Director of Business Operations & Executive Strategy

Department: Operations Management Function: Business Operations & Executive Strategy Reports To: Chief Executive Officer (CEO) Direct Reports: Cross‑functional team leads; scope scales with organizational growth Location: Onsite, NYC (Full‑Time) Travel: As required (est. 20‑30%) Employment: 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. We are past the experimental stage. The product works, the market is real, and the revenue target is aggressive. What we need now is execution at a pace and intensity that most corporate environments are simply not built for. WHAT THIS ROLE ACTUALLY IS You will personally own: The company’s operating rhythm: OKRs, KPIs, quarterly planning cycles, and weekly execution cadence, all anchored to revenue outcomes Cross‑functional project delivery: launches, expansions, sales enablement, and revenue‑driving operational improvements Organizational accountability for all revenue‑generating departments including Sales, B2B, Partnerships, and Consumer Mobile App, ensuring they have what they need to close, convert, and scale Metrics, reporting, and operational visibility that give leadership real‑time command of pipeline, revenue, and growth performance across all business lines The CEO’s most important strategic and revenue‑critical projects, from concept through execution, without hand‑holding Process and tooling that removes friction from the sales motion and accelerates time‑to‑revenue You will run point on execution. You will not 'support' it. WHAT THIS ROLE IS NOT Let’s be clear: This is not a 'check in with teams and take notes' role This is not a project coordinator position This is not a 'build decks and give status updates' job This is not a role for people who avoid conflict, accountability, or deadlines This is not a role for operators who need a large team or perfect conditions to be effective This role crosses slightly into that of a Chief of Staff, doing what is necessary to free up the CEO to focus on capital strategy, key investor and board relationships, major partnerships, and the product and market bets that determine the company’s trajectory, but make no mistake, the mandate here is significantly broader, the ownership significantly deeper, and the revenue accountability real If you have never directly owned outcomes with real consequences, including revenue consequences, this will be painful WHAT YOU WILL BE HELD ACCOUNTABLE FOR You own: Revenue execution rhythm, pipeline visibility, sales cadence accountability, and cross‑functional alignment to close across all business lines Company operating cadence, weekly and monthly reviews, without exception Cross‑functional delivery and launch reliability across every function, measured by revenue impact Removal of every internal barrier slowing down Sales, B2B, Partnerships, and the Consumer Mobile App from hitting number Operational throughput and cycle time: idea to shipped, deal to closed, issue to resolved Strategic initiative performance: on‑time, on‑budget, tied to growth outcomes Quality control: fewer errors, fewer escalations, fewer fires that cost revenue Organizational clarity: who owns what, by when, and what 'done' actually means The CEO’s bandwidth. You expand it or you're not doing your job WHAT YOU WILL OWN I. Revenue Operations & Sales Accountability Own the cross‑functional operating model that supports and accelerates revenue across all business lines, ensuring Sales, B2B, Partnerships, and the Consumer Mobile App are unblocked, resourced, and accountable Drive pipeline visibility across the organization: every leader knows where deals stand, what's at risk, and what needs to move Identify and eliminate internal barriers killing sales velocity and consumer growth, whether they live in process, product, ops, or people Hold all revenue‑generating teams including B2B, Sales, Partnerships, and Consumer Mobile App to their commitments in the weekly operating cadence; surface gaps early and drive corrective action fast Partner with Sales, B2B, and Consumer Mobile App leadership to translate revenue targets into operational plans with clear owners and timelines Evaluate and implement tooling, workflow, and process improvements that reduce friction in the sales motion and consumer growth engine II. The Operating Engine Design and own the company’s operating rhythm: OKRs, KPIs, quarterly planning cycles, and weekly leadership cadence Drive cross‑functional execution, translating strategy into 90‑day sprints with clear owners, milestones, and accountability checkpoints Build the dashboards, reporting infrastructure, and review processes that give leadership real‑time visibility into business health Identify operational drag before it becomes organizational failure. Fix it before anyone notices Lead monthly and quarterly business reviews; surface risks early and drive corrective action with urgency III. The CEO's Leverage Extend the CEO's bandwidth across strategic priorities, key relationships, and high‑stakes follow‑through Prepare the CEO for every critical engagement: board meetings, investor updates, all‑hands, and external partnerships Own the CEO's most important special projects, from concept through execution, without hand‑holding Represent the CEO in leadership meetings and with external stakeholders when delegated. Show up fully Draft and quality‑control high‑stakes communications: internal memos, board materials, investor decks, and partner correspondence Hold confidences, exercise discretion, and never let sensitive information become organizational noise IV. Organizational Effectiveness