Executive Assistant to the CEO

About us

Players Sport & Social Group (PSSG) runs adult recreational leagues and events for more than 80,000 Chicagoans a year. That includes volleyball, soccer, softball, kickball, pickleball, basketball and more, played at beaches, parks and gyms across the city. We also just opened Players Sports Center (PSC), a multi-sport indoor facility. We’re a small team that cares about running great programs and building community through sports.

The role

Running two growing businesses leaves our CEO buried in email and admin. You’ll take that work off his plate so he can spend his time on sales, marketing, programming, landing contracts and strategy.

This is more than calendar management. You’ll be the CEO’s right hand and the person who makes sure things actually get done. When he makes a decision, you turn it into a task with an owner and a deadline, and you follow up until it’s finished. If you love order, clear communication and closing loops, you’ll do well here.

What you’ll do

Inbox, calendar and priorities

• Triage the CEO’s inbox every day. Flag what needs him, draft replies to the rest and keep threads moving.
• Manage his calendar. That means scheduling meetings, protecting focus time, preparing agendas and making sure he goes into every meeting with what he needs.
• Keep one current master to-do list and review it with him every week.

Delegation and accountability

• Turn the CEO’s decisions into clear assignments, each with an owner, a deadline and a definition of done.
• Track every delegated item and follow up with staff politely and persistently until it’s complete.
• Raise blockers and slipping deadlines early, before they turn into problems.

Systems and records

• Build and maintain SOPs, templates and checklists for recurring work.
• Organize contracts, renewals, vendor agreements and key files, with PSSG and PSC records kept clearly separate.
• Track important dates like contract renewals, permits, insurance and venue agreements so nothing lapses.

Communication

• Speak for the CEO with partners, venues, vendors, sponsors and staff, in writing and by phone.
• Draft emails, announcements and documents in his voice.

Projects and events

• Help carry company initiatives from kickoff to finish: plan timelines, coordinate the people involved and track progress.
• On in-person days, support operations at Players Sports Center and at larger PSSG events.

Operating rhythm

You’ll own the checklists and dashboards that keep the company on track toward its goals.

• Weekly: Inbox and task review, delegated-item tracker, calendar prep, a snapshot of key numbers, and a weekly brief for the CEO
• Monthly: Goal dashboard for PSSG and PSC, review of leadership action items, and a check of contract and renewal dates
• Quarterly: Scorecard for goals and initiatives, prep for planning sessions, and an audit of records and compliance

What success looks like

• First 30 days: You know the business, the team and the CEO’s priorities. You run the inbox and calendar, and the master to-do list and delegation tracker are up and running.
• First 60 days: The weekly rhythm runs without reminders. The CEO gets a clear weekly brief, and delegated work is tracked and followed up on consistently.
• First 90 days: The monthly dashboards and contract tracking are in place, core SOPs are written, and the CEO has measurably more time for sales and strategy.

You’re a fit if you

• Are highly organized and close every loop
• Write clearly and professionally, including in someone else’s voice
• Can hold people accountable while staying polite and persistent
• Work independently and reliably while remote, with little day-to-day supervision
• Handle confidential information with discretion
• Are comfortable with Google Workspace (Gmail, Calendar, Drive, Docs) and spreadsheets
• Can be at your desk early (6 or 7am) and respond reliably during those hours

Nice to have

• Experience as an executive assistant, chief of staff or in operations
• Experience with HubSpot, Asana or similar CRM and project management tools
• Familiarity with recreational sports, events or facility operations
• Experience building SOPs, dashboards or reporting systems

Logistics

• You’ll need a reliable computer and internet connection for remote work
• You’ll need to get to Players Sports Center and other Chicago event locations 1–3 days a month

We are an equal opportunity employer and …