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Technical Chief of Staff

CloakedNew York, NYEngineering
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Salary
$200K - $220K USD
Job type
Full-time
Posted
29 Sept 2026
Status
Open · checked 7d ago

About this role

Cloaked is seeking a Technical Chief of Staff to join the team in New York, NY, serving as a critical partner to engineering leadership. This full-time hybrid position suits an experienced builder with deep technical expertise who can act as a proxy for leadership in architecture, engineering, and AI initiatives.

Role Overview

This position is designed for a hands-on engineer who wants founding-engineer scope combined with leadership-level reach. Working directly with the Co-founder, CTO, and Head of Engineering, the professional in this role will unblock decisions, represent the engineering department in critical discussions, and write or review code. Success in this capacity means engineering leaders can focus on high-level strategy while trusting this role to carry technical standards forward.

Key Responsibilities

Own the review, testing, and release pipeline for the CTO's hands-on output and build repeatable infrastructure for the wider team.
Act as a proxy for engineering leadership during technical discussions, AI reviews, and cross-functional meetings.
Parachute into ambiguous or stuck initiatives to identify roadblocks and implement solutions.
Read and write code, prototype ideas, review pull requests, and evaluate designs directly.
Translate leadership vision into actionable execution while maintaining a high bar for security and privacy.
Run point on high-priority engineering and AI efforts, ensuring seamless communication across product, operations, and executive teams.

Requirements

Strong engineering background with a proven history of shipping real software.
Ability to read codebases, evaluate complex architectures, and contribute code directly.
Rigorous approach to code review and testing with a focus on building scalable tooling.
Strong technical judgment capable of standing in for engineering leadership with credibility.
High comfort with ambiguity, full ownership, and running toward messy problems without waiting for instructions.
Excellent communication skills to bridge deep technical details with executive-level strategy.
High discretion when handling sensitive strategy, personnel decisions, and security data.

Nice to Have

Experience with AI and ML systems.
Familiarity with Modal or similar compute infrastructure.
Background in security or privacy domains.
Prior experience in a chief of staff, founding, or early-stage engineering role.

Skills and Tools

Software engineering and code review
Architecture and system design
AI and machine learning concepts
Release pipeline and infrastructure automation
Technical communication and strategic planning

Salary and Benefits

Annual salary range of $200,000 to $220,000 in USD, plus equity and bonus.
Comprehensive medical, dental, and vision insurance with the majority of employee premiums covered.
Company-paid basic life insurance and a 401(k) plan with company match.
Competitive paid time off including PTO, floating holidays, and sick days.
Paid parental leave for all new parents.
Monthly wellness and meals stipend alongside a home office stipend and company laptop.
Unlimited professional development fund and support for attending industry conferences.

About the Company

Cloaked builds digital safety and privacy tools designed to protect personal data, identities, and communications. Backed by a Series B funding round, the company provides masked contact details, data broker removal services, and AI-driven call screening for individuals, families, and businesses. The New York office operates in a hybrid model featuring modern kitchen spaces, regular team outings, and social events.

How to Apply

Interested candidates should visit the official Cloaked careers page to submit an application for this role.

Questions candidates ask

What is the salary for the Technical Chief of Staff role?

The salary ranges from $200,000 to $220,000 per year, complemented by equity and bonus opportunities.

Where is this job located?

This position is based in New York, NY, operating on a hybrid work model out of the company's office.

Is this a project management position?

No, this is a technical role intended for an engineer who can review code, evaluate architecture, build prototypes, and act as a technical proxy for leadership.

What benefits are provided for full-time employees?

Full-time employees receive medical, dental, and vision coverage with most premiums covered, company-paid basic life insurance, a 401(k) with company match, competitive PTO, parental leave, wellness and meal stipends, and an unlimited professional development fund.

What department does this role belong to?

This role sits within the Engineering department, working closely with the Co-founder, CTO, and Head of Engineering.

Ready to apply?

The application is on the official Cloaked careers page.

Apply on company site