Director of Finance

Level :
Senior Level (Member of the leadership team)

Location :
Chicago, IL

Clearbox Decisions, Inc., creators of the Cloverpop Decision Intelligence platform, is transforming enterprise decision‑making. Each year, tens of billions of dollars are lost or wasted because of bad decisions, and we’re here to fix that. Through our software platform, Cloverpop ( ), we bring together the “art” and “science” of decision making by providing enterprise customers with the ability to automate, collaborate, track, and learn from decisions.

Thanks to our proven technology and process, we bridge the data to decision disconnect, remove human biases, increase stakeholder buy‑in, and drive decision speed and quality. We are a venture‑backed start‑up led by experienced entrepreneurs and thought leaders in the space of decision intelligence, behavioural science, AI, and the future of work. Our clients include Fortune 100 companies in the consumer goods, pharmaceutical, and technology industries.

As the Director of Finance and Operations, you will play an integral role within the organization, establishing and leading the finance function and scaling up critical operations across the company, including HR, Strategic Planning, etc. This position will work closely with the executive leadership team as well as the board of directors and our investors.

As the Director of Finance and Operations, you will be the founder of our organization’s finance and operations functions. The processes and reporting capabilities you will establish will be critical to the organization’s strategic planning, decision‑making, and realization of our long‑term vision. The capabilities you build will help shape and define our go‑to‑market strategy, ways of working, and talent strategy.

• Advise the CEO on topics related to strategy development, opportunities to increase shareholder value, deploy and conserve capital, and mitigate our operational risk.
• Represent the organization's Finance, HR, and Operations interests in leadership team deliberations.
• Own budgeting, financial planning, and long‑range strategic modeling.
• Partner with the CEO on investor relations and lead reporting activities, including materials required for board meetings.
• Coordinate, prepare, and review monthly, quarterly, and annual company performance reporting.

• Direct all aspects of accounting operations, overseeing all transactions related to the general ledger, receivables, payables, payroll, and financial reporting.
• Develop accounting policies and ensure records are maintained in accordance with generally accepted accounting principles.
• Own all budgeting, forecasting, and annual audits.
• Oversee all aspects of accounting and tax policy.
• Oversee and execute all aspects of contract‑to‑invoice, AR, and AP.
• Handle all company insurance matters to ensure compliance.
• Oversee all full‑time and contracted personnel related to the function(s), including but not limited to contracted bookkeeper, Insurance Agent, Tax advisor, etc.

• Participate closely in contract pricing, negotiations, and related commercial decisions.
• Work with Commercial and Product teams to develop an optimal pricing strategy for existing and new offerings.
• Ensure MSA’s and other related agreements are in place and up to date.
• Work with the Sales and Decision Success team to translate high‑level forecasts into account plans.
• Own and drive gross margins through understanding and effective management of COGS.
• Oversee bookings and ARR regarding policy, consistency, and accuracy.
• Manage and execute commissions in partnership with leadership.
• Advise leadership on potential partnership opportunities, assessing potential commercial value, risks, and opportunities for success.

• Oversee all aspects of HR, including implementation and execution of company policy, compensation, and recruiting strategy.
• Establish CLX compensation strategy, defining levels and pay bands across various functions.
• Manage the new resource approval process and support hiring managers in the process.
• Establish a new hire onboarding process, periodic performance reviews, employee…