Chief Financial Officer

The Chief Financial Officer (CFO) is a core executive role responsible for capital strategy, banking relationships, and the financial health of our high-velocity real estate enterprise. Operating in-office from our corporate headquarters in Yorkville, Illinois, this role is designed for a gritty, battle-tested financial leader who thrives in a fast-paced small-business environment. Fresh off ranking #1708 on the 2025 Inc. 5000 list of America's fastest-growing private companies—with a relentless drive to push even higher—our growing 40+ person team is pacing toward $120M in revenue for 2026, with a mandate to scale past $300M+ in the next 5 years.

In this role, you will work hand in hand with our executive team, including our Co-Owner and current acting CFO, during an intentional, phased transition. Rather than sitting behind a distant corporate desk, you will be the "tip of the spear" on commercial bank lines, debt covenants, and balance sheet architecture. You will directly guide and support our in-house Yorkville team—including Asset Management, our Finance Manager, and our Bookkeeper. While you are not hired for routine data entry, you must possess the small-business feistiness and practical hands-on mastery of systems like QuickBooks Online to step into the trenches whenever necessary to ensure our financial rhythm never skips a beat. 

Key Responsibilities

Capital Architecture & Banking Relations:

• Serve as the primary lead for all commercial banking relationships, negotiating credit facilities, term structures, and debt covenants.


• Systematically strengthen the company's balance sheet with its primary lender.


• Work hand-in-hand with company leadership and our Co-Owner/acting CFO to evaluate capital allocation, deal velocity, and major business investments.


• Model and de-risk our fast-moving 90-day operational cycle to maintain healthy liquidity and short hold-time economics.

Financial Operations & In-House Team Leadership:

• Direct and elevate our in-house office team in Yorkville, working collaboratively with Asset Management, the Finance Manager, and the Bookkeeper.


• Maintain complete operational agility in QuickBooks Online and core financial software—stepping in seamlessly during team vacations, transitions, or busy seasons to keep daily rhythms uninterrupted.


• Drive data integrity across internal financial dashboards, underwriting models, and reporting systems.


• Lead financial discussions during weekly strategic risk and leadership meetings, delivering clear, predictive metrics on capital pipeline health.


• Determine whether and when the company would be better served by transitioning from QuickBooks to more sophisticated financial software.


• Demonstrate a strong understanding of WIP and job costing.


• Create and manage budgets, holding staff accountable to performance against them.

Audits, Compliance & Risk Management:

• Oversee corporate insurance policies, workers' compensation audits, tax strategies, and external CPA partner relationships.


• Proactively monitor and maintain absolute compliance with all bank covenants and financial reporting mandates.


• Proactively manage and project the company’s cash flow needs weeks in advance, including the ability to create 13-week cash-flow forecasts.

Administration & Corporate Governance:

• Provide high-level executive oversight of employee benefits, company 401(k) programs, payroll, and essential administrative tasks for our 40+-person team.


• Build scalable, institutional financial processes that reduce founder reliance while preserving our agile decision-making culture.

Requirements

• Experience Scope: 10+ years of progressive financial leadership (Controller, VP of Finance, or CFO) within agile, high-growth small to mid-sized businesses.


• CPA Background: Active CPA license or equivalent deep accounting and corporate finance expertise strongly preferred.


• Banking Mastery: Direct experience managing commercial lender relationships, credit lines, bank covenants, and personal guarantee release strategies.


• Hands-On Feistiness: Strong proficiency with QuickBooks Online and core accounting software, paired with a willingness to roll up your sleeves and execute tactical workflows whenever the team needs coverage.


• In-Office Presence: Ability to work full-time in-office at our corporate headquarters in Yorkville, IL, collaborating directly with our executive and finance personnel.


• Culture Fit: High-drive, competitive mindset coupled with personal integrity, humility, and alignment with our "20-Mile March" growth discipline.
  

Benefits

• Paid Time Off: 15 days PTO (initial year).


• Paid Holidays: 7 paid holidays (New Year's Day, Memorial Day, Independence Day, Labor Day, Thanksgiving Day, Day after Thanksgiving, Christmas Day).


• Retirement: 401(k) program with Company Match up to 4%.


• Work Environment: Strong, family-first company culture with a commitment to high performance without 70-hour corporate burnout.