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Cloaked is a Series B-funded cybersecurity and privacy company protecting 10M+ identities through masked communications, data removal, and AI-powered call screening. The company serves 600k+ paying members and has removed 1B+ records from data brokers.
As Technical Chief of Staff, you'll be a force multiplier for the engineering leadership team, working closely with the Co-founder/CTO and Head of Engineering. This is a hands-on technical role—not project management—requiring someone technical enough to represent leadership in engineering, architecture, and AI discussions, make or unblock decisions, and then build or dig into details yourself.
Key responsibilities:
- Own the review, testing, and release pipeline for the CTO's work, building repeatable infrastructure and extending it across the team
- Act as a proxy for engineering leadership in technical discussions, architecture reviews, AI roadmap discussions, and cross-functional meetings
- Parachute into ambiguous or stuck initiatives, diagnose the problem, and either solve it or bring in the right people
- Stay hands-on: read and write code, prototype ideas, review PRs and designs
- Translate leadership's vision into team execution while maintaining alignment on priorities, technical direction, privacy, and security standards
- Run point on engineering's most important initiatives, including AI efforts; prep leaders for key decisions and ensure follow-through
- Represent engineering and AI with product, ops, the exec team, and external partners
You'll work in a hybrid model from NYC (two floors with state-of-the-art kitchens and amenities). The role offers flexible remote work as needed.
Requirements:
- Strong engineering background: shipped real software, can read codebases, evaluate architecture, and contribute code
- Rigor in code review and testing; ability to build tooling so quality doesn't depend on you alone
- Technical judgment to be taken seriously as a stand-in for engineering leadership, with trust-building instincts
- Comfort with ambiguity and full ownership; ability to run at messy problems without waiting for direction
- Excellent communication: fluent between deep technical detail and executive-level framing
- High discretion: will see sensitive strategy, data, people decisions, and security matters (critical at a privacy company)
- Bonus: experience with AI/ML systems, Modal or similar compute infrastructure, security/privacy domains, or prior chief-of-staff, founding, or early-stage engineering roles
