Dir, Engineering - Pathfinder

About the Company

America is under sustained cyber attack. Our adversaries infiltrate our networks, steal our IP, and degrade the digital infrastructure that modern life runs on. They’ve learned—correctly—that those attacks rarely produce consequences.

Twenty was founded to change that, by making our adversaries think twice before they attack us. Our vision is American and allied primacy in cyberspace—a future where they cannot contest us, deterrence is assured, and the free world remains secure.

Founded in 2024, Twenty Technologies ((Use the "Apply for this Job" box below).) industrializes offensive cyber operations for the U.S. and its allies. Headquartered in Arlington, Virginia, Twenty has raised $138M from Accel, Caffeinated Capital, Friends & Family Capital, Point
72 Ventures, General Catalyst, and In‑Q‑Tel.

You will own the engineering organization for Pathfinder—Twenty's core cyber operations platform, deployed across both Twenty's cloud and customer private cloud environments. You will lead a set of engineering managers and their teams spanning platform infrastructure, enterprise capabilities, and the full suite of customer‑facing Pathfinder features. You are ultimately accountable for the technical success of the product.

This is not a role for someone who manages from a distance. You'll need the architectural judgment to engage credibly with senior ICs on hard technical problems, the organizational instincts to structure and scale a growing engineering org, and the execution discipline to keep multiple teams moving in parallel against a demanding roadmap.

You’ll partner closely with the Pathfinder Product Manager on roadmap and priorities, and with the VP of Engineering on org strategy and hiring. Day to day, you’ll supervise and develop your engineering managers, balance capacity across teams, resolve cross‑team dependencies, and drive the structural decisions—team composition, scope boundaries, sequencing of splits—that determine how the Pathfinder engineering org scales.

• You lead through managers: you develop them, hold them accountable, and build the systems that let them succeed independently.
• You have the technical depth to engage meaningfully on architecture and design with senior ICs—you don't need to write the code, but you need to understand it.
• You think at the org level: headcount, team structure, scope boundaries, and sequencing are as natural to you as roadmap and delivery.
• You execute with rigor and communicate with clarity—up to VP and across to peers, without losing the technical truth.
• You thrive in hybrid deployment environments: you understand the operational complexity of software that lives both in cloud and on customer-controlled infrastructure.
• You hold a high bar and create the conditions for others to meet it—through clarity, coaching, and accountability.
• You bring calm, structured decision‑making to ambiguous, fast‑moving problem spaces.

• Own engineering execution across the Pathfinder product: delivery, quality, and technical accountability across all teams.
• Lead, develop, and hold accountable a set of engineering managers; build their capacity to run their teams independently.
• Drive org design decisions: team scope, composition, sequencing of team splits, and addition of new management capacity as the org grows.
• Balance engineering capacity across teams; make explicit prioritization calls when demand exceeds supply.
• Own the technical roadmap in partnership with the Pathfinder Product Manager, who owns the product and feature roadmap.
• Engage at the architecture level with senior ICs—reviewing designs, providing guidance, and ensuring technical coherence across the platform.
• Supervise hiring across all Pathfinder engineering teams: set the bar, calibrate across managers, and close strong candidates.
• Partner with the VP of Engineering on org strategy, headcount planning, and cross‑product engineering initiatives.
• Communicate clearly to senior leadership on progress, risks, and tradeoffs across the Pathfinder roadmap.
• Ensure engineering practices—security, quality, reliability, and operational discipline—meet the standards required for mission‑critical deployments.