Function: Executive Office & CEO Operations
Reports To: Chief Executive Officer (CEO)Location: Onsite, NYC (Full-Time)Travel: As required; mirrors CEO travel scheduleEmployment: Full-Time | Exempt
ABOUT GESTURE
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.
WHERE WE ARE HEADED
Gesture is investing aggressively in AI-driven intelligence to power the next generation of marketing and commerce using a gift-centric approach. Our roadmap focuses on:We’re building intelligence that anticipates, adapts, and compounds, predicting intent, optimizing campaigns in real time, and delivering deeply personalized experiences driven by real-world behavior, all through systems that continuously learn and improve with every interaction.This is not surface-level automation. We’re building intelligence directly into the core of how campaigns are planned, executed, and measured—at scale.At Gesture, you’re not joining a static MarTech company.
You’re joining a team building the infrastructure for how brands will compete in a post-digital-fatigue world.
THE OPPORTUNITY
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.'
WHAT THIS ROLE ACTUALLY IS
You will personally own:
- 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
You are not support staff. You are the operating layer that makes the CEO effective.
WHAT THIS ROLE IS NOT
Let's be clear:
- This is not a "manage the calendar and book travel" role
- This is not a receptionist, office manager, or administrative coordinator position
- This is not a role for people who need explicit direction for every task
- This is not a role for people who are uncomfortable with ambiguity, urgency, or confidentiality
- This is not a role for people who treat discretion as optional
- This is not a role where you clock in, complete tasks, and clock out
- If you have never operated in a fast-moving, high-stakes environment where your judgment directly impacted a senior executive's effectiveness, this will be a difficult adjustment
WHAT YOU WILL BE HELD ACCOUNTABLE FOR
You own:
- The CEO's time. Nothing gets on the calendar that should not be there. Nothing falls off that should not be missed
- Zero dropped threads. Every follow-through item from every meeting, call, and commitment is tracked and closed
- Board and investor materials that are accurate, polished, and delivered on time, every time
- Communications that go out under the CEO's name that are on-brand, precise, and appropriate for the audience
- A gatekeeper function that protects the CEO's focus without damaging relationships
- Confidential matters that stay confidential, always
- A travel and logistics operation that runs seamlessly regardless of complexity or last-minute changes
- The CEO's confidence that the executive office is running at the highest possible standard
When the CEO is prepared, protected, and operating at full capacity, you are doing your job. When something slips, it falls on you.
WHAT YOU WILL OWN
I. CEO Calendar & Time Management
- 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
II. Travel & Logistics
- 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
III. Board & Investor Communications
- 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
IV. Gatekeeper & Correspondence Management
- 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
V. Internal Leadership Team Support
- 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
VI. Confidential HR & Legal Matters
- 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
WHAT SUCCESS LOOKS LIKE
In 30 days, the CEO's calendar is under control, the correspondence backlog is cleared, and the operating rhythm of the executive office is running cleanly.In 60 days, board and investor communications are organized and proactive, travel is seamless, and the CEO has measurably more time and mental bandwidth for the highest-value activities.In 90 days, the CEO has full confidence that the executive office operates at the highest standard with or without direct instruction. Nothing slips. Nothing surprises.
Everything is handled.This role has real influence, real access, and real responsibility. It also requires an uncompromising standard of excellence every single day.
WHAT YOU MUST HAVE (NON-NEGOTIABLE)
Do not apply unless you can honestly say yes to all of the following:
- 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
BONUS POINTS
- 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
HOW YOU OPERATE
- Anticipation: You solve problems that have not happened yet. Reactivity is a last resort
- Discretion: You are trusted with information that most people in the company will never see. You treat that trust as sacred
- Precision: Your work product is right the first time. Drafts, materials, and communications go out at a standard the CEO would be proud to put their name on
- Judgment: You make decisions independently and correctly, without waiting for instruction
- Ownership: You do not hand things off and hope for the best. You own outcomes from start to finish
- Composure: The higher the pressure, the more stable you become. The CEO depends on your calm
WHO SHOULD NOT APPLY
You should not apply if:
- You need explicit direction for every task
- You treat confidentiality as situational
- You are uncomfortable being the person who knows everything but says very little
- You prefer predictable, low-urgency environments
- You want remote work or flexible hours that do not flex around the CEO's schedule
- You have never been the person a senior executive trusted completely
- You confuse being busy with being effective
COMPENSATION
- Base salary benchmarked competitively for a senior director-level executive mandate
- Performance bonus tied to company revenue targets, OKR achievement, and individual contribution metrics
- Equity participation commensurate with scope and tenure
- Professional development budget
We are not looking for someone who manages a calendar. We are looking for someone who manages the conditions that allow a CEO to operate at the highest level. If you are the person who anticipates, executes, protects, and delivers without being asked, we want to hear from you.
OTHER GESTURE BENEFITS AND PERKS
Full benefits: health, dental, vision, equity and stock optionsMake 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.
Application Process - Interested candidates should submit the following
A resume outlining relevant experience.
A brief cover letter highlighting your key skills, achievements, and what excites you about this opportunity.
Any project work, portfolio samples, or coursework that demonstrate your passion and abilities.
Download The Gesture App
We strongly encourage all applicants to download the Gesture app and explore our platform firsthand. You can also visit gesture.vip
to learn more about our mission, technology, and culture.
Gesture is committed to maintaining fair, transparent, and performance-driven compensation practices.
Depending on the role, total compensation may include
commissions, bonuses, or
other performance-based incentives.
Final compensation packages are determined by factors such as years of experience, skill set, certifications, and location. Additional components may include
equity, annual performance rewards, and other incentive programs tied to company and individual results.At Gesture, we operate with a KPI-driven, pacesetting culture — one that rewards sharp, motivated, high-performing individuals who take initiative and execute with excellence.
The ideal candidate will thrive in a startup environment, embodying curiosity, grit, and a builder’s mindset. This is a ground-floor opportunity to grow alongside one of the most exciting and innovative companies redefining connection through technology.Apply today to join Gesture and be part of the team that’s redefining how the world connects.Join the Movement
If you’re ready to lead by doing, grow fast, and make an impact that matters, we want to hear from you.
