Controller

What You'll Own (Core Responsibilities)

• Own Accounting and Financial Operations: Lead all accounting functions, from annual to day-to-day workflows, ensuring accuracy, efficiency, and timeliness. You will own the procure-to-pay lifecycle.
• Build for Scalability: Identify, propose, and implement solutions to automate and optimize processes. Work with our team to maintain (or reduce) overhead requirements, even as transaction volumes 10x.
• Future Audit Readiness: Prepare Twenty for future audits by building the required roadmap and timing of all necessary requirements.
• External Management: Manage and build relationships with all external partners, including tax, bookkeeping, vendors, government partners, and auditors.
• Systems Optimization: Explore and implement tools like Ramp AI and API connections between internal systems to streamline workflows.
• People & Policy: Develop internal processes, such as expense and procurement policies; build strong relationships with company leaders, as well as trust with all employees.
• Special Projects: Support a range of initiatives, which may include real estate planning, variable compensation analysis, cash management policies, and contracting.
• Treasury: Monitor corporate cash balances and manage treasury movements to ensure the company remains optimized across liquidity and yield.
• Cross-Functional Support: Step outside the normal job description to own key workflows that help a cross-functional team scale rapidly—e.g., assisting with Sales Ops, Legal, HR, and Office operations.

Qualifications

• Accounting Experience: 8+ years of accounting experience, including time in Big 4 (or equivalent) audit and high-growth technology startups.
• Government Contracts Experience: Experience with DCAA compliance and government contracts.
• Credentials: Current or former CPA is favored, but not required.
• Execution-Oriented: You believe that what sets high-performing teams apart is their ability to execute.
• Highly Detail-Oriented: You believe that formatting is a valuable tool for cross-functional communication, not a burden. You sweat the details because you know they matter.
• Concise Communication: Ability to distill information for executive audiences.
• Prioritization: You understand the operational realities of a high-growth startup, knowing when speed must beat perfection and when a task is more efficient handled manually.
• Financial Systems Expertise: Experience implementing and managing modern financial systems (e.g., ERP, spend management, payroll platforms) is required. Mastery with Excel and Google Sheets.
• Self-Propelled: You know what an excellent accounting function looks like, identifying gaps and filing them without waiting for instructions. You thrive in the unstructured environment of an early-stage company.
• Future-Oriented: You are eager to explore and implement new technologies (e.g., AI workflow/productivity tools).

Nice to Have

• Defense or Cyber Background: Prior background in the defense technology or cybersecurity industries, or similar revenue / expense structures.
• Specific Systems: Familiarity with Campfire and Ramp.
• Sense of Humor: Nano Banana image generation ability.

Benefits

• Health. Medical, dental, and vision plan options. Life / AD&D, disability coverage options.
• Family. Paid parental leave for eligible full-time employees. 12 weeks for birthing parents, 4 for non-birthing parents, 6 weeks for adoptive, foster, or intended parents through surrogacy.
• Vacation. Paid holidays and flexible PTO. Take what you need.
• Retirement. 401(k) with pre-tax and Roth options. HSA/FSA options, dependent care FSA.
• At the office. Commuter benefits. On-site garage parking. Bike storage. Building fitness center. Desk setup stipend.