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Director, Software Engineering

Twenty · Arlington, VA · On-site

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About Twenty

The #1 Open Source CRM for modern teams. Modular, scalable, and built to fit your business. Backed by Y Combinator.

About the role

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.

What they're looking for

  • 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
More about this role

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 ) 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

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...

Read the full posting on Twenty's site ↗

Engineering

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