Director of Engineering

LegitScript

2d•Hybrid

About The Position

A plan is only as good as the team that can build it. At LegitScript, the Director of Engineering owns that team. You will lead through engineering managers, set the standard your squads build to, and make sure the software LegitScript promises actually ships. This is a senior technical leadership role: your judgment shapes architecture, estimates, and technical direction, but your leverage comes from the managers and technical leaders you develop, not the code you write yourself. You will own the integrity of what engineering promises. Every commitment carries an engineering manager's signature on feasibility, approach, and cost, and that signature has to hold up in delivery. You will reduce the drag of maintenance work, make technical debt visible enough to compete for priority on its own merits, and build a reliability practice that keeps on-call sustainable. You will partner as a peer with product leadership, drawing a clean line between what gets built and how it gets built, so every trade-off is a real decision instead of a surprise.

Requirements

10+ years in software engineering, including 4+ years leading engineers, with demonstrable experience leading through other managers or senior technical leaders.
A track record of delivering complex B2B software, ideally in SaaS, fintech, regtech, compliance, trust and safety, or another domain where accuracy and defensibility matter as much as speed.
Experience owning delivery across multiple teams at once, including capacity planning, forecasting, and dependency management.
Credibility on estimation, with a track record of commitments that held and a clear view of how to fix a system that produces bad estimates.
Experience partnering with a product counterpart as a peer, with a clean boundary between product intent and technical execution.
Technical depth to evaluate architecture, API and integration design, and data modeling decisions, along with the judgment to know when to defer.
Experience consuming a shared platform or paved road rather than building parallel infrastructure per team.
Strong command of reliability practice, including observability, incident response, and sustainable on-call.
Experience hiring, growing, and retaining strong engineers and engineering managers.
Excellent written and verbal communication, with the ability to explain a technical trade-off to an executive, a product partner, and an engineer in the same document.
A bachelor's degree in computer science or a related field, or equivalent practical experience.

Nice To Haves

Experience in products that combine software automation with expert human review, including human-in-the-loop decision systems.
Domain experience in payments, healthcare, pharmaceuticals, supplements, financial crime, marketplaces, or advertising platforms.
Experience delivering complex, operations- and customer-facing applications on the Salesforce platform.
Experience in an organization moving to standardized, containerized deployment, delivered incrementally rather than through a single cutover.
Experience managing external consultancies with a deliberate plan to internalize ownership.

Responsibilities

Own delivery across your squads, including capacity planning, forecasting, and clear visibility into where every commitment stands.
Stand behind the engineering side of every co-signed bet: feasibility, approach, and cost.
Sequence technical work, surface delivery risk early, and turn a slipping commitment into a decision rather than a surprise.
Set and hold the standard for engineering quality, including design review, code review, testing, and documentation.
Own reliability, monitoring, and incident response for the services your squads run, and keep on-call sustainable.
Partner with staff engineers on architecture direction, and make sure squads build on the shared platform rather than around it.
Reduce operational toil through automation, replatforming, and retirement, and make technical debt visible enough to get funded.
Lead, coach, and grow engineering managers, owning hiring, performance, and career development.
Develop tech leads and senior engineers, building a strong technical bench in every squad.
Define and track engineering health metrics, including delivery predictability, cycle time, deployment frequency, and time to recovery.
Report progress, risk, and trade-offs to engineering leadership, product, and the executive team with clarity and a clear point of view.