Chief of Staff

Vitally•Brooklyn, NY

2d•Hybrid

About The Position

Vitally is entering a pivotal stretch — sharpening our AI strategy, reorganizing the company around AI, and scaling the operating discipline that gets us to the next level. We're hiring our first Chief of Staff to work directly with the CEO. This is a high-trust, high-leverage role for someone who wants to operate at the center of a fast-moving startup — owning the company's operating cadence, driving cross-functional initiatives, and turning ideas into shipped outcomes. You'll partner closely with the CEO and the SVP of Revenue, with regular exposure to the full leadership team. The role doesn't have direct reports, and you won't be running a function — you'll be making the company run better.

Requirements

Strong operator instincts; ability to take a vague problem and turn it into a clear plan with owners and deadlines.
Genuine AI fluency; actively use AI tools to build, automate, and prototype, with a focus on output.
Excellent written and verbal communication skills.
Sound judgment under ambiguity; ability to weigh in on hard calls and know what to escalate.
Socially capable, warm, direct, and unflappable.
NYC-based and able to be in the office 2–3 days per week.

Nice To Haves

Prior CoS experience at a startup, especially Series B or later stage SaaS.
Background in management consulting, founding a company, or operations/strategy at a fast-growing startup.
Experience driving an AI transformation or major operational change at a previous company.
Comfort with modern AI development tools (Claude, Claude Code, Cursor, similar).

Responsibilities

Own the rhythm of how Vitally runs at the executive level, including leadership meetings, all-hands, and board prep, ensuring decisions turn into action.
Drive AI adoption across the company by identifying workflows that AI can improve, prototyping solutions, and collaborating with the Operations team.
Turn the CEO's half-formed ideas, sketches, and brainstorms into working internal apps and agents using AI tools.
Scope, drive, and close cross-functional projects that don't have a natural owner.
Co-own the internal voice of the company, working with the CEO on all-hands content, company-wide announcements, and sensitive communications.
Act as a visible and trusted leader, being approachable and a steady, human presence for the team.