Chief Financial Officer

Hirewell; Chicago (IL); Hybrid; USD 250,000 - 350,000; Full time

Job summary

Hirewell is exclusively retained to lead the search for a strategic, hands-on Chief Financial Officer to guide the organization through rapid growth in healthcare workforce solutions. This hybrid role is based in the Chicago area with 2 days onsite weekly.

The CFO will partner with the CEO, Board, and executive leadership to translate strategy into credible financial plans, secure resources for scale, and drive profitability and impact across B2B and B2C offerings.

Qualifications

• Finance leadership experience in a growth-oriented organization.
• Experience supporting transformation and capital initiatives.
• Direct involvement in due diligence, negotiations, and documentation for strategic partnerships or capital initiatives.
• Able to operate as a working executive with hands-on problem solving.

Responsibilities

• Develop and maintain the financial roadmap to support long-term growth and bigger revenue.
• Evaluate funding pathways, working-capital needs, and partnerships to support growth.
• Translate strategy into multiyear plans, budgets, rolling forecasts, and scenario models.
• Drive forecasting, pricing, revenue recognition, cost accounting, and working-capital analysis across models.

Skills

Finance leadership

Strategic finance

Three-statement fluency

Financial modeling

Board communication

Education

Bachelor's in Finance or Accounting

Tools

ERP systems

Financial modeling

Job description

Hirewell is exclusively retained to lead the search for a strategic, hands-on Chief Financial Officer, reporting to the Chief Executive Officer, to guide the organization through a phase of rapid growth focused on improving the quality of the healthcare industry workforce.

This is an opportunity to join an established yet innovative, impact-focused organization at a meaningful inflection point. The organization has a strong core business, proven market credibility, differentiated intellectual property, and an expanding portfolio across B2B and B2C. The organization is moving from vision to execution on several important growth initiatives, including a transformed AI-enabled workforce offering, a stronger recurring-revenue model, and expanded use of its content and data assets.

The CFO will help shape how the organization grows, secures the resources required to scale, and expands access to solutions that improve the healthcare industry workforce. The work is commercially complex, strategically important, and directly connected to better outcomes for healthcare professionals, organizations, and patients. It requires creative financial judgment around working capital, funding options, partnerships, and mission-aligned growth.

This is not a hands-off, reporting-oriented CFO role. The CFO will serve as a close partner to the CEO, Board and executive leadership team, translating strategy into credible financial plans, surfacing tradeoffs, and helping leadership understand the downstream implications of growth, product, and allocation decisions.

The right person will bring strong financial modeling, business acumen, sound judgment, and accounting leadership. They will be comfortable working with incomplete information, developing useful estimates without false precision, and helping the organization find responsible paths forward while maintaining appropriate controls, quality, and financial discipline.

This is a hybrid role based in the Chicago area, with an expectation of 2 days per week onsite.

The Role

Strategic Finance to Drive Growth, Profitability, and Impact

• Develop and maintain the financial roadmap supporting long-term growth objectives, including the path from current scale to materially larger revenue and impact.
• Help leadership identify and evaluate funding pathways, working-capital needs, and partnership options required to support growth while preserving the organization’s mission and impact focus.
• Translate strategic priorities into multiyear plans, annual budgets, rolling forecasts, and scenario models.
• Evaluate pricing, revenue models, P&L performance, product economics, margins, and investment requirements across B2B and B2C offerings.
• Help leadership assess the financial and operating implications of product, market, resource-allocation, and investment/funding decisions.
• Identify key assumptions, decision points, stage gates, and financial risks as initiatives evolve.

Executive and Commercial Partnership to Strengthen Decision-Making

• Serve as a strategic financial partner to the CEO, Board, and executive leadership team.
• Support commercial negotiations, strategic partnerships, joint ventures, and other potential transactions, bringing creative financial judgment across varied ownership models, industries, commercial structures, and revenue models.
• Lead or partner on due diligence, financial structuring, and evaluation of new business arrangements.
• Proactively support leaders and the entire team in improving their financial acumen and data-informed decision-making.
• Distill complex issues into clear recommendations and decision-ready insights.
• Shift financial conversations beyond retrospective reporting toward growth, risk, performance, and strategic choices.

Financial Modeling, P&L Visibility, and Business Insight to Support Transformation

• Drive excellence in forecasting, pricing, revenue recognition, cost accounting, and working-capital analysis across recurring-revenue, subscription, membership, licensing, platform, and other scalable commercial models.
• Ensure models accurately connect the income statement, balance sheet, and cash flow statement.
• Strengthen costing, P&L visibility, and profitability analysis across services, digital offerings, intellectual property, content, and data-driven products.
• Provide useful financial insight across multiple offerings, entities, customer segments, and revenue streams.
• Guide enhanced use of KPIs, OKRs, and performance reporting to improve accountability, decision-making, and progress against strategic goals.

Financial Foundation, Controls, and Scalable Infrastructure to Manage Risk

• Lead the finance and accounting function, including a small internal team and an external accounting partner.
• Maintain accountability for financial reporting, audit, tax, controls, regulatory compliance, and fiduciary requirements.
• Evaluate the finance operating model, systems, processes, internal capabilities, and external resources as the organization grows.
• Ensure a strong financial foundation and solid quality controls without overcomplicating the work.

What We Are Looking For

• Finance leadership experience in a growth-oriented organization, ideally under $100M, with exposure to both B2B and B2C offerings.
• Demonstrated impact supporting meaningful transformation, including organic growth, or even turnaround growth in a lean, evolving environment.
• Direct involvement in due diligence, negotiation, and documentation for strategic partnerships, commercial agreements, acquisitions, joint ventures, or capital initiatives (venture capital/VC).
• Comfortable operating as a working executive; able to move between strategic finance, hands-on problem solving, and accounting leadership.
• Strong financial modeling and three-statement fluency, with experience connecting assumptions across the income statement, balance sheet, and cash flow. Relevant models may include tech-enabled professional services, intellectual property, data, content, subscription, membership, licensing, platform, and recurring-revenue businesses.
• Strong critical thinking with the ability to anticipate downstream financial and operating implications, establish decision points, and help leadership find responsible paths forward.
• Experience developing and enhancing pricing, revenue recognition, cost accounting, forecasting, P&L management, and working-capital models.
• Board accountability and executive-level communication experience including ability to distinguish material issues from unnecessary detail and bring clear recommendations.
• Strong accounting leadership, whether through direct technical depth or effective oversight of internal and external resources.
• Genuine connection to improving the healthcare industry’s workforce and interest in using commercial discipline to expand impact.

About the Organization

Our client is a mission-driven organization advancing both the healthcare quality profession and the healthcare quality discipline.

Over the past decade, our client has evolved from a traditional professional association into a broader education, credentialing, workforce development and technology-enabled organization. Its portfolio includes membership, certification, professional development, B2B workforce solutions, and emerging digital offerings designed to improve healthcare quality, safety, and workforce capability.

Our client is now preparing to launch a technology-enabled, AI-supported evolution of its workforce offering. The new model is designed to make validated assessment, workforce mapping, and skill development more scalable and accessible, while retaining targeted expert guidance where it adds the most value. The client’s work demonstrates the measurable business and clinical impact of investing in healthcare quality, strengthening the case for broader adoption across healthcare organizations.

Hirewell and its clients are an equal opportunity (EEO) employer. We hire without regard to age, color, disability, gender, gender identity, marital status, national origin, race, religion, sex, sexual orientation, veteran status, or any other protected status.