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Fliff

Director of Finance

Posted 3 Days Ago
In-Office or Remote
Hiring Remotely in Chicago, IL, USA
Expert/Leader
In-Office or Remote
Hiring Remotely in Chicago, IL, USA
Expert/Leader
The Director of Finance owns budgeting, forecasting, accounting operations, cash flow, reporting, payroll, reconciliations, internal controls, and audit readiness. This role leads the finance and accounting team, develops scalable financial systems and processes, manages financial risks, and provides executive leadership with modeling, performance insights, and strategic analysis. The position supports high-volume transactions, wallet liabilities, vendor ecosystems, and growth initiatives in a fully remote environment.
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Fliff is the arena for high-upside play. We are dismantling the paywalls of legacy sportsbooks and reimagining the economics of social games to pioneer the next generation of rewards-driven entertainment spanning sports, casino, predictions, collectibles, and beyond.

Powered by a frictionless freemium architecture, Fliff democratizes access and gives millions of players nationwide a real stake, real thrill, and real upside. By combining authentic competitive drive with instant rewards and interactive games, we are turning passive sports fans and casual gamers into active, empowered participants – unlocking the player in everyone.


The Role:

The Director of Finance will serve as the financial anchor for Fliff, taking direct ownership of budgeting, forecasting, accounting operations, cash flow management, and internal controls. This role bridges strategic executive planning with hands-on financial stewardship, scaling our financial architecture to support rapid transactional growth, player wallet liabilities, and complex vendor/contractor ecosystems.

You will manage and mentor the finance and accounting team, partner across Product, Marketing, and Operations, and operate with high autonomy to deliver accurate, audit-ready financial insights directly to executive leadership.

Key Responsibilities:

  • Strategic Planning, Budgeting & Forecasting
  • Own the company-wide operating budget, quarterly rolling forecasts, and multi-year financial models.

  • Analyze complex financial datasets to evaluate key unit economics, player lifetime value (LTV), acquisition efficiency (CAC), revenue growth, profitability, and burn rate.

  • Partner cross-functionally with department heads to track departmental budgets, identify variances, and uncover cost-saving and ROI-enhancing opportunities.

  • Prepare comprehensive financial presentations, board packages, and key performance metric summaries for executive leadership and stakeholders.

  • Comprehensive Financial Reporting & Accounting Operations
  • Direct month-end, quarter-end, and year-end close cycles, ensuring absolute integrity across consolidated balance sheets, income statements, and cash flow statements under US GAAP.

  • Deliver accurate and timely financial reporting packages, tax documentation, and detailed bank and wallet reconciliations.

  • Oversee end-to-end Accounts Payable (A/P) and Accounts Receivable (A/R) workflows, working cross-functionally to optimize working capital and maintain vendor relationships.

  • Direct domestic and global payroll operations and contractor payment pipelines to ensure precise, timely compensation and tax compliance.

  • Internal Controls, Policies & Systems Scalability
  • Design, implement, and enforce robust internal accounting policies, standard operating procedures, and risk controls across all financial workflows.

  • Lead the implementation and modernization of scalable financial software, ERP systems, and automated reconciliation tools tailored to high-volume transaction environments.

  • Drive audit readiness, coordinating directly with external auditors, tax advisors, and banking partners.

  • Cross-Functional Leadership & Ad Hoc Strategy
  • Lead, mentor, and scale the finance and accounting function, promoting a culture of precision, accountability, and continuous improvement.

  • Serve as a self-directed partner to leadership, managing upward proactively to flag financial risks, surface trends, and deliver scenario modeling for strategic initiatives.

  • Steer ad hoc financial analyses and special projects across new market entries, payment gateway optimizations, and prize/reward structures.

  •  

What We're Looking For:

  • Bachelor’s degree in Finance, Accounting, Economics, or a related quantitative field.

  • 8–12+ years of progressive finance and accounting experience, including 4+ years of direct people management experience leading finance professionals.

  • Demonstrated mastery of financial reporting, US GAAP, and technical accounting across financial statements, reconciliations, and tax compliance.

  • Proven track record leading company-wide budgeting, rolling forecasting, and detailed variance analyses in high-growth environments.

  • Hands-on experience supervising payroll, contractor disbursements, and A/P & A/R functions at scale.

  • High autonomy as a self-starter with a demonstrated track record of managing upward and communicating effectively across non-finance teams.

  • Exceptional analytical rigor, attention to detail, and problem-solving skills with the ability to maintain accuracy under tight deadlines.

  • Experience in social gaming, sports entertainment, daily fantasy sports (DFS), fintech, or consumer tech platforms with high transaction volumes and dual-currency or wallet models
  • Preferred Qualifications
  • Active CPA, CFA, or an MBA/Master’s degree in Accounting or Finance.

  • Direct experience selecting, implementing, or optimizing modern ERPs (e.g., NetSuite) and FP&A/BI platforms.

  •  

Benefits:

  • Competitive compensation package, including base salary, benefits, and equity. 

  • Unlimited/Flexible paid time off.

  • Health benefits with 100% paid premiums* for medical, dental, and vision plans for employees and dependents, plus on-demand healthcare concierge.

  • Pre-tax savings plans for healthcare, with up to a $500 annual employer contribution to the HSA (if enrolled in the HSA medical plan).

  • Employee-sponsored 401(k) to help reach your financial goals.  

  • $500 work-from-home stipend for equipment and accessories.

  • Fully remote work environment.

  • Generous parental leave.

  • Professional development opportunities in a dynamic, global setting.

We are a multinational company with our headquarters based in Philadelphia, and offices in New York, Austin, Chicago, and Sofia, Bulgaria. Wherever we are in the world, we pride ourselves on being a close-knit, focused team that is welcoming and friendly, and the work that we do is always interesting and rewarding. Wherever we are in the world, we pride ourselves on being a close-knit, focused team that is:

Welcoming and Friendly

We want to reflect the diversity of the cities we serve. By creating an inclusive culture where everyone can thrive, we’ll make Fliff better for employees and customers alike.

Lively and Creative

We respect and value each other’s ideas, experience and expertise. There is no such thing as a bad idea; only ideas that are executed and ideas that are discarded after consideration.

Stimulating and Rewarding

We know bright minds love a challenge, and we understand your desire to see your hard work pay off. We’ll make sure your daily tasks align with your career ambitions as we grow together.

Equal Employment Opportunity Statement

Fliff is an equal-opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status.

Join Our Team!

If you're ready to be part of an exciting, innovative, and dynamic team, apply now to help shape the future of sports gaming with Fliff.


IMPORTANT NOTICE: The privacy and security of applicant information is paramount and we take fraud attempts very seriously. Please note that Fliff will never ask for payment or personal financial information during the application process. All of our legitimate job opportunities can be found on our official career site (https://www.getfliff.com/careers). Please be cautious of communications and links that come from non-company email addresses (@getfliff.com), social media messaging platforms or unsolicited phone calls.

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