Accountant/Assistant Controller (Chicago Area)

Assistant Controller (Foundational Hire)

Location & Hours

Location: Remote-first 🌍 (Chicagoland-based, with 2 in-person days per month)

Hours: Start at ~20 hours per week ⏱️, with the ability to scale up to 40 hours per week as clients grow (or remain at 20 hours if that is the right long-term fit)

Why You’ll Love Working with Us 🚀

This is not a traditional accounting role.

We are building a modern, tech-enabled fractional finance and accounting firm for multi-location service businesses—and this role sits at the center of that build.

What makes this opportunity different:

• Remote-first and flexible by design 🌍 — We focus on outcomes, accountability, and insight, not face time or busywork.
• Real ownership and agency 🧠 — You will dig into the why behind the numbers and help shape how we deliver for clients.
• Builder energy 🏗️ — You will help design scopes of work, close processes, review standards, and how we scale delivery.
• High-impact client work 📊 — Our clients rely on their financials to make real growth and people decisions.
• True partnership with the Founder 🤝 — This is the first senior hire, working closely together to build something meaningful from the ground up.

If you enjoy combining hands-on accounting, light analysis, and building systems that others will use, this role was designed for you.

About Us:

We help multi-location service businesses ($2M–$20M in revenue) turn clean financials into confident growth decisions.

We specialize in complexity-driven, people-heavy service businesses, including:

• Consumer healthcare and wellness (MedSpas, therapy clinics, senior care)
• Home services (HVAC, trades, restoration)
• Childcare, Montessori, and enrichment programs

Our clients do not just want reports—they want clarity, location-level insight, and a finance partner who helps them grow responsibly.

We are Chicago-anchored, remote day-to-day, and meet twice per month in person for collaboration and planning.

About the Role

We are hiring an Assistant Controller as our first foundational delivery hire.

Initially, you will be deeply involved in running month-end close, preparing financial statements, and helping define how our services are delivered. As we grow, you will help hire and oversee our first bookkeeper and transition portions of the close while maintaining quality and oversight.

This role is a mix of:

• Delivering client work
• Building internal processes
• Laying the groundwork for future team leadership

What You’ll Do:

Own and run month-end close 📅

• Prepare and review accurate, timely month-end closes for multi-location clients
• Ensure proper accrual accounting, reconciliations, and classifications
• Maintain clean chart of accounts, classes, and location tracking
• Prepare core financial statements (P&L, Balance Sheet, Cash Flow)

Prepare client-facing financials and insights 📊

• Produce clear, client-ready financial reporting packages
• Identify trends, anomalies, and key drivers of performance
• Support first-level FP&A, including budget vs. actual analysis, margin insights, and cash visibility
• Participate in select client calls to walk through results and answer questions

Help build how we deliver 🧩

• Partner with the Founder to define and refine scopes of work, close timelines, and review standards
• Document SOPs, templates, and internal checklists that will scale with the firm
• Identify opportunities to standardize, automate, and improve efficiency and client experience

Support and manage bookkeepers as we grow 🌱

• Assist in hiring and onboarding the firm’s first bookkeeper
• Train bookkeepers on close processes and expectations
• Review work and provide feedback to maintain high standards
• Gradually transition close execution while retaining oversight and review

Work inside a modern tech stack 💻

• Work daily in QuickBooks Online and/or Xero
• Use tools such as Karbon, Double (Keeper), Fathom, Google Workspace, Slack, Loom, and Notion
• Communicate clearly and efficiently with clients and teammates using modern, async tools

Who This Role Is For

This role is ideal if you:

• Want to be early in building a firm, not joining something already fully formed
• Enjoy owning the close and understanding how the numbers connect to real business decisions
• Like combining detail-oriented accounting with higher-level thinking
• Are comfortable leading others, even if your prior management experience was outside of finance
• Value flexibility now, with the option to grow your role over time

What You Need to Succeed:

Experience and background

• 3 + years of accounting experience
• Public accounting, CAS/outsourced accounting, or in-house multi-entity experience preferred
• Experience with service-based businesses; multi-location exposure is a strong plus
• Solid understanding of GAAP, accrual accounting, and month-end close

Technical skills

• Advanced proficiency in QuickBooks Online and/or Xero (required)
• Strong reconciliation, cleanup, and close skills
• Ability to prepare financials that business owners can easily understand
• Exposure to basic budgeting, forecasting, or variance analysis

Leadership and working style

• Prior experience managing or supervising others (not required to be finance-specific)
• Comfortable providing feedback and setting expectations
• Organized, proactive, and comfortable working in an early-stage environment
• Curious, thoughtful, and committed to high standards

Location & Availability

• Based in the Chicagoland area (city or suburbs within ~1 hour)
• Able to attend two in-person collaboration days per month in Chicago

CPA is a plus but not required if experience is strong and relevant.

Hours, Compensation & Flexibility

• Start at approximately 20 hours per week
• Option to scale up to 40 hours per week as the firm grows
• Option to remain at 20 hours long-term if preferred
• Competitive hourly compensation, commensurate with experience

Full details will be shared during the interview process.

Why Join Now

Joining at this stage means:

• You help define the role, not just fill it
• You shape how we serve clients and build the team
• You grow alongside the firm without sacrificing life outside of work