VP of Finance

Woolf; Chicago (IL); Remote; USD 120,000 - 180,000; Full time

Job summary

An established industry player is on the lookout for a Vice President of Finance to lead their financial operations. This role is crucial in shaping the financial strategy and scaling processes as the organization prepares for its next growth phase. You will work closely with the CEO and a dynamic team, overseeing all aspects of financial management, including AR, AP, and cash flow. If you thrive in fast-paced environments and have a proven track record in financial leadership, this is an exciting opportunity to make a significant impact in a rapidly growing startup.

Benefits

Competitive Compensation

Fully Remote Work Environment

Flexible PTO

Company Laptop

Qualifications

• 10+ years in financial management in a high-growth environment.
• Experience leading Series A fundraising and managing complex financial models.

Responsibilities

• Oversee monthly financial close and ensure timely reporting.
• Manage customer relationships and address financial inquiries.

Skills

Excel

Google Sheets

QBO (QuickBooks Online)

Analytical Skills

Communication Skills

Education

MBA

Management Consulting Experience

Tools

Financial Modeling

Cash Flow Management

Financial Reporting

Job description

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About Woolf

Woolf is a pioneering force in university education, backed by leading Silicon Valley investors. Our mission is to reshape the future of learning by expanding access to high-quality education on a global scale. Learn more at Woolf University.

About Woolf

Woolf is a pioneering force in university education, backed by leading Silicon Valley investors. Our mission is to reshape the future of learning by expanding access to high-quality education on a global scale. Learn more at Woolf University.

We're a rapidly growing university startup, already enrolling over 10,000 degree students from around the world. With a globally distributed, primarily remote team, we thrive on collaboration across diverse locations, perspectives, and expertise.

The Opportunity

Woolf is seeking a Vice President of Finance with a CPA or CFA certification to lead and scale our finance operations. As the finance lead in a fast-growing startup, you will play a critical role in shaping Woolf's financial strategy, scaling processes, and preparing the organization for its next stage of growth, including a Series A fundraising round.

This position requires a strategic thinker with deep expertise in global financial operations and a proven ability to build and scale finance teams in dynamic, fast-paced environments. The ideal candidate will thrive on high-stakes challenges, bringing rigor and vision to Woolf's financial function while collaborating with a global, distributed team.

Team

As VP of Finance, you will report directly to the CEO and work closely with other members of the executive team and the New Business team. You will lead the finance team, which will grow under your leadership, to support Woolf's operations across multiple countries and currencies.

You will step in role with a well-defined process. There is a monthly cycle with weekly cash reporting and booking reporting against monthly targets; you will oversee all AR and AP, the financial close package, and provide regular updates and reporting against the company financial model. You will own FP&A and the company financial model with the CEO.

You will have or hire 1 or more direct reports in 2025 to support AR and AP, and cross-functional support until then.

Working Hours: Must have 6 or more hours of overlap with US Pacific Timezone (PST).

Start Date: Immediate

Responsibilities

• Customer-Facing Financial Operations (AR)
• Oversee and implement all financial operations related to monthly invoicing, ensuring compliance with complex contractual terms
• Manage customer relationships by addressing and resolving any billing or financial inquiries in a timely and professional manner
• Financial Close (Accounting)
• Lead the monthly financial close process, ensuring accuracy and timely reporting
• Financial Modeling (FP&A)
• Update and maintain the financial model to support strategic decision-making and business forecasting
• Update the customer weekly booking report against monthly projections
• Oversee staff planning updates and their alignment with financial forecasts
• Cash Flow Management
• Produce weekly cash flow reports across multiple currencies and legal entities
• Monitor bank accounts and ensure adequate cash reserves for operational needs
• Vendor & Budget Management (AP)
• Serve as the primary liaison for all vendors, negotiating cost-effective and values-aligned alternatives
• Prepare and monitor annual budget figures for operating expenses
• Financial Reporting
• Generate quarterly financial and cash flow reports for the Board of Directors
• Reconcile monthly activity and produce financial statements, working closely with other operational stakeholders
• Process Excellence
• Design scalable bookkeeping and financial processes to support a rapidly growing organization
• We may overhaul our invoicing system in 2025, using Stripe Billing or similar
• Maintain organized, up-to-date, and accessible financial files
• Collaborate with operations and data teams to build cross-functional efficiency and ensure data accuracy
  
  
  

Requirements

Certification Required: CFA or CPA.

Education: MBA or management consulting experience (BCG, McKinsey, Bain, or Big Four).

Experience:

• 10+ years in financial management, accounting, or bookkeeping, preferably in a high-growth or startup environment
• Proven experience in leading Series A or later-stage fundraising efforts, including due diligence and investor relations
• Proven ability to manage complex financial models and processes, including FP&A
• Proven ability to oversee AP/AR, financial close, and cash flow processes
• Proven ability to handle inter-company eliminations with multi-currency and international financial operations is required
• Ability to manage complex booking to amortization schemes with accuracy and GAAP compliance
  
  
  

Skills:

• Advanced proficiency in Excel, Google Sheets, and accounting tools like QBO (QuickBooks Online)
• Strong analytical skills and attention to detail
• Ability to effectively manage multiple projects and meet tight deadlines
• Exceptional communication and interpersonal skills.
  
  
  

What Makes You Stand Out:

• Experience in high-growth startups or early-stage organizations
• Proven ability to design and implement scalable financial processes
• Highly self-motivated, comfortable working in a remote-first environment, and enthusiastic about tackling challenges head-on
• Operationally focused with a hands-on approach to problem-solving
  
  
  

Benefits

• Competitive Compensation
• Work-from-home: Enjoy the flexibility of a fully remote work environment, along with flexible PTO and working hours
• Tools for Success: We provide you with a company laptop and the resources needed to succeed and grow within your role

Seniority level

• Seniority level

  Director

Employment type

• Employment type

  Full-time

Job function

• Job function

  Finance

• Industries

  IT Services and IT Consulting

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