Business Operations & Contractor Manager

Overview

Business Operations & Contractor Manager — City Wide Chicago Shores is seeking a driven, hands-on leader to be the connective tissue within our team. This role owns day-to-day business operations and the pipeline of independent contractors (ICs) who deliver outstanding service for our clients.

This is not a distant management role. We seek an energetic, collaborative team member who thrives on daily action: researching, calling, qualifying, interviewing, recruiting, onboarding, and supporting independent contractors, 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.

• Independent Contractors Recruitment & Onboarding:
  Research, source, reach out, call, screen, interview, and onboard a steady pipeline of highly qualified ICs; maintain active records and build relationships to ensure coverage
• Contractor Management:
  Set expectations, collect compliance/insurance documents, track ongoing requirements, and ensure ICs meet City Wide's operational and quality standards
• Office & Business Operations:
  Oversee office administration, maintain CRM data, manage supplies, and keep reports, proposals, contracts, and compliance documents up-to-date and audit-ready
• Performance Tracking & Reporting:
  Maintain dashboards and records to provide leadership visibility into operations 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
• Face of City Wide:
  Represent the brand professionally in interactions with contractors, clients, and partners
• Other Duties as Needed:
  Support President/Owner and other teams as business needs evolve

• 5+ years of experience in business operations, executive support, recruiting, office administration, or contractor management (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 ICs with varied specialties
• Proven leadership by example: strong on the phone, in interviews, and in the details; no task too small if it helps the team win
• Confident communicator (writing, speaking, and presenting) who builds trust and culture; able to perform under pressure
• Bilingual English/Spanish a plus
• Proficient with MS Office Suite (Excel, PowerPoint, Word) and MS Dynamics CRM
• Positive, professional demeanor with a sense of urgency and high personal standards
• Relationship builder who commands 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 (e.g., participation in team sports, team captain, or similar roles)
• Full ownership mentality of business operations

• Independent Contractor talent availability & pipeline health: maintain a growing pipeline of ICs across core service categories and develop a repeatable recruiting process
• SOPs, scorecards & performance dashboards: keep operating documents and tracking tools up to date
• Internal culture & communications effectiveness: strengthen team alignment and culture of performance
• Owner & partner enablement: act as a force-multiplier for the owner/operator and a reliable hub for stakeholders

• Want to grow fast and gain visibility, responsibility, and influence early
• Know how to get things done using proven approaches
• Are resourceful and leverage City Wide’s content library and support network
• Take pride in outcomes and do things right
• Have a problem-solving mindset: research, ask questions, and move forward
• Thrive in ownership and require minimal micromanagement
• Bring…