Director, Finance & Strategy Remote

SITE Technologies • Vernon Hills, IL

2d • Remote

About The Position

SITE Technologies is a Chicago-based Series A Prop Tech company that is redefining how commercial real estate owners and facility managers make capital planning decisions. SITE’s platform combines drone-based aerial imaging, AI-powered condition-analysis, and engineer-reviewed insights to give customers a single source of truth for their physical assets - replacing costly, inconsistent manual inspections at scale. We are building a best-in-class Finance & Strategy function, and this Director role is the cornerstone of that build. You will be the CFO’s primary partner and trusted #2, owning the financial planning and strategic finance engine of the company. You’ll work directly with the CEO, CTO, and CRO, drive our Series B financial narrative, and build the analytical infrastructure that turns data into decisions. This is a high-visibility, high-autonomy role where the ideal candidate is equally comfortable building a detailed three-statement model from scratch, pressure-testing a unit economics assumption, or rolling up their sleeves on a complex business problem as they are presenting to the board or advising the executive team. We also expect this person to be genuinely passionate about AI - using it extensively to increase their own velocity, automate recurring finance work, and help business partners across the company do the same.

Requirements

• An experienced finance leader with 6–10 years of progressive finance experience; a background in investment banking, management consulting, or corporate strategic finance is a strong plus, with at least 3 years in a SaaS or high-growth startup environment
• A genuine drive to build an AI native finance using best-in-class tools (Claude Code, Skills, Claude Excel, etc.) to meaningfully compress modeling, reporting, or analysis timelines
• Deep fluency in (and passion of) SaaS metrics - ARR, NRR, CAC, LTV, Rule of 40
• Strong financial modeling skills (3-statement, long-range, scenario, and cohort analysis)
• Experience owning or co-owning an FP&A function, not just contributing to one
• Comfort operating as a generalist in a lean environment - you can write a board memo, build a model, and present to a CRO in the same week
• Exceptional communicator who can distill complexity into crisp, actionable insight

Nice To Haves

• Experience at a company that went through a venture fundraise (Series A–C) and understands the investor diligence process
• Familiarity with mixed SaaS/professional services business models and the gross margin and revenue recognition nuances they create
• Exposure to revenue operations or GTM analytics (Salesforce data, pipeline modeling, commission plan design)
• Prior experience managing or mentoring junior finance staff

Responsibilities

• Own the annual plan and rolling forecast, including P&L, headcount, and cash flow modeling
• Build and maintain SITE’s Long Range Plan (LRP) with scenario planning capabilities for strategic decision making and fundraising support
• Lead the monthly close cadence in partnership with our accounting team, owning the management reporting package delivered to the CEO and board
• Develop department-level budgets with functional leaders and hold the business accountable to them
• Lead the financial workstream for the Series B raise: investor-ready model, KPI narrative, and data room preparation
• Evaluate M&A, partnership, and market expansion opportunities through rigorous financial diligence and scenario modeling
• Build out our SaaS Dashboard: ARR/ACV cohorts, GRR/NRR, CAC, LTV, gross margin by segment, Rule of 40, etc.
• Drive pricing and packaging analysis across our SaaS and services offering, including unit economics by customer segment
• Own the annual and quarterly planning process (OKRs, goal-setting), maintain the finance/executive operating calendar, and ensure the leadership team stays coordinated on priorities and accountable to them
• Act as go-to for cross-functional problem solving - taking on projects that don’t fit cleanly in one department
• Partner with Data & Analytics to develop automated pipelines for recurring finance/sales/ops workflows, reducing manual effort and improving data quality

Benefits

• Competitive salary
• Opportunity to participate in SITE’s stock options plan
• Generous paid vacation
• Separate sick time banks
• Ten (10) Company holidays off each year plus two (2) floating holidays
• Two (2) paid days each year to do volunteer work
• Paid parental leave benefits available after ninety (90) days of employment
• Employee health, dental, vision, life and short-term disability coverage at no cost on the first of the month after your hire date
• 401K plan with a 4% employer safe harbor contribution

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed