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 performance
Owner & Partner Enablement: Act as a true force-multiplier for the owner/operator and a reliable hub for internal and external stakeholders
You Will Thrive Here If You:
Want to grow fast; you'll gain real visibility, responsibility, and influence early
Know how to get things done; not by starting from zero, but by using what's already working
Are resourceful; you'll use City Wide's massive content library and our support network to fuel execution
Take pride in outcomes; from every email you send to every contractor you recruit, you'll care about doing it right
Have a "figure it out" mindset; when something isn't clear, you research it, ask questions, and move forward
Thrive in ownership; you don't need micromanagement to do your best work
Bring strong business tech skills; you're confident in Excel, PowerPoint, Word, and CRMs
Communicate like a pro; you write, present, and engage clearly and persuasively
What This Role Can Become:
If you perform and deliver, this role can evolve into far more. As we grow our client base and team, your influence will grow with it.
We give you ownership of outcomes with proven tools for success. You'll have direct access to decision-making and the support system of an entire network.
The hard work of figuring out "what works" has been done. Your job is taking what works and making it work exceptionally well for our territory. With the right person supporting our President, and executing proven systems, this territory will become one of the top performers in the City Wide network.
Benefits
City Wide Chicago Shores, we believe in flexible and personalized healthcare benefits. That's why we offer tax-free reimbursements for your medical premiums and expenses, plus access to dental and vision plans from top carriers. You choose what works best for you and your family.
A monthly QSEHRA health reimbursement to support your medical premiums and qualified healthcare expenses
Access to dental and vision coverage through nationally recognized carriers, with the option to enroll at competitive group rates
A company-sponsored 401(k) plan with matching, paid time off, Community enrichment, EOE...
WHY THIS ROLE IS RECESSION-RESILIENT & FUTURE-PROOF
This role is recession-resilient because it supports the essential services that businesses rely on to stay clean, safe, and operational; regardless of economic conditions. It's future-proof because you'll be mastering systems, tools, and leadership skills tied directly to growth, scale, and long-term operational excellence. You'll enjoy reliable earning potential, continuous professional growth, and the chance to become a leader within a supportive, high-performance team.
VALUES & CULTURE
Bring value, know your customer, own it, celebrate your teammates, and always be professional. Join a team committed to helping you become the best version of yourself, where loyalty, learning, and results are recognized and rewarded.
More on City Wide...
City Wide Facility Solutions is a fast-growing company with over 100+ extremely selective franchise locations across the United States and Canada. Founded in 1961, City Wide Facility Solutions is the largest management company in the building maintenance industry. We have over 60 years in the business and continue to experience high growth and profitability across our franchise businesses. Our culture supports the company's Mission to create a Ripple Effect by positively impacting the people and communities they serve. Read more about City Wide at www.gocitywide.com
City Wide is an Equal Opportunity Employer.
