Head of Operations

Link to apply listed at the bottom of this Job Description. Only applications submitted through this link will be considered.

WHO WE ARE

Helping Hands Cleaning Services is a leading cleaning company serving residential and commercial clients across the Chicagoland Area. We have built our reputation on quality, reliability, and a team that takes real pride in the work they do inside our clients' homes and offices. We are now entering an exciting chapter of growth as we scale both divisions and build the operational foundation for a franchise-ready future.

Our mission is to impress CUSTOMERS with outstanding service and provide them with free time and peace of mind while taking care of EMPLOYEES in an environment in which they love to work and are encouraged towards opportunities of growth.


Our Core Values:

• Honesty: We demonstrate integrity at all times and hold ourselves to the highest standards of accountability.
• Communication: We are committed to providing transparent information to our internal and external clients.
• Respect: We strive to act positively and professionally as we serve people of all backgrounds.
• Hard work: We seek to deliver excellence in our service by working hard to exceed your expectations.
• Reliability: We are dedicated to delivering consistent and dependable service, ensuring that we always meet and exceed client expectations.

We are looking for someone who genuinely connects with our mission and values. This alignment is essential for success in this role.

JOB DESCRIPTION

The Helping Hands Cleaning Service team is seeking a results-driven, hands-on Head of Operations with a proven track record of bringing structure and scale to growing, multi-division service businesses. This is a high-level leadership role for an operator who can build a documented, system-led, scalable organization, and who is equally comfortable designing the strategy and rolling up their sleeves to execute it.

The Head of Operations owns the day-to-day management of the business so the founder can focus on high-level vision and product. The application code word is EMPOWER. You will design and install the systems, SOPs, KPIs, and communication rhythms that align strategy with execution, giving leadership clarity and transparency over performance while enabling the company to keep growing at speed.

WHAT MAKES THIS ROLE UNIQUE

You will step into a company with strong momentum and a clear growth ambition, and your job is to build the operational backbone that turns that ambition into a repeatable, scalable machine. You will be the steady, tactical partner to a high-drive founder, taking ownership of the management layer so the business runs smoothly without requiring the founder in every detail.

This role spans two divisions and a diverse, bilingual workforce that includes office teams, field supervisors, and technicians working on-site in homes and offices. You will bring these groups into one cohesive ecosystem, build genuine accountability at the supervisory level, and create communication that flows clearly in both directions, from leadership vision down to the field, and from the field back up to the office.

This is a full-time, on-site W2 position based in Elmhurst, Illinois. Given the critical nature of this role, we host a rigorous, 4-part application process to ensure the right fit.

RESPONSIBILITIES (TASKS ASSOCIATED WITH THE ROLE):

Operational Leadership & the Management Hat

• Serve as the primary manager for the leadership layer across Sales, Marketing, Operations, and Customer Success, freeing the founder to focus on strategic vision and product
• Lead the company through evolving team structure and systems to meet the highest standards of client experience
• Coach and develop emerging leaders across both divisions into confident, accountable operators

Systems, SOPs & Single Source of Truth

• Review existing SOPs, identify gaps, and codify tribal knowledge into clear, accessible Standard Operating Procedures for each division
• Integrate a fragmented set of tools and platforms into one centralized, trackable single source of truth for projects, tasks, and information
• Redesign and optimize company systems to maximize service quality, efficiency, and scalability

KPIs, Dashboards & Accountability

• Build KPIs and leading indicators for each department and individual, moving beyond lagging revenue targets alone
• Install accountability at the supervisory level so leaders can confidently hold their teams to clear standards and daily metrics
• Create clear, relevant dashboards that give the founder and leadership visibility into performance without requiring them to dive into the details

Financial Oversight

• Build and oversee financial structure and reporting, including a transparent, automated P&L with founder visibility
• Help formalize and document compensation, bonus, and incentive structures in writing to keep the company aligned with the industry and attractive to new hires

Communication & Meeting Rhythm

• Establish a professional communication rhythm, including All Hands and leadership meetings, to replace heavy reliance on one-to-one meetings with the founder
• Build a meeting structure with clear agendas that drive efficiency, transparency, and decisions
• Translate revenue targets into an authentic, unifying mission that gives the team a shared "why" beyond the numbers

REQUIREMENTS (EXPECTED PROFICIENCIES):

Experience (Non-Negotiable)

