Chief of Staff

Vitally — NYC (Hybrid, 2–3 days in office)

About the role

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.

What you'll own

Operating Cadence

You'll own the rhythm of how Vitally runs at the executive level. That means leadership meetings, all-hands, board prep, and the connective tissue between them — making sure the right conversations happen at the right time, with the right prep, and that decisions actually turn into action.

AI Adoption Across the Company

Every team at Vitally has workflows that AI should be making faster, cheaper, or better. Right now, no one owns finding them. That changes with this hire.

You'll go deep with each team — understanding how they work, where the friction is, and where AI can meaningfully move the needle. Some of what you find you'll solve directly, spinning up a working internal tool or agent yourself. The rest you'll route to our Operations team, which is expanding its AI tooling capacity, to build and deploy. Either way, you own the outcome — not just the discovery.

This is part researcher, part product manager, part builder. The thing we don't want is a deck full of recommendations that never ship.

Internal Tooling and Prototypes

The CEO is technical and prototypes a lot of internal tools using AI. You'll take half-formed ideas, sketches, and brainstorms and turn them into working internal apps and agents. You don't need to be a software engineer — but you do need to be genuinely fluent with modern AI tools and comfortable shipping working software with them.

Cross-functional Execution

Every company has projects that don't have a natural owner — initiatives that span functions, fall between teams, or need CEO sponsorship to land. Those become yours. You'll scope them, drive them, and close them out.

Internal communications

All-hands content, company-wide announcements, sensitive comms during transitions. You'll co-own the voice of the company internally, working closely with the CEO to make sure messages land clearly and humanely.

Culture presence

As a visible and trusted leader across the organization, you'll naturally become someone employees gravitate toward. We're looking for someone who is social, approachable, and adept at reading a room — someone who complements our People & HR function by being a steady, human presence for the team day-to-day.

What we're looking for:

Required

• Strong operator instincts. You like getting things done, you don't need a playbook, and you can take a vague problem and turn it into a clear plan with owners and deadlines.
• Genuine AI fluency. You actively use AI tools to build, automate, and prototype — not just for writing assistance. You can take an idea and ship a working agent or internal app with it. We don't care which tools; we care about output.
• Excellent written and verbal communication. You can write a clean all-hands update, draft a sensitive message, and run a productive meeting.
• Sound judgment under ambiguity. You'll see a lot of confidential information and weigh in on hard calls. You need a calibrated sense of what to escalate, what to handle, and what to leave alone.
• Socially capable. People should want to talk to you. You're warm, direct, and unflappable in the kinds of small awkward moments that come up at a 80-person company.
• NYC-based and able to be in our office 2–3 days per week.

Nice to have

• 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).

Compensation and Logistics

• Base salary: $175,000–$200,000, depending on experience.
• Reports directly to the CEO.
• Hybrid in NYC, 2–3 days per week in our office.
• Equity: We want every team member invested in the company’s success and are happy to be generous with equity.
• Benefits :
  • 100% of health/dental/vision insurance premiums covered by us.
  • 401k
  • Unlimited PTO with a minimum we require you to take off. Please relax and recharge!
  • Flexible work hours and work-from-home policy.
  • Yearly education stipend.

• Culture: We are committed to a productive and respectful work environment. Culturally, the team is extremely friendly, fun, hard-working, intelligent, and mature. That said, while we're young and scrappy as a team, we don't believe in building a startup cult. We like each other, we support each other, we're a focused team that busts our asses at work, and we enjoy hanging out from time to time-- but we enjoy having our own lives outside of Vitally.