Director, Finance & Strategy

About SITE Technologies

SITE Technologies is a Chicago-headquartered Series A PropTech firm aiming to transform facility management through advanced AI-driven solutions. The company provides commercial real estate owners and facility managers with a comprehensive platform that utilizes drone aerial imaging, AI-based condition assessments, and expert engineer reviews to create a trusted source of truth for physical assets, replacing costly and inconsistent manual inspections.

Core Values

• Confront and solve challenging problems
• Demonstrate empathy and uphold integrity
• Take full ownership of outcomes
• Deliver exceptional work quality
• Collaborate to succeed collectively

About the Role

SITE Technologies is establishing a premier Finance & Strategy function, with this Director position serving as a key foundation. Reporting directly to the CFO, the Director will also partner closely with the CEO, CTO, and CRO, leading the company’s financial planning and strategic initiatives. Responsibilities include developing financial models, rolling forecasts, supporting Series B fundraising efforts, and creating analytical frameworks to transform data into actionable decisions.

This is a visible and autonomous role demanding balance between strategic leadership and hands-on financial modeling and analysis. The ideal candidate will skillfully build complex models, scrutinize unit economics, tackle intricate business challenges, and communicate insights to the board and executive leadership. A genuine enthusiasm for leveraging AI to enhance productivity and automation across finance and broader teams is essential.

Key Responsibilities

• Manage the annual financial plan and rolling forecasts including profit & loss, staffing, and cash flow models
• Maintain the Long Range Plan (LRP) incorporating scenario analyses for strategic decisions and fundraising support
• Lead monthly financial close processes and coordinate management reporting for the CEO and board
• Collaborate with department leaders to establish budgets and enforce financial accountability
• Drive the financial aspects of the Series B capital raise, including investor-ready modeling, KPI narratives, and data room preparation
• Assess mergers, acquisitions, partnerships, and market expansion opportunities through detailed financial diligence and scenario modeling
• Develop and refine SaaS performance dashboards tracking ARR/ACV cohorts, gross revenue retention, net revenue retention, customer acquisition costs, lifetime value, segment profitability, and Rule of 40 metrics
• Analyze pricing and packaging strategies for SaaS and services offerings, emphasizing unit economics by customer segment
• Oversee annual and quarterly planning cycles (OKRs, goals), maintain executive operating calendars, and ensure leadership alignment and accountability
• Serve as a problem-solving resource for cross-functional initiatives that span multiple departments
• Partner with Data & Analytics teams to build automated data pipelines that streamline finance, sales, and operations workflows, enhancing accuracy and reducing manual input

Additional Information

The Director will often handle and analyze substantial datasets and must be comfortable engaging directly with data rather than depending solely on outputs. The role combines strategic insight with detailed execution in a fast-paced, growth-oriented environment.