Director, Finance & Strategy

Director of Finance & Strategy

At SITE Technologies, we're on a mission to revolutionize facility management with cutting-edge AI solutions that empower enterprise customers to operate more efficiently.

SITE is a Chicago-based 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 believe in innovation, teamwork, and having fun along the way.

Our core values define how our team shows up every day:

• Solve Impossible Problems
• Embrace Empathy & Integrity
• Own Your Outcome
• Do The Best Work of Our Lives
• Together We Thrive

If you're looking to be part of a fast-growing, forward-thinking team where your work makes an impact, join our team!

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 hybrid role ideal for a metro-Detroit based Finance leader who 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 your own velocity, automate recurring finance work, and help business partners across the company do the same.

What You'll Do:

Financial Planning & Analysis

• 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

Strategic Finance & Operations

• 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

Data & Analytics

• Data & Analytics is a separate function but we expect the candidate to be comfortable working with and manipulating massive amounts of data not just waiting for an output
• Partner with Data & Analytics to develop automated pipelines for recurring finance/sales/ops workflows, reducing manual effort and improving data quality

Requirements

What We're Looking For

• An experienced finance leader with 610 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

The most successful candidates also have

• Experience at a company that went through a venture fundraise (Series AC) 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

What we have to offer:

• This position is based in the Metro-Detroit area with a hybrid work schedule
• 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.

More Reasons to join SITE Technologies:

• Exciting Startup Energy Be part of an early-stage company where your work truly makes a difference.
• Collaborate with Brilliant Minds Work alongside top talent in AI, tech, and business.
• Professional Growth Expand your skills and grow your career in a rapidly scaling company.
• Hybrid and Remote Flexibility
• Great Culture We value innovation, ownership, and having fun while making an impact.