• Proven track record as a seasoned operator who has built operational structure and scaled a growing service business, ideally across multiple departments or divisions
• Experience serving as the tactical "steady hand" to a high-drive founder, moving the owner out of daily operations
• Experience overseeing diverse functions simultaneously, including Sales, Customer Success, Administration, Marketing, and field teams, so they function as one cohesive unit rather than silos
• Experience building the infrastructure required to scale from a team of generalists toward a specialized, mid-market organization
• History of building culture and team camaraderie in a diverse, distributed, or bilingual environment
• Demonstrated proficiency in leveraging AI tools as part of daily work, with the ability to effectively navigate platforms such as Claude, Claude for Work (Cowork), and Claude Code to research, analyze, problem solve, and improve operational efficiency.

Core Competencies

• System architecture and automation skills to integrate a disjointed tech stack and eliminate manual processes
• KPI development expertise, with mastery of leading indicators and the ability to cascade and refresh goals as the team grows
• Expert SOP and process documentation skills
• Strong financial acumen, including financial structure creation, P&L oversight, and modeling, to set the business up for transparent, data-based decisions
• Change management skills to bring stability, accountability, and new standards to a team adjusting to a more structured way of working

Critical Soft Skills (Deal-Breakers)

• Radical transparency and the backbone to give a founder honest feedback, including on the impact of their leadership style on the team
• High emotional intelligence to navigate a diverse culture and bridge the gap between field technicians, leadership, and clients
• A balanced managerial lens, strong enough to hold high performers accountable to core values and daily metrics, and empathetic enough to develop people rather than only critique them
• Clarity of purpose, with the ability to translate revenue targets into an authentic mission the whole team can rally behind

Technical & Logistical Requirements

• Conversational Spanish is a plus for this position. (Not a requirement)
• Ability to work on-site in Elmhurst, Illinois, and travel as needed across the Chicagoland service area
• Exceptional attention to detail, time-management, and organizational skills
• Data-driven decision maker who can analyze information and make critical choices based on evidence
• Candid and direct communicator with strong interpersonal, verbal, and written skills in English
• Ability to to perform on site customer visits as needed to execute performance reviews and management practices for supervisors & ops leaders across commercial and residential. We do not see this needing to be daily or weekly, but it is required to effectively evaluate our leadership team.
• Ability to work in office at 675 St Charles Rd, Elmhurst, IL 60126

Mindset & Cultural Fit

• You hold yourself to the highest standards of performance and stay resilient in the face of obstacles
• You thrive in a fast-growing environment and see building structure from the ground up as an opportunity, not a burden
• You are a confident, self-directed leader who can manage up, hold boundaries, and bring calm and clarity to a busy business

WHAT SUCCESS LOOKS LIKE

• First 30 days: Learn the business deeply, build trust with the founder, leadership, and field teams, and map current systems, SOPs, and pain points across both divisions
• 60 days: Establish the single source of truth, install a clear meeting and communication rhythm, and begin building KPIs and dashboards for each department
• 90 days: Roll out accountability and performance standards at the supervisory level, deliver early financial visibility, and demonstrate quick wins that build momentum
• 180 days: Own the management hat fully, with the founder freed to focus on vision, leadership operating to clear standards, and the operational foundation in place to support continued scaling

BENEFITS

• $115K to $130K base salary plus performance incentive, commensurate with experience
• Full-time W2 employment based in Illinois
• Bonus structure based on the growth of the organization is available.
• Benefits: Health Insurance
• 401K match is available up to 3%
• PTO: 2 Weeks to start + time off on your birthday
• A company vehicle is available for this position.
• Additional Office Shutdowns: Observe the standard US Holidays
• Professional Development: This role will be supported by an external Ops program that includes Ops mentorship, community, and live coaching

HOW TO APPLY

If you are interested in this position, please submit an application below.

Our team will review your application and get back to you shortly. We look forward to hearing from you!

DISCLAIMER:

Spyglass Ops is an authorized representative of Helping Hands Cleaning Service. We are an Operations Hiring Agency, working on behalf of growing businesses to find and hire Operations Positions. All of our roles are full-time, salaried, leadership positions within growing businesses. We also filter the businesses we work with, to ensure they provide long-term positions, growth opportunities, and a strong working environment and culture. Our company qualifies and interviews candidates, then connects finalists with our clients for final interviews and job offers. Our highest priority is creating win-win matches for both our candidates and clients.