Director, Software Engineering - twenty

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.
• 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 roadmap.
• Ensure engineering practices—security, quality, reliability, and operational discipline—meet the standards required for mission-critical deployments.

WHO YOU ARE

• 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.

MUST HAVE

• You have 8+ years of professional software engineering experience.
• You have 5+ years of engineering management experience, including at least 3 years managing other engineering managers.