Director, Finance & Strategy Remote

Protagonist Management LLC; Chicago (IL); Hybrid; USD 180,000 - 260,000; Full time

Benefits offered by this job

Competitive salary

Stock options

Generous vacation and sick time

Holidays + floating days

Volunteer days

Parental leave

Health, dental, vision, life insurance

401K with 4% match

Hybrid & remote flexibility

Job summary

SITE Technologies, a Chicago-based AI-driven PropTech company, is seeking an experienced finance leader to be CFO’s primary partner and #2. You will own the financial planning engine, drive the Series B narrative, and build scalable analytics infrastructure across FP&A, strategy, and operations.

The role blends rigorous three-statement modeling with strategic diligence, board interaction, and cross-functional collaboration in a fast-growing startup environment.

Qualifications

• 6–10 years of progressive finance experience; background in investment banking, consulting, or corporate strategic finance is a strong plus, with at least 3 years in a SaaS or high-growth startup environment
• Deep fluency in SaaS metrics – ARR, NRR, CAC, LTV, Rule of 40
• Strong financial modeling skills (3-statement, long-range, scenario, and cohort analyses)
• Experience owning or co-owning an FP&A function, not just contributing to one
• Comfort operating as a generalist in a lean environment with board presentation ability
• Exceptional communicator who can distill complexity into crisp, actionable insight

Responsibilities

• Own the annual plan and rolling forecast for P&L, headcount, and cash-flow modeling
• Lead the monthly close cadence and deliver the management reporting package to the CEO and board
• Develop department-level budgets with functional leaders and hold the business accountable
• Lead the financial workstream for the Series B raise: investor-ready model, KPI narrative, and data-room preparation
• Build out the SaaS Dashboard: ARR/ACV cohorts, GRR/NRR, CAC, LTV, Rule of 40, etc.

Skills

SaaS metrics

Financial modeling

FP&A ownership

Board communications

Data analytics

Startup finance

AI finance tools

Tools

Claude Code

Claude Excel

Salesforce

Job description

About SITE Technologies:

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 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 believe in innovation, teamwork, and having fun along the way.

• 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!

Working at SITE Technologies:

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 – but we want to be direct: this is not a purely strategic or managerial seat. 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 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 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 for) 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 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

What we have to offer:

• This position can be based in one of 18 States where SITE is an Employer (AR, CA, CO, DC, FL, IL, MA, MD, ME, NY, NJ, OH, PA, SC, TX, UT, VA or WA) or in SITE’s Chicago Office.
• 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.