Windy City Harvest Community Outreach and Field Supervisor

Title: Community Outreach and Field Supervisor (Chicago, IL)

Exemption Status: Non-Exempt 

Department: Windy City Harvest 

Reports to: Manager of Workforce Development

Year-Round, Full Time

Supervises: 5 to 10 farm production crew members 

Year-Round Full-time employees of the Chicago Botanic Garden are eligible for the following Benefits:

• 2026 A Guide to Your Benefits JP.pdf

Compensation Philosophy:

At the Chicago Botanic Garden, our compensation philosophy is rooted in our core values: Growth, Understanding, Resilience, and Trust through Transparency. We are committed to creating a workplace where everyone feels respected, valued, and appreciated.

The starting salary for new staff members is determined by considering the salary range assigned to the position and by reviewing the candidate’s qualifications for the job as compared with job responsibilities. Prior work experience should be considered in determining the salary offer, provided that it is relevant to the job. Additional factors such as secondary language proficiency or advanced degrees that enhance performance may also be considered. A candidate’s salary may exceed the minimum amount based on factors such as experience, additional skills (e.g., secondary language proficiency), or pertinent degrees that enhance the individual’s contribution to the role but are not required. Opportunities for increased compensation are provided through referral bonuses, shift differentials, Thank You Pay, promotions, and periodic pay increases based on the Garden's overall performance and financial budgets.

Our total compensation and benefits package is people centric. We prioritize employee wellness across three pillars: physical, mental, and financial. Our goal is to offer innovative total rewards that support continuous professional growth, personal development, and provide the flexibility needed to balance personal and professional commitments.

Position Overview:  

The Chicago Botanic Garden’s Windy City Harvest is looking for a dedicated Community Outreach and Field Supervisor to work with our transitional jobs and workforce development program. The Community Outreach and Field Supervisor will be part of a collaborative team environment working closely with all members of our Windy City Harvest program and operations team. 

The Windy City Harvest Corps program employs 30 to 40 justice-involved individuals and veterans for two 14-week cohorts each year in closely mentored, full-time, paid transitional jobs. Our goal is to support our graduates in finding full-time, long-term employment.   

The Community Outreach and Field Supervisor will lead participant recruitment and community outreach, maintain a structured presence across program crews to build relationships and support participant awareness, connect participants to community resources at key program moments, and lead alumni engagement and follow-up after graduation. This role also serves as backup field supervision coverage as needed. 

The ideal candidate has experience with community outreach and workforce development, is comfortable building relationships across community organizations and reentry partners, and communicates proactively and transparently with program staff. Lived or professional experience with the justice system is preferred. 

For more information on the Corps program, please visit:     

chicagobotanic.org/urbanagriculture/programs/corps

Responsibilities

In this role you will be responsible for the following: 

Recruitment & Community Outreach

• Lead participant recruitment for two annual cohorts of 30 to 40 participants each, including outreach to reentry partners, social service agencies, and community organizations 
• Coordinate and facilitate information sessions; track interest and support conversion of attendees into completed applicants
• Represent Harvest Corps at partner site visits, outreach events, and community tables
• Maintain and grow the partner referral network; provide regular feedback to partners on referral quality and program fit
• Support participant hiring and onboarding logistics in collaboration with Workforce Development Manager 
• Track recruitment metrics and provide regular updates to the Workforce Development Manager

Structured Crew Presence & Participant Support 

• Build consistent relationships across all crews, maintaining awareness of participant progress and challenges
• Serve as resource and referral connection point at key moments, including intake, onboarding, IEP conversations, and job placement
• Connect participants to community resources including housing, legal aid, childcare, mental health services, and transportation through warm referrals to external partners
• Surface participant concerns and emerging issues to the Workforce Development Manager in a timely and transparent manner
• Co-facilitate Friday job club activities, workshops, and employability programming as assigned
• Reinforce program standards and culture of accountability and mutual respect
• Serve as backup field supervisor when gaps require coverage 

Alumni Engagement & Follow-up

• Conduct 30, 90, and 180-day follow-up outreach with program graduates to track employment outcomes, and monitor well-being and employment stability
• Maintain accurate alumni contact records and contribute employment verification data to grant compliance reporting 
• Connect alumni experiencing challenges back to resources and support
• Support development of alumni engagement overt time in partnership with the Workforce Development Manager 

Farm Operations

• Provide hands-on guidance and work alongside Corps participants, production assistants, and apprentices to complete farm-site tasks and meet production goals including planting, weeding, harvesting, post-harvest handling, composting, and site maintenance 
• Demonstrate best practices in market gardening and train participants in diversified vegetable production 
• Follow established crop plans, task lists, and production schedules 
• Give weekly safety talks; complete required production and safety logs to meet food and safety standards  

 Qualifications  
Our ideal candidate will have the following:  

• Lived experience with the justice system or direct professional experience supporting justice-involved individuals is strongly preferred
• Available to work Monday through Friday, 8 a.m. to 4 p.m., with flexibility for site assignments, weather-related schedule changes, and operational needs 
• One year of experience gardening, farming, landscaping, working outdoors, or in the local food system    
• Background in workforce development, job readiness programming, or adult education
• Experience making warm referrals or navigating social service systems with participants or clients
• Understanding of and commitment to the model of transitional jobs    
• Demonstrated experience in leading others, enforcing workplace standards, and providing constructive verbal and written feedback 
• Strong relationship-building skills with team members, program participants, and employment partners   
• A valid driver’s license with a clean driving record    
• Commitment to being a supportive resource for program participants, community residents, and project partners     
• Excellent communication skills: email, phone, and in person
• Willing to work with all departments and/or at all farm sites depending on the operational needs

Physical Demands:  

This is an urban farm setting. Staff must be able to work on their feet all day in all weather conditions performing manual labor. This will involve frequent lifting, standing, walking, bending, farm tool usage, machinery operation, and speaking to public, staff, and program participants. Staff is also required to lift, push, and pull items up to 50 pounds. Staff is expected to work in multiple locations.   

Why Apply? 
 Come work in a setting that is like no other as you support our mission: We cultivate the power of plants to sustain and enrich life. Take the first step toward being one of the employees who make the Garden one of the treasures of the Forest Preserves of Cook County. Apply today. Please note that applicants who do not meet the required qualifications will not be considered.

We are an Equal Opportunity Employer and do not discriminate against any employee or applicant for employment because of race, color, sex, age, national origin, religion, sexual orientation, gender identity, status as a veteran, or basis of disability, or any other federal, state, or local protected class.

Disclaimer: The above statements are intended to describe the general nature and level of work being performed by people assigned to this classification. They are not intended to be an exhaustive list of all responsibilities and qualifications required of personnel so classified.

In accordance with Title IX of the Education Amendments Act of 1972, the Chicago Botanic Garden does not discriminate on the basis of sex in its programs or activities, including in employment or admissions. Please call (847) 835-8264 to contact our Title IX coordinator should you have questions or concerns. Please do not call this number to inquire about job postings or the status of your application, or with solicitations from companies or third-party recruiters.