Director of CEO Operations & Executive Affairs, Gesture

• 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
• 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

Desirable

• Reports To: Chief Executive Officer (CEO)
• 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.'
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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

• 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