Director of CEO Operations & Executive Affairs

Gesture•New York, NY

2d•Onsite

About The Position

Gesture is where technology meets humanity — a place where innovation, emotion, and impact collide. We’re a fast-growing tech company using AI, machine learning, and intelligent logistics to power a first-of-its-kind platform that connects people and brands through real-world, tangible experiences. From our mobile app to our B2B Reach360 platform, Gesture blends data, emotion, and automation to build the future of human connection — at scale. Inside our NYC headquarters, you’ll find an environment that moves with the pace and precision of Silicon Valley but with the heart of something far greater. We run on cutting-edge tools, creative experimentation, and raw ambition. Every project, every campaign, every moment you work on here matters — because it’s seen, felt, and experienced by real people around the world. At Gesture, you’ll work alongside some of the smartest, most driven operators, engineers, and creatives in the industry — people who think big, move fast, and care deeply about the work they do. This is a front-row seat to the future of connection. If you want to help build something that’s changing how the world interacts, welcome to Gesture. Gesture is a late-stage, venture-backed technology company in full hyper-scale mode. The CEO is operating across capital strategy, investor and board relationships, major partnerships, product vision, and market expansion simultaneously. At this pace and at this scale, the CEO needs one person who makes all of that possible without friction, without dropped threads, and without having to ask twice. This is that role. Director of CEO Operations & Executive Affairs is the person who runs the CEO's world so the CEO can run the company. You are the first line of defense, the last line of quality control, and the most trusted person in the executive office. You know what matters before you are told, you move before you are asked, and you operate with a level of discretion and judgment that most people never develop in an entire career. This is not a traditional executive assistant role. It is not a scheduling job dressed up with a title. The administrative function is real and it is owned completely, but it is one dimension of a role that also requires strategic thinking, exceptional communication, and the ability to represent the CEO with credibility across investors, board members, partners, and the internal leadership team. If you need to be told what to do next, this is the wrong role. If you see what needs to happen and make it happen, keep reading.

Requirements

You have supported a C-suite executive, founder, or CEO in a fast-moving, high-growth environment
You have managed complex, multi-stakeholder calendars and travel with zero margin for error
You have drafted and sent communications on behalf of a senior executive that required no revision
You have handled confidential HR, legal, and financial matters and maintained complete discretion
You have attended executive meetings, owned follow-through, and delivered without being chased
You operate proactively, not reactively. You see around corners
You have exceptional written and verbal communication skills across every register: formal, conversational, investor-facing, and internal
You are comfortable navigating ambiguity, urgency, and competing priorities simultaneously
You hold yourself to a standard that most people would find exhausting
You are onsite in NYC, full-time
You are willing to travel as required to support the CEO

Nice To Haves

Experience supporting a CEO or founder at a venture-backed technology company
Exposure to investor relations, board governance, or capital markets communications
Background in legal, finance, or HR that informs how you handle sensitive matters
Experience managing a CEO's public presence or external brand
Familiarity with fast-moving startup environments where the playbook changes weekly

Responsibilities

The CEO's calendar, schedule, and time, treated as the company's most valuable and non-renewable resource
All travel and logistics for the CEO, end-to-end, without gaps or surprises
Gatekeeper and correspondence management, ensuring the right people get access and the right communications get through
Board and investor prep, from materials to logistics to follow-through
Internal and external communications on behalf of the CEO, drafted and quality-controlled to the CEO's standard
Follow-through on every commitment, decision, and action item that comes out of the CEO's meetings and engagements
The CEO's presence in the world, protecting it, managing it, and elevating it at every touchpoint
Own and manage the CEO's calendar with strategic intent, not just logistical coordination
Prioritize, protect, and structure the CEO's time around the company's highest-value activities
Anticipate scheduling conflicts, preparation requirements, and time gaps before they become problems
Manage competing demands on the CEO's time with diplomacy, firmness, and good judgment
Ensure the CEO is never walking into a meeting unprepared or overextended
Own all CEO travel end-to-end: flights, accommodations, ground transportation, itineraries, and contingencies
Anticipate and resolve logistics issues before they surface
Manage travel changes, cancellations, and last-minute adjustments without disruption
Ensure the CEO arrives at every engagement on time, prepared, and ready to perform
Coordinate and prepare all board meeting logistics, materials, and follow-through
Support the CEO in preparing investor updates, decks, and correspondence
Manage investor and board member communications with professionalism and precision
Track board and investor commitments and ensure timely follow-through
Handle sensitive communications with the discretion and accuracy these relationships demand
Serve as the primary point of contact for inbound communications to the CEO
Filter, prioritize, and route correspondence with sound judgment
Draft, edit, and send communications on behalf of the CEO across internal and external audiences
Manage relationships with key external stakeholders: partners, vendors, investors, and board members
Protect the CEO's focus without creating friction or damaging relationships
Attend leadership meetings and own all follow-through: action items, decisions, and commitments
Prepare the CEO for internal engagements: briefings, all-hands, team reviews, and one-on-ones
Serve as a communication bridge between the CEO and the leadership team
Track cross-functional commitments made in the CEO's name and ensure accountability
Handle sensitive HR and legal communications with complete confidentiality
Support the CEO in coordinating with legal counsel, HR leadership, and external advisors
Manage confidential documentation, agreements, and correspondence with precision and discretion
Never allow sensitive information to move beyond its intended audience

Benefits

Full benefits: health, dental, vision, equity and stock options
Make a Gesture Day: Each employee receives the chance to earn credit to send a surprise gift to someone they admire — living the company mission firsthand.
Gesture Swag Pack: exclusive branded gear (hoodie, water bottle, or cap)
Beautiful HQ Experience: Modern New York office with creative work zones, media studio, and collaboration spaces.
Paid Team Lunches or Coffee Hours: Casual networking with leadership and cross-department peers.
Performance bonus tied to company revenue targets, OKR achievement, and individual contribution metrics
Equity participation commensurate with scope and tenure
Professional development budget

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