League Operations Manager

About Us

Chicago Super League is building the first community‑owned soccer pyramid on the South Side. We have 24 clubs, 3 leagues, 100 players, youth and adult divisions, and a mission to destroy pay‑to‑play. We're a fast‑growing organization moving at startup speed.

This role starts part‑time (20 hours/week), but it is designed to grow. The goal is simple: if you build the systems and run the operations well, this role becomes full‑time within 6‑12 months. You are not just filling a position — you are building your own department.

This is not a “keep things running” role — this is a build the foundation role.

Location: Remote‑first. You'll work from home, with on‑site presence for match days, field visits, and key meetings (South Side Chicago).

• Simplify our current tech stack (Airtable, Notion, Google Sheets, Spond, Hubspot, etc.)
• Build a single clean system for player onboarding and database management
• Create a master database (private public‑facing) for all players, teams, and coaches
• Track key player data: roster numbers, jerseys/uniforms, paid status, sponsored players, inactive players, participation history
• Design a simple entry point (form) for new player registration
• Streamline communication channels

• Book refs and fields for all matches (remote coordination with parks and refs)
• Confirm team availability each week (email/text/Whats App/etc)
• Manage match day logistics remotely (equipment checklists, check‑in coordination)
• Ensure compliance with Chicago Park District and city requirements

• Help build match days into exciting events as we scale
• Coordinate photographers, sponsor tables, food vendors, and music (remote planning on‑site coordination)
• Support live streaming and content capture
• Elevate the player and fan experience

• Move fast. Build in small iterations. Don’t wait for perfect.
• Adapt quickly as the league evolves
• Document processes so they can scale

• Organized: You can track 100 players, multiple teams, and weekly logistics without dropping the ball.
• Systems‑minded: You see chaos and build order. You don't just manage — you improve.
• Self‑starter: You don't need someone to tell you what to do next. You see what needs to happen and do it.
• Comfortable with change: This is a startup. Things shift weekly. You adapt and keep moving.
• Good with people: You'll work with players, coaches, refs, parents, and sponsors. You communicate clearly and professionally.
• Soccer‑adjacent (a plus): You don't need to be a coach, but you should understand the game and the culture.
• Remote‑capable: You can work independently, stay on top of communication, and deliver without someone looking over your shoulder.

• 2 years of experience in operations, project management, case management, or a similar role
• Strong proficiency with Google Sheets (or Airtable) and database management
• Excellent written and verbal communication
• Ability to work independently and remotely
• Comfortable with technology and learning new tools quickly
• Chicago‑based preferred (for on‑site)
• Bilingual Spanish is a strong plus
• Love Soccer
• DCFS clearance or willingness to obtain is a plus

• Start: $2,500/month (part‑time, 20 hours/week, 1099 contractor)
• Goal: Full‑time role within 6‑12 months, with increased compensation and benefits

You are not just running logistics. You are building the foundation for the first community‑owned soccer pyramid in Chicago. Every system you build, every match you run, every player you track — it all contributes to something bigger: a league that is accessible, professional, and built for the community.

If you want to build something that matters, this is your role.