Jobs at Twenty

Own the company’s accounting and financial operations as its first full-time accounting hire. Build scalable, audit-ready processes; implement and optimize financial systems; manage external accounting, tax, audit, vendor, and government partners; establish expense and procurement policies; and support finance, legal, HR, office, and other cross-functional initiatives. The role requires strong startup judgment, attention to detail, systems expertise, and process automation skills.

Owns accounting and financial operations as the company’s first full-time accounting hire. Responsibilities include building scalable, audit-ready processes; implementing and optimizing financial systems; managing tax, bookkeeping, vendor, government, and audit partners; developing expense and procurement policies; and supporting cross-functional finance, legal, HR, office, real estate, compensation, cash management, and contracting initiatives.

Lead a 0->1 marketplace product: run user discovery, define MVP, launch and iterate, design workflows for human and automated participants, drive roadmap with a small engineering team, measure and improve matching, and brief executive leadership.

As Mission Deployment Lead, you will enhance product adoption within Intelligence Community users, translating mission workflows into operational usage and working with various stakeholders to ensure effective implementation.

As a Site Reliability Engineer, you'll ensure system reliability in a government environment, manage incidents, and collaborate with engineering teams on operational tasks and improvements while maintaining security compliance.

Lead the engineering organization for the Pathfinder cyber-operations platform across cloud and customer private clouds. Manage engineering managers and teams, drive org design and hiring, own technical roadmap and execution, ensure architecture coherence, quality, security, and operational discipline, and communicate progress and risks to senior leadership.

Lead a cross-disciplinary platform engineering team building shared UI components, enterprise onboarding/admin/security capabilities, and underlying infrastructure. Own the technical roadmap, run projects end-to-end, enforce quality and security standards, coordinate dependencies with feature teams, hire and develop engineers, and occasionally contribute code to unblock delivery.

Design, implement, and maintain enterprise security architecture; run vulnerability scans and penetration tests; monitor SIEM and respond to incidents; manage IAM, DLP, encryption, and endpoint hardening; ensure compliance (CMMC, SOC 2, GDPR, PCI-DSS); provide security training and incident reporting.

Design and operate AWS-based infrastructure, implement Infrastructure-as-Code with Terraform, and improve observability and reliability while collaborating with product and backend teams.

The role involves building financial models, managing budgeting and reporting, supporting fundraising, and overseeing operational systems. It seeks analytical and strategic problem solvers with finance experience.

The DevOps Engineer will design and manage AWS infrastructure, implement Infrastructure-as-Code using Terraform, maintain CI/CD pipelines, ensure security, and document systems for operational reliability.

The Mission Architect ensures products meet real user needs by translating complex workflows into clear requirements. This role involves partnering with cross-functional teams to shape product direction and validate features against operational realities.

As a Senior Frontend Software Engineer, you will build high-performance UI components using React and TypeScript, optimize for speed and reliability, and collaborate across teams to implement complex data visualizations for cyber operations.

The Senior Forward Deployed Analyst will lead cyber operations and intelligence analysis, translating operational needs into technical requirements, while engaging directly with stakeholders and enhancing cybersecurity tools with expertise in digital network exploitation.

The Staff Frontend Software Engineer will architect and build high-performance React/TypeScript applications, mentor engineers, and lead frontend technical initiatives for complex cyber operation data visualization.

Lead the development of offensive cyber capabilities, mentor junior engineers, and establish best practices for offensive tooling. Conduct research on adversary techniques and develop attack frameworks for national security initiatives.

Lead the development and operation of a data lake for cyber operations, design schemas and indexes, build and evolve ETL pipelines, mentor engineers, and drive technical initiatives.

The Forward Deployed Site Reliability Engineer ensures the reliability of a mission-critical platform, manages incident response, defines SLIs and SLOs, and liaises between engineering and government customers.

The Senior Forward Deployed Analyst will bridge cyber technologies with operational needs, perform intelligence analysis, and validate AI tools for cyber operations.

The Product Manager will drive products for offensive cyber missions, collaborating with engineers and stakeholders to define scope, manage delivery, and translate complex needs into actionable product outcomes.