Director, Software Engineering

About the role

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 (www.twenty.io http://www.twenty.io) industrializes offensive cyber operations for the U.S. and its allies. Headquartered in Arlington, Virginia, Twenty has raised $168M from Khosla Ventures, Accel, Caffeinated Capital, Friends & Family Capital, Point72 Ventures, General Catalyst, and In-Q-Tel.

Mission | On Site | Full Time | U.S. Citizenship Required / No Active Clearance Required

ROLE SUMMARY

You will own the engineering organization for our flagship analyst product — 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 product 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 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 this engineering org scales.

WHAT YOU'LL DO

- Own engineering execution across the 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 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 engineering teams: set the bar, calibrate across managers, and close strong candidates.