Senior/Staff Forward Deployed Software Engineer - TS/SCI Cleared

Twenty Technologies industrializes offensive cyber operations for the U.S. and its allies, ensuring American and allied primacy in cyberspace. Founded in 2024 and headquartered in Arlington, Virginia, Twenty has raised $168M from leading investors to build mission-critical software for cyber operations in restricted, air-gapped environments.

About the role

You’ll serve as a generalist engineering presence at a government customer site, operating Twenty’s mission-critical platform in a restricted, air-gapped environment. This is the broadest engineering role at Twenty, where you’ll extend and operate applications used by operators and analysts tackling hard national security problems. Your work will span customer-specific features, data integrations, deployments, and production reliability—often in the same month. You’ll collaborate with Arlington-based specialists (e.g., data/AI engineers) for guidance but will independently own judgment calls in the field, where the office-based team cannot access. When customer work is quiet, you’ll contribute to Twenty’s core product, directly applying field insights to improve the platform. You’ll report to the VP of Engineering and work closely with forward-deployed colleagues, Arlington teams, and customer technical staff.

Responsibilities

• Customer-Specific Features & Extensions:
  • Design and build features, extensions, and integrations to adapt Twenty’s applications to the customer’s mission, workflows, and environment.
  • Work directly with customer users and technical staff to scope and deliver pragmatic solutions, balancing speed, robustness, and environmental constraints.
  • Write testable, debuggable, and maintainable code for air-gapped environments, where tests are critical for remote teammate trust.
  • Ensure code meets classified-environment security standards (e.g., no hardcoded secrets, disciplined credential handling, audit-ready practices).
• Data Integration & AI-Backed Capabilities:
  • Build extensions to retrieve, parse, transform, and load new data sources into Twenty’s applications, collaborating with forward-deployed or Arlington data engineers.
  • Investigate unfamiliar source systems and data formats with customer stakeholders to understand semantics, access patterns, and constraints.
  • Extend and field-test AI-backed capabilities with guidance from Arlington AI engineers, reporting real-world effectiveness.
• Deployment & Site Reliability:
  • Work with the customer’s deployment team to approve, deploy, and update software in the high-side environment, coordinating with Arlington engineering.
  • Monitor platform health and data flows using the LGTM stack (Grafana, Loki, Tempo, Mimir), identifying anomalies before they escalate.
  • Diagnose and resolve production issues on-site, escalating to Arlington with clear findings.
  • Drive root cause analysis and post-incident reviews, turning findings into runbooks, fixes, or design changes.
  • Participate in on-call rotations (PagerDuty), with potential on-site response for off-hours incidents due to air-gapped constraints.
• Product Engineering:
  • Build features for Twenty’s core product applications during lulls in customer-driven work, collaborating with Arlington teams.
  • Surface field patterns to advocate for platform capabilities, generalizing customer-specific work to accelerate future deployments.
• Customer & Team Liaison:
  • Serve as a consistent, professional engineering presence for the government customer, relaying operational observations and feedback to Arlington.
  • Work alongside forward-deployed engineers and analysts, sharing context and coverage across the on-site team.

Requirements

• 6+ years of professional software engineering experience, including substantial ownership of production services or applications.
• Strong generalist programming ability in Go, Python, or TypeScript, with a focus on code that remote teammates can review and extend.
• End-to-end experience building and shipping backend services or full-stack features: design, implementation, testing, deployment, and operation.
• Production debugging skills: reading logs, tracing failures across components, and root-causing issues under time pressure.
• Operational fluency: Linux command line, containerized environments (Docker, Docker Compose), and observability tooling.
• Demonstrated range: experience delivering production work outside your core specialty (e.g., data pipelines, integrations, infrastructure, ML-backed features) with specialist support.
• Experience in forward-deployed, field engineering, or embedded customer-facing roles, including deploying and operating software in air-gapped, classified, or restricted environments.
• Ability to work independently, with sound judgment about when to decide versus escalate.
• Full-time on-site work at a government facility in Northern Virginia, with travel to Arlington, VA (typically 4 days/month).
• Active TS/SCI security clearance with full-scope polygraph.

Nice to Have

• Hands-on experience building ETL/ELT pipelines (e.g., Airflow, NiFi, AWS Glue) or data integrations, with strong SQL and schema design skills.
• Experience building LLM-backed application features or operating AI/ML systems in production.
• Familiarity with observability tooling (Grafana, Datadog, Splunk).
• Experience with streaming/message queue technologies (e.g., Kafka, NATS, Kinesis, RabbitMQ).
• Background in military, intelligence, or defense contracting environments.

Skills

• Languages: Go, TypeScript, Python
• Cloud: AWS (EC2, ECS, RDS, CloudWatch) in closed enclave environments
• Containers: Docker, Docker Compose
• Observability: Grafana, Loki, Tempo, Mimir (LGTM stack)
• Alerting/On-call: PagerDuty
• Messaging: NATS
• Databases: PostgreSQL
• Data Integration: Twenty’s purpose-built data platform and integration layer

Benefits

• Health: Medical, dental, and vision plan options; life/AD&D and disability coverage.
• Family: Paid parental leave (12 weeks for birthing parents, 4 for non-birthing parents, 6 for adoptive/foster/surrogacy).
• Vacation: Paid holidays and flexible PTO.
• Retirement: 401(k) with pre-tax and Roth options; HSA/FSA and dependent care FSA.

Benefits vary by location, role, and eligibility. Full details provided during the interview and offer process.

Due to U.S. government contract and security requirements, this role is limited to U.S. citizens.