Technical Chief of Staff

Cloaked is building a cyber expert at your side - one that watches, advises, and acts to keep you safe and private in the age of AI. 600k+ paying members already use Cloaked to take back control of their data, their identity, and who can reach them: masked emails, phone numbers, and payment cards, data removal from broker sites, and an AI voice agent that screens calls before they ring through. We've protected 10M+ identities, screened 50M+ calls, and removed 1B+ records from the data brokers who profit off personal information. Backed by a $375M Series B, we're now building the agents that turn detection into action - for individuals, families, and the companies that want to protect their people. About the role We're looking for a Technical Chief of Staff to be a true force multiplier for our engineering leadership team. You'll work in close partnership with our Co-founder/CTO, Head of Engineering, and across the engineering function as a whole. This isn't a project-management or ops role - it's for an engineer technical enough to represent leadership in engineering, architecture, and AI discussions, make or unblock decisions in the room, and then go build or dig into the details yourself. One day you're representing leadership in a design review or AI roadmap discussion, the next you're reviewing and testing code, writing a prototype, or chasing down the root cause of a cross-team problem. Success means our engineering leaders spend less time in meetings and more time on what only they can do, trusting you to carry their judgment and standards forward. If you're a builder who wants founding-engineer scope with leadership-level reach, come build with us! What you’ll do? Own the review, testing, and release pipeline for the CTO's hands-on work - build it as repeatable infra, then extend it to the rest of the team. This is a core part of the role. Act as a proxy for engineering leadership in technical discussions, architecture and AI reviews, and cross-functional meetings - conveying their thinking, making judgment calls, and committing the org to decisions. Parachute into ambiguous or stuck initiatives, figure out what's actually going on, and either solve it yourself or bring in the right people. Stay hands-on - read and write code, prototype ideas, and review PRs and designs rather than just tracking work. Translate leadership's vision into what teams execute, keeping priorities, technical direction, and our high bar for privacy and security aligned. Run point on engineering's most important initiatives, including AI efforts - prep leaders for key decisions and follow up so nothing falls through the cracks. Represent engineering and AI with product, ops, the exec team, and external partners, and bring signal back. What skills and experiences will help you? Strong engineering background - you've shipped real software and can still read a codebase, evaluate an architecture, and contribute code when it counts. Rigor in code review and testing - you catch what others miss and build tooling so quality doesn't depend on you alone. The technical judgment to be taken seriously as a stand-in for engineering leadership, and the trust-building instincts to actually be one. Comfort with ambiguity and full ownership - you see a messy problem and run at it without waiting to be told how. Excellent communication - you move fluidly between deep technical detail and clear executive-level framing. High discretion - you'll see sensitive strategy, data, people decisions, and security matters, which is especially critical at a privacy company. Bonus: experience with AI/ML systems, Modal or similar compute infra, security or privacy domains, or prior chief-of-staff, founding, or early-stage engineering roles. What do we like? Builder first. You’d rather ship the fix than write the memo about it. High agency. You run at messy problems without waiting to be told permission. Automates the repeatable. You turn one-off reviews and tests into infra others use. Earns trust across the org. You build standing with the whole team, not just leadership. Discreet. You handle sensitive context with care. What we offer Cloaked is a well-funded Series B startup based out of NYC. Although we are a distributed team, the NYC team operates with a hybrid model. We have two floors of our building, with two state of the art kitchens packed with drinks, snacks and everything else you need to get through the day. The Cloaked team has diverse interests and so we frequently embark on team outings and go out for socials! Compensation and Benefits We offer above market rate pay and equity based off of the market's best commercially available data. Your compensation will be a combination of salary, bonus and equity. For full-time US employees, we offer a comprehensive benefits package: medical, dental and vision with Cloaked covering the majority of employee premiums, company-paid basic life and a 401(k) with company match. We offer flexible work arrangements and the ability to work remotely as needed. Cloaked provides a home office stipend in addition to a new company laptop (and other tech depending on the role). Perks Competitive PTO: PTO, floating holidays and sick days — and we push people to actually use them. We see time off as a preventative burnout measure, not a balance to hoard. Parental Leave: Paid leave for all new parents — birth, adoption, or foster placement — because the people building privacy deserve time with their families. Monthly wellness & meals stipend: Used for any kind of physical, mental or emotional care you'd like to take for yourself, be it a gym membership, a meditation app, or time with a personal trainer — plus lunch and coffee during the workday. Professional Growth: Opportunities for career development and personal growth are provided to all employees who seek to further their knowledge and capabilities through an unlimited professional development fund. Additionally team members are encouraged to regularly attend conferences and industry events. We are really excited about having you join our mission-driven team and help us build the future of online privacy! #J-18808-Ljbffr Cloaked