Multi-Entity Controller, Bruiser Companies

Bruiser's Auto · Chicago, Illinois
📅 Posted today📍 Chicago, Illinois🏢 On-site💰 $100,000 – $150,000
📍 Location
Chicago, Illinois
Open in Google Maps →
About the job

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 Full posting: https://www.indeed.com/viewjob?jk=c9dff474390d8301
About the company
Bruiser's AutoB
Bruiser's Auto
Chicago, Illinois
🔎 View company & find hiring managers →
Ready to apply?

Takes a minute — just your name, email, and résumé.

Posted by
Gus Cawley, CPA
Gus Cawley, CPA
President
Your point of contact for this role
✉ Messagein LinkedIn ↗
NorthPoint Search GroupPowered by NorthPoint Search Group
© 2026 Zipapply LLC. 100X Recruiting is a division of Zipapply LLC. All rights reserved.
Terms  ·  Privacy