Partner with HR and functional leaders to build a culture where accountability, especially revenue accountability, is the norm, not the exception Drive headcount planning, team structure decisions, and role prioritization with a clear lens on revenue impact across both B2B and Consumer Identify gaps in organizational capability that are costing the business growth and close them fast Build leadership bench strength by identifying and investing in high‑potential operators across the business V. Financial Discipline Partner with Finance to build and defend the operating budget; connect every dollar of spend to revenue outcome or strategic necessity Own financial reporting for operational functions; hold OPEX efficiency and ROI accountability across the business Lead resource allocation decisions with a clear bias toward revenue‑generating and revenue‑enabling functions across all business lines Bring a rigorous cost‑benefit lens to build‑buy/partner decisions VI. Strategic Planning & Market Intelligence Lead the annual strategic planning process end‑to‑end, with revenue growth across B2B and Consumer as the north star Synthesize competitive intelligence, market dynamics, and internal performance data into actionable growth recommendations Evaluate new business opportunities, partnerships, and market expansion with a defined revenue thesis and risk framework Translate long‑range growth vision into near‑term execution plans that teams can actually run VII. Legal, Compliance & Risk Coordinate with legal counsel on contracts, vendor agreements, regulatory compliance, and corporate governance Maintain the company's risk register; surface legal, operational, and reputational risks to the CEO before they surface themselves Ensure company‑wide adherence to policies, regulatory requirements, and contractual obligations WHAT SUCCESS LOOKS LIKE In 30 days, you have command of the business: revenue, operations, people, and priorities. You've identified where execution is breaking down and have a plan to fix it. In 60 days, the major bottlenecks are gone, the operating cadence is running cleanly, and the CEO is getting a tight, reliable briefing every week. In 90 days, execution is predictable. Revenue teams are moving faster. Launches are reliable. The business has less noise and more output. This role has real influence, real impact, and real responsibility. It also has nowhere to hide. WHAT YOU MUST HAVE (NON-NEGOTIABLE) Do not apply unless you can honestly say yes to all of the following: You have personally owned cross‑functional execution in a fast‑moving, revenue‑driven company You have held operational teams accountable to revenue outcomes, not just activity metrics You have built operating cadences that produce real delivery and real revenue results, not just meetings You understand sales motion, pipeline dynamics, and what it takes operationally to help a sales team close You are excellent at forcing clarity: priorities, owners, timelines, and revenue outcomes You know how to implement process without slowing the business down You can work directly with Sales, B2B, Consumer Mobile App, Engineering, Product, Finance, HR, and Legal in the same week You have strong judgment under ambiguity and can make decisions quickly You are comfortable with direct accountability and high standards, including when the number is missed You are financially fluent: P&L management, budget construction, unit economics, revenue modeling You write and communicate with precision: memos, decks, and difficult conversations alike You are onsite in NYC, full‑time You are willing to travel as needed BONUS POINTS MBA from a top‑tier program or equivalent analytical rigor demonstrated through career trajectory Experience in high‑growth technology, SaaS, marketplace, or venture‑backed environment Prior P&L ownership or general manager experience with direct revenue responsibility Background in revenue operations, sales operations, or go‑to‑market strategy JD or legal background: contracts, governance, and risk management are part of this role Comfortable operating lean, resourceful and inventive when the playbook doesn't exist yet HOW YOU OPERATE Structural Clarity: You break complexity into structure, not the other way around Revenue Orientation: Every operational decision you make has a growth implication across both B2B and Consumer. You never lose sight of that Bias for Action: You decide with incomplete information and course‑correct fast Accountability: You hold yourself and others to high standards, especially when revenue is on the line Ego‑Free: Your success is measured by the CEO's output and company results, not your own visibility Range: Board deck in the morning, sales pipeline review at noon, consumer growth metrics by 3pm. You navigate all of it Metrics‑First: Revenue metrics are your first language. Everything else follows WHO SHOULD NOT APPLY You prefer coordination over ownership You avoid conflict, accountability, or hard conversations, especially with revenue teams You need perfect information to act You rely on "process" as a substitute for execution You have never been directly tied to a revenue number and felt it You want remote work or low‑touch responsibility You're looking for a polished corporate environment where someone else absorbs the pressure You've never been the person a CEO actually depended on 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 OTHER GESTURE BENEFITS AND PERKS 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. 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.vipto 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. #J-18808-Ljbffr