Regional Chief Financial Officer (CFO) - North Region

Regional Chief Financial Officer (CFO) - North Region

Department: Corporate/Administrative

Employment Type: Full Time

Location: Chicago, IL

Compensation: $220,000 - $265,000 / year

Description

As the Regional Chief Financial Officer, you will serve as a strategic financial partner to each firm in the region, translating performance data into actionable insight and working alongside firm leadership to strengthen financial health across the portfolio. You will provide vision and stewardship over financial planning, operational finance, cash management, and M&A integration.

The ideal candidate understands that in a decentralized holding company model — where each partner firm retains its brand, leadership, and operational identity — influence is the primary currency of this role. You are not commanding a centralized finance function. You are a trusted advisor and thought partner who earns the right to drive change by building relationships, surfacing insights, and helping firm leaders think differently about their business. Your effectiveness will be measured by how well you identify financial soft spots, bring firm leaders along in understanding them, and partner to develop strategies that improve direct labor performance, contract pricing, cash collections, and overall profitability.

Reporting directly to the Region CEO, the CFO is a member of the Regional Executive Team (RET) and a peer to the CPO, COO, CTO, and firm Presidents. This role reports indirectly to the Trilon Chief Financial Officer.

Key Responsibilities

Finance Leadership

• Partner closely with the Region CEO and COO to drive financial performance across the region.
• Serve as a coach and thought partner to financial leadership at each firm; firm-level CFOs and Finance Leads carry a dotted-line relationship to this role.
• Implement Trilon Corporate and regional financial initiatives across the portfolio, working collaboratively and driving change with firm-level finance leaders.
• Represent firm and region-level interests to Trilon Corporate while ensuring alignment with enterprise-wide priorities.

Corporate Finance

• Lead all aspects of financial planning and analysis (FP&A), budgeting, forecasting, and long-term planning for the region.
• Partner with business leaders to drive performance through financial insight, scenario modeling, and investment ROI analysis.
• Own performance management through KPIs, variance analysis, and market benchmarking; support decisions aligned with growth and profitability objectives.
• Ensure accurate and timely reporting of regional performance to internal stakeholders.
• Provide recommendations to improve profitability and cash flow across the portfolio.
• Foster a culture of accountability, innovation, and data-driven decision-making.

Operational Finance

• Identify and lead initiatives to drive operational and financial improvement across the region.
• Lead implementation of Trilon processes, policies, and controls at the firm level.
• Lead the transformation of cash-to-accrual accounting for partner firms and add-on acquisitions in collaboration with local accounting teams.
• Engage directly at the firm level to help resolve issues and, when needed, temporarily fill finance talent gaps.

Cash Management

• Oversee and transform processes to drive cash flow and working capital optimization.
• Build a culture of cash management within the region in collaboration with finance and operational leaders.
• Drive and measure the Free Cash Flow metric across the portfolio.
• Lead the transformation of billing processes through technology, resourcing, and process improvement.

M&A Integration

• Implement integration playbooks and processes to ensure alignment of accounting policies, reporting structures, systems, and controls.
• Drive synergy realization tracking and reporting across functional areas.

Requirements / Qualifications

Experience and Technical Background

• 8+ years of progressive finance leadership experience, with at least 5 years in a senior executive role (Finance Director, VP Finance, or equivalent).
• Deep expertise across corporate finance, cash and treasury operations, and financial operations.
• Successful track record leading M&A financial due diligence and integration efforts.
• Strong working knowledge of GAAP, financial systems, and internal controls.
• Experience operating within a multi-entity, platform, or portfolio company environment (e.g., private equity-backed).
• Deep expertise in performance management, cost transformation, and process improvement.
• Strong acumen with ERP and FP&A tools (e.g., Adaptive, BST, Deltek, PowerBI).
• Strong proficiency with Excel is required and will be assessed during the interview process.
• CPA, CFA, or MBA preferred.

Leadership Attributes

• Ability to drive change and build buy-in across independent business units without direct line authority — this is fundamentally an advisory and coaching role as much as it is a finance role.
• Business and financial thought leadership; ability to translate complex data into clear, actionable guidance for firm leaders who are primarily operators, not finance professionals.
• Strategic thinking and planning, paired with willingness to roll up your sleeves on operational challenges.
• Collaborative partnership approach; strong interpersonal and relationship-building skills across decentralized, autonomous teams.
• Influential leadership style — you earn credibility through insight and follow-through, not positional authority.
• Strong problem-solving orientation with an ability to see the full picture while staying grounded in the details that matter.

This role is hybrid, ideally located in Chicago, Detroit, Boston or New York