Note: The job is a remote job and is open to candidates in USA. SITE Technologies is a Chicago-based Series A Prop Tech company that revolutionizes facility management with AI-driven solutions for commercial real estate. The Director of Finance & Strategy will be the CFO’s primary partner, responsible for financial planning, strategic finance, and building analytical infrastructure to support decision-making and fundraising. This role involves hands-on financial modeling, leading the Series B financial narrative, and leveraging AI to enhance financial operations.
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
Skills
- 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
- 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
Benefits
- A competitive salary plus the opportunity to participate in SITE’s stock options plan.
- Generous paid vacation and 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 available on the first of the month after your hire date.
- 401K plan with a 4% employer safe harbor contribution.
- A strong workplace culture with a smart, collaborative team.
- Hybrid and Remote Flexibility
Company Overview