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 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 youll 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 its seen felt and experienced by real people around the Gesture youll 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 you want to help build something thats 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:

Were 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. Were building intelligence directly into the core of how campaigns are planned executed and measuredat scale.

At Gesture youre not joining a static MarTech company. Youre 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.

Most companies separate the person who runs operations from the person who runs the CEOs agenda. We dont believe in that split. This role exists because we need one person who can do both and who understands that those two mandates are inseparable at the pace we operate.

The Director of Business Operations & Executive Strategy is the connective tissue of the company. You sit at the intersection of strategy and execution translating the CEOs vision into an operating model that drives revenue scales the business and makes sure the right decisions get made owned and followed through on.

This is not a back-office role. Every function you touch has a revenue implication. Your job is to make sure the entire organization is pointed at growth and moving fast enough to capture it.

Lets be direct about the environment: this is not a place for corporate managers. It is not a place for people who manage up protect their lane or mistake activity for output. There are no layers to hide behind no slow approval chains and no tolerance for the kind of politics that makes big companies slow. If your instinct when things get hard is to call a meeting stop reading here. If your instinct is to fix it keep going.

WHAT THIS ROLE ACTUALLY IS

You will personally own:

• The companys 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 CEOs 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

Lets 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 companys 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 CEOs bandwidth. You expand it or youre not doing your job

When revenue is up and execution is clean you get credit. When the business misses and execution is the reason it falls on you.

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 whats 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 companys 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 CEOs Leverage

• Extend the CEOs 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 CEOs 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 companys 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. Youve 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 doesnt 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 CEOs 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 should not apply if:

• 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
• Youre looking for a polished corporate environment where someone else absorbs the pressure
• Youve 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

We are not looking for someone who manages things. We are looking for someone who runs things and drives growth while doing it. If you are the person in the room who sees what needs to happen before anyone else steps into the gap without being asked and holds execution standards high when everything around you is moving fast we want to hear from you.

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 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 builders 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 thats redefining how the world connects.

Join the MovementIf youre ready to lead by doing grow fast and make an impact that matters we want to hear from you.