Community Stewards Lead

Chicago Sun-Times

. Oversee the initial cohort of Community Stewards and build the systems, training, coaching, and support infrastructure for the stewardship model .

Posted 10/9/2026full-timeChicago • Illinois • United StatesSenior💰 $69,000 - $86,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in community management, coaching, and program development, with a strong focus on building scalable systems and facilitating effective training. Proven ability to assess community health and performance while adapting strategies to meet diverse neighborhood needs.

Highest-signal resume keywords

Community ManagementCoaching And DevelopmentTraining FacilitationProgram DevelopmentCross-Functional Collaboration

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills

Performance AssessmentPlaybook DevelopmentWorkflow DesignQuantitative AnalysisQualitative Analysis

Soft Skills

MotivationJudgmentAdaptabilityFacilitation

Tools & Technologies

DashboardsReporting Tools

Industry Keywords

Community ProgramsNeighborhood EngagementCivic EcosystemChicago NeighborhoodsAmbassador Networks

About the role

Key responsibilities & impact

Oversee the initial cohort of Community Stewards and build the systems, training, coaching, and support infrastructure for the stewardship model
Manage, coach, and motivate stewards serving five neighborhood communities
Lead interviews, selection, onboarding, ongoing management, performance conversations, and offboarding as needed
Establish performance expectations, responsibilities, deliverables, and support plans
Build and maintain a stewardship playbook covering onboarding, community building, content, moderation, events, growth, editorial standards, and platform use
Create onboarding and posting guides, FAQs, content calendar templates, event checklists, platform guidance, and other steward resources
Design and facilitate workshops, training sessions, peer learning, and asynchronous peer support
Organize in-person cohort opportunities, including early site visits and periodic visits throughout the year
Coach stewards on neighborhood strategy, resident engagement, community culture, content, moderation, civic connections, and trusted local information
Track community health and steward performance against growth, retention, and engagement measures
Establish dashboards and reporting tools; compile regular community and program performance assessments
Serve as the primary connection point between Community Stewards and the Chicago.com team
Partner with product, marketing, editorial, and external product teams to surface feedback and improve tools and workflows
Document lessons and prepare the stewardship model for potential expansion into additional Chicago neighborhoods
Recruit and onboard additional stewards and adapt training if expansion proceeds

Requirements

What you’ll need

Experience managing, coaching, or developing people, particularly individuals working independently or across multiple locations or communities
Experience building or operating community programs, membership programs, ambassador networks, field organizations, or similar distributed models
Strong facilitation and training skills
Experience developing playbooks, documentation, training programs, workflows, or other systems that make an emerging program more consistent and scalable
Strong understanding of online community management, including moderation, community standards, engagement, disagreement, and misinformation
Experience using quantitative and qualitative information to assess performance, identify problems, and adjust strategy
Ability to coach individuals toward clear goals while adapting support to different neighborhoods, personalities, and community contexts
Strong cross-functional collaboration skills with product, marketing, editorial, and external partners
Comfort working in an early-stage environment where processes, tools, and responsibilities will continue to evolve
Strong judgment when navigating sensitive community issues or balancing program consistency with individual neighborhood needs
Familiarity with Chicago's neighborhoods, civic ecosystem, and community organizations is strongly preferred

Benefits

Comp & perks

Medical insurance
Dental insurance
Vision insurance
Vacation
Holidays
Life insurance
Disability coverage
Retirement savings
Commuter benefits plan
Broad and generous benefits package for employees at hire and in the years to come