Technical Chief of Staff
for section headings. We need sections: About the role (we have). Responsibilities (we have "What you'll do?" list). Requirements (maybe combine skills and experiences? Could be "Skills and experiences will help you" as Requirements). Qualifications maybe not separate; we could omit if no distinct content. Skills maybe same as Requirements? The instruction: prefer few substantive sections over many thin ones. We could combine Skills and Requirements into one section? But they ask to use headings for those categories if content exists. We have content for Responsibilities, Skills/Experience (maybe as Requirements), Benefits, Pay. Also maybe "About the role" is needed. Schedule? Not mentioned specifically except hybrid model, remote flexibility. Could infer schedule: flexible work arrangements, remote as needed. That's schedule info. So we can include Schedule section with that content. Benefits: we have medical, dental, vision, life, 401k, home office stipend, laptop, PTO, parental leave, wellness stipend, professional growth fund. Also mention hybrid model, offices, kitchens, team outings. Those are perks/benefits. Pay: compensation range $200K-$220K, above market rate pay and equity, salary bonus equity. Thus we will output sections: About the role, Responsibilities, Requirements (or Skills), Benefits, Pay, Schedule. We must not include empty sections. Let's craft HTML. We need to preserve all substantive information; not invent or summarize away detail. Must not omit details like "600k+ paying members", etc. That's in intro but not part of sections? The intro is before About The Role. Should we include that? The instruction: "Preserve ALL substantive information". The intro is substantive but not under a heading. We could include it as a
before the first heading? The instruction says output only HTML fragment, we can include paragraphs before headings. It didn't forbid that. So we can include an introductory paragraph summarizing the company description. Then headings. We must not repeat job title. No job title given explicitly; it's "Technical Chief of Staff". We should not repeat that as heading. Let's extract details: Intro: "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." That's all before About The Role. Now About The Role paragraph: "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!" Now Responsibilities: "What you'll do?" list: - 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. Now Skills/Experiences: "What skills and experiences will help you?" list: - 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. Now "What we like?" list (values) maybe not needed but could be included under Skills? But we can omit as not a required section. Now Benefits/Compensation: "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'd 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! Compensation Range: $200K - $220K" We need to separate Benefits and Pay sections. Pay: compensation range, above market rate pay and equity, salary bonus equity. Benefits: medical/dental/vision, life, 401k match, flexible work, remote, home office stipend, laptop, PTO, parental leave, wellness stipend, professional growth fund, office perks (kitchens, team outings, hybrid model, NYC offices). Schedule: flexible work arrangements, ability to work remotely as needed, hybrid model. We could put schedule info under Benefits or separate Schedule. Since they ask to include Schedule section only if posting actually states them. It does mention flexible work arrangements and ability to work remotely as needed, hybrid model. So we can include Schedule. Now craft HTML. We'll start with an introductory
containing the company description. Then
About the role
...
ThenResponsibilities
- ...
Requirements
- ...
Benefits
- ...
Pay
...
ThenSchedule
...
We must not include empty sections. Let's write content precisely. Intro paragraph: combine the first paragraph(s) before About The Role. Intro: "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." Now About the role paragraph as given. Now Responsibilities list items exactly as bullet points. Now Requirements list: include the six items plus bonus. We'll list each as