

  • Assist with administrative tasks including schedules, evaluations, and reports.
  • Ensure administrative responsibilities are completed accurately and on time.
  • Assist in developing accurate bids for products and services along with Cleanslate’s contract staff.
  • Ensure all photos and / or written documentation is complete, accurate, and delivered on time.
  • Maintenance (10%)

  • Support with equipment maintenance.
  • Work with Field Mechanic on various building projects and machinery repairs as requested.
  • Supervision and team leadership (10%)

  • Provide consistent and strong management presence to ensure a high level of quality control with assigned crew.
  • Evaluate, mentor, supervise, coach, and support transitional workers as part of their learning experience.
  • Input crew performance evaluations into database on a daily basis
  • Oversee transitional worker customer service interactions.
  • Reports To

    Account Manager

    Direct Report(s)

    The Crew Supervisor provides supervision and mentorship to the Field Service Representatives on route.

    Team Culture

    Cara Collective has a strong team culture that values collaboration, communication, and camaraderie. We consistently measure staff satisfaction through employee surveys and have found that year over year, the vast majority of staff agree that Cara Collective is a great place to work and grow. This high level of employee satisfaction reflects our dedication to creating a positive and fulfilling workplace for all members of our team.

    Starting Pay Range

    We take budget and starting salary very seriously. We market our roles and use a salary analysis tool called Payscale and offer competitive, market-based compensation to all employees.

    This position offers an expected starting pay of $20.00 per hour.

    The position is temporarily funded , by a grant which is set to expire on November 30, 2025.  We expect this position to end when the funded grant period ends.

    Benefits

    Our comprehensive benefit package include :

  • Medical, Dental, Vision Plans
  • Basic Life Insurance
  • Long Term Disability
  • Personal Technology Reimbursement
  • 4 Weeks Paid Parental Leave
  • Starting with 17 Vacation Days, 8 Sick Days,
  • 14 Paid Holidays
  • Employee Paid Benefits

  • Pre-Tax Medical Flexible Spending Account
  • Pre-Tax Dependent Care Account
  • Pre-Tax Transit & Parking Options
  • Supplemental Life and AD&D Insurance
  • Short-Term Disability Insurance
  • 401(k) Retirement Plan (employer match up to 4% upon hire & immediately vested)
  • As of this posting, we annually review our benefit offerings to meet our employees' needs and be competitive in the market. All listed benefits offerings a at the discretion of the employer.

    Equal Opportunity Employer

    Cara Collective and Cleanslate are committed to creating a diverse work environment and is proud to be an equal opportunity employer. Cara Collective does not discriminate on the basis of race, color, national origin, sex, gender identity, religion, sexual orientation, age, disability, parental status, veteran status, or any other protected status under applicable laws. We encourage individuals of all backgrounds to apply. If you are a qualified candidate with a disability, please email us at kboelkens@carachicago.org if you require reasonable accommodation to complete this application.

    Salary : $20

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