Business Operations & Contractor Manager

City Wide Chicago Shores is searching for a driven, hands-on Business Operations & Contractor Manager to be the connective tissue within our team. In this pivotal role, you’ll own both day-to-day business operations and the pipeline of independent contractors (ICs) who deliver outstanding service for our clients.

This isn’t an “oversee from a distance” manager gig. We need an energetic, collaborative, respected team member who thrives on daily action: researching, calling, qualifying, interviewing, recruiting, onboarding, and supporting independent contractors every single day; while also keeping office functions and business processes running smoothly, with organization and integrity.

If you pride yourself on “getting things done,” building strong professional relationships, and want to help shape our culture while growing your career, we want to meet you.

What you will do...

• Independent Contractors Recruitment & Onboarding:
  Research, source, reach out, call, screen, interview, and onboard a steady pipeline and bench of highly qualified independent contractors (ICs); keep active records and continuously build relationships to ensure we always have coverage.
• Contractor Management:
  Set expectations, collect compliance/insurance documents, track ongoing requirements, and ensure all ICs meet City Wide’s operational and quality standards.
• Office & Business Operations:
  Oversee office administration, help maintain CRM data, manage supplies, and keep reporting, proposals, contracts, and compliance documents up-to-date and audit-ready.
• Performance Tracking & Reporting:
  Maintain meticulous dashboards and records to ensure leadership always has visibility into operational and contractor status; proactively communicate risks and needs.
• Team Communication & Culture:
  Collaborate with Sales, Operations, and Leadership; support team engagement, recognition, and training events for contractors and staff alike.
• Be the Face of City Wide:
  Represent our brand professionally and confidently in all interactions with contractors, clients, and partners - building mutual respect and loyalty by leading through action.
• Other Duties as Needed:
  Support President/Owner and other teams as business needs evolve.

Requirements

• 5+ years of business operations, executive support, recruiting, office administration, or contractor management experience (facility solutions or service industry experience a plus). Strong at following proven systems and adapting them to real-world needs.
• Ability to recruit, qualify, and onboard a high volume of independent contractors of varied specialties.
• Proven “lead by example” approach: you excel on the phone, in interviews, and in the details; no task too small if it helps the team win.
• Confident clear communicator (i.e. strong writing, speaking, and presentation skills), who builds trust and culture, leads onboarding, and partners closely with management. Confident, tactful, and able to perform well under pressure
• Bilingual English/Spanish a plus
• Confident using MS Office Suite (Excel, PowerPoint, Word) and MS Dynamic CRM platforms
• Positive, professional demeanor with a sense of urgency and high personal standards
• Relationship builder - able to command respect while staying approachable and solution-oriented.
• Comfortable working onsite and supporting multiple functions in an office environment
• Reliable transportation and willingness to be on-site daily.

• Highly organized, detail-oriented, and structured in approach
• Strong moral compass, community-minded, and a collaborative team player
• Competitive leadership background (i.e. participation in team sports, team captain, or similar roles)
• Full ownership mentality of business operations "it won't fail because of me" mentality

Success Measurement

• Independent Contractor (IC) Talent Available & Pipeline Health: Maintain a continuously growing and high-quality pipeline of ICs across core service categories. Develop and maintain an efficient, repeatable recruiting process that aligns with our cost structure and service standards
• SOPs, Scorecards & Performance Dashboards: Build and maintain up-to-date operating documents and tracking tools that support decision-making and accountability
• Internal Culture & Communications Effectiveness: Strengthen team alignment, communication, and culture of perform