Operations Admin to CEO & Executive Affairs

Function: Executive Office & CEO OperationsReports To: Chief Executive Officer (CEO)Location: Onsite, NYC (Full-Time)Travel: As required; mirrors CEO travel scheduleEmployment: Full-Time | ExemptAbout GestureGesture 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 HEADEDGesture Is Investing Aggressively In AI-driven Intelligence To Power The Next Generation Of Marketing And Commerce Using a Gift-centric Approach. Our Roadmap Focuses OnWe’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 OPPORTUNITYGesture 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 IsYou will personally own:The CEO's calendar, schedule, and time, treated as the company's most valuable and non-renewable resourceAll travel and logistics for the CEO, end-to-end, without gaps or surprisesGatekeeper and correspondence management, ensuring the right people get access and the right communications get throughBoard and investor prep, from materials to logistics to follow-throughInternal and external communications on behalf of the CEO, drafted and quality-controlled to the CEO's standardFollow-through on every commitment, decision, and action item that comes out of the CEO's meetings and engagementsThe CEO's presence in the world, protecting it, managing it, and elevating it at every touchpointYou are not support staff. You are the operating layer that makes the CEO effective.What This Role Is NotLet's be clear:This is not a "manage the calendar and book travel" roleThis is not a receptionist, office manager, or administrative coordinator positionThis is not a role for people who need explicit direction for every taskThis is not a role for people who are uncomfortable with ambiguity, urgency, or confidentialityThis is not a role for people who treat discretion as optionalThis is not a role where you clock in, complete tasks, and clock outIf 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 adjustmentYou OwnWHAT YOU WILL BE HELD ACCOUNTABLE FORThe CEO's time. Nothing gets on the calendar that should not be there. Nothing falls off that should not be missedZero dropped threads. Every follow-through item from every meeting, call, and commitment is tracked and closedBoard and investor materials that are accurate, polished, and delivered on time, every timeCommunications that go out under the CEO's name that are on-brand, precise, and appropriate for the audienceA gatekeeper function that protects the CEO's focus without damaging relationshipsConfidential matters that stay confidential, alwaysA travel and logistics operation that runs seamlessly regardless of complexity or last-minute changesThe CEO's confidence that the executive office is running at the highest possible standardWhen 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 OwnI. CEO Calendar & Time ManagementOwn and manage the CEO's calendar with strategic intent, not just logistical coordinationPrioritize, protect, and structure the CEO's time around the company's highest-value activitiesAnticipate scheduling conflicts, preparation requirements, and time gaps before they become problemsManage competing demands on the CEO's time with diplomacy, firmness, and good judgmentEnsure the CEO is never walking into a meeting unprepared or overextendedII. Travel & LogisticsOwn all CEO travel end-to-end: flights, accommodations, ground transportation, itineraries, and contingenciesAnticipate and resolve logistics issues before they surfaceManage travel changes, cancellations, and last-minute adjustments without disruptionEnsure the CEO arrives at every engagement on time, prepared, and ready to performIII. Board & Investor CommunicationsCoordinate and prepare all board meeting logistics, materials, and follow-throughSupport the CEO in preparing investor updates, decks, and correspondenceManage investor and board member communications with professionalism and precisionTrack board and investor commitments and ensure timely follow-throughHandle sensitive communications with the discretion and accuracy these relationships demandIV. Gatekeeper & Correspondence ManagementServe as the primary point of contact for inbound communications to the CEOFilter, prioritize, and route correspondence with sound judgmentDraft, edit, and send communications on behalf of the CEO across internal and external audiencesManage relationships with key external stakeholders: partners, vendors, investors, and board membersProtect the CEO's focus without creating friction or damaging relationshipsV. Internal Leadership Team SupportAttend leadership meetings and own all follow-through: action items, decisions, and commitmentsPrepare the CEO for internal engagements: briefings, all-hands, team reviews, and one-on-onesServe as a communication bridge between the CEO and the leadership teamTrack cross-functional commitments made in the CEO's name and ensure accountabilityVI. Confidential HR & Legal MattersHandle sensitive HR and legal communications with complete confidentialitySupport the CEO in coordinating with legal counsel, HR leadership, and external advisorsManage confidential documentation, agreements, and correspondence with precision and discretionNever allow sensitive information to move beyond its intended audienceWhat Success Looks LikeIn 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 environmentYou have managed complex, multi-stakeholder calendars and travel with zero margin for errorYou have drafted and sent communications on behalf of a senior executive that required no revisionYou have handled confidential HR, legal, and financial matters and maintained complete discretionYou have attended executive meetings, owned follow-through, and delivered without being chasedYou operate proactively, not reactively. You see around cornersYou have exceptional written and verbal communication skills across every register: formal, conversational, investor-facing, and internalYou are comfortable navigating ambiguity, urgency, and competing priorities simultaneouslyYou hold yourself to a standard that most people would find exhaustingYou are onsite in NYC, full-timeYou are willing to travel as required to support the CEOBONUS POINTSExperience supporting a CEO or founder at a venture-backed technology companyExposure to investor relations, board governance, or capital markets communicationsBackground in legal, finance, or HR that informs how you handle sensitive mattersExperience managing a CEO's public presence or external brandFamiliarity with fast-moving startup environments where the playbook changes weeklyHow You OperateAnticipation: You solve problems that have not happened yet. Reactivity is a last resortDiscretion: You are trusted with information that most people in the company will never see. You treat that trust as sacredPrecision: 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 onJudgment: You make decisions independently and correctly, without waiting for instructionOwnership: You do not hand things off and hope for the best. You own outcomes from start to finishComposure: The higher the pressure, the more stable you become. The CEO depends on your calmWho Should Not ApplyYou should not apply if:You need explicit direction for every taskYou treat confidentiality as situationalYou are uncomfortable being the person who knows everything but says very littleYou prefer predictable, low-urgency environmentsYou want remote work or flexible hours that do not flex around the CEO's scheduleYou have never been the person a senior executive trusted completelyYou confuse being busy with being effectiveCompensationBase salary benchmarked competitively for a senior director-level executive mandatePerformance bonus tied to company revenue targets, OKR achievement, and individual contribution metricsEquity participation commensurate with scope and tenureProfessional development budgetWe 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 PerksFull 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 followingA 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 AppWe 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.