Dir, Engineering - Pathfinder

Twenty•Washington, DC

20h•$224,000 - $470,000•Onsite

About The Position

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.

Requirements

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.
You have a track record of owning engineering execution across multiple teams simultaneously, with high quality and clear accountability.
You have the architectural judgment to engage credibly with senior ICs: reviewing designs, identifying risks, and providing technical guidance across a complex, multi-layer stack.
You've owned org design decisions: team structure, scope boundaries, and how to sequence growth as headcount scales.
You've managed engineering organizations serving both cloud-hosted and on-premises or customer-controlled deployment environments.
You've partnered with product managers to translate operational requirements into technical roadmaps and delivery plans.
You've supervised hiring across multiple teams: setting the bar, calibrating across managers, and running a structured, high-signal process.
You must be eligible to obtain a U.S. Government security clearance.

Nice To Haves

You have experience in defense, intelligence, or national security technology environments.
You've led engineering organizations building operational platforms for government or mission-critical customers.
You've worked with graph databases or graph-based modeling for complex analytical problems.
You've led teams shipping enterprise features: multi-tenancy, RBAC, audit logging, or similar.
You have experience with secure development practices for government or controlled environments.
You've scaled an engineering organization through a rapid growth phase, including adding management layers.

Responsibilities

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.

Benefits

Medical, dental, and vision plan options.
Life / AD&D, disability coverage options.
Paid parental leave for eligible full-time employees.
12 weeks for birthing parents, 4 for non-birthing parents, 6 weeks for adoptive, foster, or intended parents through surrogacy.
Paid holidays and flexible PTO.
401(k) with pre-tax and Roth options.
HSA/FSA options, dependent care FSA.
Commuter benefits.
On-site garage parking.
Bike storage.
Building fitness center.
Desk setup stipend.