Multi-Entity Controller, Bruiser Companies

Bruiser's Auto; Chicago (IL); On-site; USD 100,000 - 150,000; Full time

Benefits offered by this job

401(k)

401(k) matching

Dental insurance

Health insurance

Life insurance

Paid time off

Vision insurance

Job summary

Bruiser Companies is seeking a Controller to own the financial operations of a fast-growing, multi-entity business. You will take full ownership of daily financial reality across all entities, reduce the CEO's finance workload, and build scalable reporting infrastructure for future growth.

This hands-on role demands experience with multi-entity consolidation, audits, and investor-grade reporting, plus a proactive approach to automation and AI-enabled workflows.

Qualifications

• Experience managing finances across multiple legal entities.
• Proficiency with multi-entity QuickBooks and intercompany processes.
• Strong automation mindset and data pipeline skills.

Responsibilities

• Perform daily bank and account reconciliations across all entities.
• Own monthly, quarterly, and annual close processes across multiple entities.
• Build and maintain a rolling 13-week cash forecast across all entities.
• Prepare consolidated and entity-level financial statements and board packs.
• Lead annual audits and liaise with external auditors.
• Manage lender reporting and monitor debt covenants.
• Handle intercompany transactions, eliminations, and transfer pricing.
• Develop automations and data pipelines to eliminate manual work.
• Resolve finance fire-drills quickly and prevent recurrence.

Skills

Advanced QuickBooks Online

ADP payroll GL integration

Ramp and Stripe experience

Excel advanced (Pivot, INDEX/MATCH, 3‑

Education

Bachelor's degree in accounting/finance

CPA preferred

Tools

QuickBooks Online

Ramp

Stripe

QBO API integrations

Zapier/Make

Job description

About Bruiser Companies

Bruiser Companies is a family of operating businesses generating revenue across trucking, automotive, technology services, and real estate. We move fast, we build aggressively, and we hold high standards. We are currently preparing for institutional capital and targeting significant revenue growth in the near term. Bruiser has operations in multiple states, employs more than 150 people, and is scaling toward $1 billion in top-line revenue over the next three years. This is not a stable, cruise-control environment. It's a build-phase company with real complexity and real upside.

The Role

This is a builder's seat, not a management title. Bruiser Companies is hiring a Controller to personally own the financial operations of a fast-growing, multi-entity business. You will take full ownership of the daily financial reality across all entities, reduce the CEO's finance workload materially within six months, and build the systems and reporting infrastructure a $1 billion business needs before it gets there. The right person treats financial operations the way an engineer treats production systems: accurate, automated where possible, and built to scale. You thrive in ambiguity, you build structure rather than wait for someone to hand it to you, and you'd rather fix the root cause than patch the symptom.

What You'll Do

• Perform daily bank and account reconciliations across all entities—no exceptions, no delays
• Own monthly, quarterly, and annual close processes across multiple entities
• Build and maintain a rolling 13-week cash forecast across all entities
• Prepare consolidated and entity-level financial statements, board packages, and investor-grade reporting
• Lead annual audits and serve as the primary point of contact for external auditors
• Manage lender reporting and monitor debt covenants proactively
• Handle all intercompany transactions, eliminations, and transfer pricing
• Personally build automations, scripts, or data pipelines that eliminate manual work
• Solve finance fire-drills independently and prevent recurrence

What Success Looks Like At 6 months:

The CEO is largely out of finance. Zero missed deadlines. Daily reconciliations running clean across all entities. At least two meaningful system improvements deployed. At 12 months: Audit-ready at any point in time. Investor-grade reporting live. Scalable systems built for a $50M+ business.

Key Requirements

• 5-10 years of progressive finance and accounting experience
• Direct experience managing finances across multiple legal entities (family of companies, holding company, or family office preferred)
• Advanced QuickBooks Online: multi-entity, intercompany, custom reporting
• ADP payroll GL integration and reconciliation experience
• Proficiency with Ramp, Stripe, banking portals, and lender portals
• Advanced Excel: pivot tables, INDEX/MATCH, SUMIFS, array formulas, three-statement modeling from scratch
• Active, demonstrated use of AI and LLM tools in real finance workflows (hard requirement, not a preference)
• Ability to personally build automations: Python, JavaScript, QBO API integrations, Zapier/Make workflows, or equivalent
• Comfortable operating and making sound decisions with 80-90% confidence when conditions require speed
• CPA preferred but not required if technical capability and judgment are demonstrably strong

Do Not Apply If

• You view AI and automation as a threat rather than a tool
• Your operating model depends on delegating work to external CPAs or consultants you should be doing internally
• You need detailed processes and rigid structure handed to you to function You see "Controller" primarily as a people-management title
• You have never personally performed intercompany reconciliations or eliminations across related entities

Compensation & Benefits (continued)

• $100,000-$150,000 base salary (commensurate with experience)
• Performance-based bonus
• Equity and upside participation across multiple operating entities

Pay

$100,000.00 - $150,000.00 per year

Benefits

• 401(k)
• 401(k) matching
• Dental insurance
• Health insurance
• Life insurance
• Paid time off
• Vision insurance Work Location: In person