Director, Finance & Strategy

About SITE Technologies

SITE Technologies is a Chicago-based Series A PropTech company dedicated to transforming facility management through innovative AI tools that enable enterprise clients to operate more efficiently. Our platform leverages drone aerial imaging, AI-based condition analysis, and expert engineer insights to provide a unified, reliable view of physical assets, replacing costly and inconsistent manual inspections at scale. Our culture is driven by innovation, collaboration, and joy, guided by core values such as solving complex challenges, practicing empathy and integrity, taking ownership, striving for excellence, and flourishing together.

Role Overview

We are developing a top-tier Finance & Strategy team, and this Director role serves as a cornerstone of that effort. Reporting as the primary partner and trusted second-in-command to the CFO, you will be responsible for leading financial planning and strategic finance functions. You will collaborate closely with the CEO, CTO, and CRO, shape our Series B fundraising story, and create analytical frameworks to transform data into smart decision-making. This role demands high autonomy, visibility, and a hybrid work mode suitable for a finance leader based in the metro-Detroit area. Responsibilities include building detailed financial models, validating unit economics, solving complex business challenges, and presenting to the executive board. A passion for AI is essential, as you will use it to accelerate your work, automate finance processes, and support business teams.

Key Responsibilities

• Lead the annual and rolling budgets including profit & loss, headcount, and cash flow forecasts.
• Develop and maintain the Long Range Plan with scenario modeling for strategic and fundraising purposes.
• Partner with accounting to manage the monthly close and deliver management reports to the CEO and board.
• Create department budgets with leaders and hold teams accountable to their financial plans.
• Own and lead the financial aspects of the Series B funding round: investor-ready models, KPIs narrative, and data room prep.
• Analyze mergers, acquisitions, partnerships, and market expansions with financial diligence and scenario evaluation.
• Construct SaaS metrics dashboards covering ARR/ACV cohorts, retention rates, customer acquisition cost, lifetime value, margins, and Rule of 40 compliance.
• Conduct pricing and packaging analyses for SaaS and services, focusing on unit economics by customer segment.
• Manage the annual and quarterly planning process including OKRs and goal tracking; maintain the finance and executive calendar ensuring alignment and accountability.
• Serve as a resource for cross-functional problem-solving on initiatives that span multiple departments.
• Collaborate with the Data & Analytics team to automate workflows and enhance data quality for finance, sales, and operations.

Additional Information

A separate Data & Analytics department exists, but this role requires comfort working hands-on with large data sets. The position is hybrid, requiring metro-Detroit presence.