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TwentyTwentyArlington, VA

Strategic Finance and Business Operations Associate

Build and own the company's financial model, FP&A, fundraising support, and operating systems. Ideal for former bankers or strategic finance operators with 1-5 years experience seeking a high-velocity generalist role.

Salary not listed
On-site1+ YOEBusiness Operations

About the role

What You'll Own (Core Responsibilities)

The Model

  • Build and own Twenty's financial model end-to-end
  • Drive annual planning, the headcount ledger, board reporting, and the analytical engine the company uses to make decisions

FP&A & Reporting

  • Run semi-annual budgeting and ongoing headcount planning
  • Stand up the reporting infrastructure that gives every function visibility into performance
  • Translate financials into actionable insights for team leaders

Fundraising & Investor Relations

  • Partner with the Founders and VP Finance on the next fundraise
  • Build the data room and own diligence
  • Own monthly executive updates and quarterly board reporting between rounds

The Operating Cadence

  • Run the systems that keep a company moving: compensation design, offer generation, performance structure, and spend policies

Special Projects

  • Real estate, market research, vendor strategy, software procurement

Who You Are

  • 1–5 years in investment banking, private equity, or strategic finance at a top-tier startup
  • Mastery with Excel and Google Sheets; can build highly legible three-statement models with scenario modeling
  • Detail-obsessed with strong formatting and cross-functional communication skills
  • High horsepower: dives into one-page memos, board slides, and offer packages
  • Self-directed with urgency; creates own direction without waiting for instructions
  • Generalist by instinct; applies first principles across finance, hiring, contracts, and ops

Nice to Have

  • Prior background or interest in software, AI, cyber, defense, or intelligence
  • Daily user of AI tools (ChatGPT, Claude, Gemini); experience with Claude Code, Cowork, Rogo, Hebbia, or equivalent
  • Sense of humor

Benefits

  • Health: Medical, dental, and vision plan options; Life/AD&D, disability coverage
  • Family: Paid parental leave (12 weeks birthing parents, 4 weeks non-birthing, 6 weeks adoptive/foster/surrogacy)
  • Vacation: Paid holidays and flexible PTO
  • Retirement: 401(k) with pre-tax and Roth options; HSA/FSA, dependent care FSA
  • At the office: Commuter benefits, on-site garage parking, bike storage, building fitness center, desk setup stipend

Skills

Financial ModelingExcelGoogle SheetsFP&ABudgetingBoard ReportingInvestor RelationsCompensation DesignScenario ModelingThree-Statement Modeling
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