Director, Financial Planning & Analysis (Finance)

Job Description
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. 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.

Capital Architecture & Banking Relations

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

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.

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% .
Strong, family-first company culture with a commitment to high performance without 70-hour corporate burnout.