Chief of Staff & Executive Assistant to CMO

The Opportunity

The Exclusive Collective brings together some of the world’s most distinguished luxury travel brands: Exclusive Resorts, Inspirato, onefinestay and Bespoke. We are seeking a Chief of Staff & Executive Assistant to partner with our Chief Marketing Officer and help lead the marketing organization behind each of them.

This is a fully marketing-focused role at the center of a multi-brand marketing organization. Beyond managing the CMO’s calendar, you will serve as her trusted partner and the operational engine of the department: owning the budgets, building the AI foundation the team works from and helping shape the strategic updates delivered to each brand’s President and CEO.

The role spans four areas: executive support for the CMO, marketing budget management across the Collective, the design and rollout of our marketing AI foundation, and strategic decks and updates for brand leadership. It is well suited to an organized operator, a strong writer and a systems thinker who is motivated to help define how a modern marketing team works.

What You'll Do

Strategic Decks & President Updates

• Partner with the Senior Director of Brand Strategy to compile regular marketing updates for each brand President, covering what we did, what it delivered and what comes next.

• Translate the CMO’s direction into executive, board and leadership presentations, gathering inputs from across the team, pressure-testing the numbers and shaping a clear narrative.

• Maintain a single source of truth for marketing performance and priorities.

• Prepare the CMO for leadership meetings with pre-reads, briefing materials and talking points, and follow through on decisions, owners and deadlines afterward.

Marketing Budget Management Across the Collective

• Own the consolidated marketing budget and shared-services tracker across all brands, including plan, committed spend, actuals and forecast.

• Reconcile spend across brand entities and systems, including Ramp, and manage the allocation of shared costs such as agency fees between brands.

• Manage invoices, purchase orders and new vendor setup, and serve as Marketing’s day-to-day partner to Finance.

• Deliver a monthly budget-versus-actuals view with clear recommendations, identifying overspend or underused budget early.

• Support annual and mid-year budget planning by brand and by channel.

AI Foundation

• Lead the setup and ongoing management of the marketing team’s AI foundation, including shared workspaces, reusable workflows and agents, brand voice profiles, and templates for reporting, budgeting and content.

• Define how Marketing uses AI, establishing the structure, standards and guardrails for approved tools, data privacy, brand separation and quality review before anything is published.

• Drive adoption across the team through training, playbooks and office hours, and measure impact by time saved and quality of output rather than usage alone.

• Partner with Engineering, IT and vendors where deeper integrations with our marketing platforms are required.

• Continually identify opportunities for AI to reduce manual work across the CMO’s office and the wider team, beginning with your own.

Executive Support for the CMO

• Manage the CMO’s calendar strategically, balancing internal priorities, external relationships, travel and personal commitments while protecting time for the highest-value work.

• Coordinate meetings across brand leadership, the marketing team, agencies, partners and external stakeholders.

• Arrange domestic and international travel, including flights, accommodations, ground transportation and itineraries.

• Track key decisions, action items, deadlines and follow-ups, including both the CMO’s commitments and those owed to her.

• Draft and coordinate executive correspondence with a strong command of voice, context and audience.

• Manage expenses and executive-office administration.

What Success Looks Like in Year One

• Each President receives a clear, timely marketing update every month, without the CMO needing to follow up.

• Marketing has a single, reliable budget view across the Collective, reconciled monthly.

• The marketing AI foundation is live, documented and adopted across the team, with measurable time savings.

• The CMO has significantly more time to devote to strategy, brand and team leadership.

Who You Are

You think two or three steps ahead. Rather than waiting to be told what needs to happen, you anticipate it and build the systems that keep it from becoming an issue again.

You combine polish with rigor: at ease with senior executives, confident with a spreadsheet and skilled at turning complex inputs into a clear, compelling story. You are equally willing to roll up your sleeves when a problem needs solving.

You see AI not as a novelty but as a meaningful way to change how a team works. You enjoy building something new and want to play a central role in how a growing marketing organization operates.

What You'll Bring

• 6+ years of experience as a chief of staff or executive assistant, or in marketing operations, strategy or a similar role supporting senior executives, ideally within a fast-paced, high-touch organization in luxury, hospitality, travel or membership.

• Strong financial acumen, with experience managing budgets, tracking spend and reconciling actuals, and advanced proficiency in Excel or Google Sheets.

• Excellent writing and presentation skills, with a track record of building executive-level decks and updates.

• Hands-on experience with AI tools such as Claude or ChatGPT beyond casual use, including building workflows, templates or automations, and a systems-oriented mindset.

• Exceptional calendar management, prioritization and organizational skills.

• Sound judgment and the ability to handle highly confidential information with discretion.

• Meticulous attention to detail without losing sight of the broader picture.

• Confidence working with executives, brand Presidents, agencies and Finance.

• Composure, flexibility and a solutions-oriented approach when priorities change quickly.

• Strong proficiency with Microsoft Office, Google Workspace and modern productivity and collaboration tools.

• Willingness to work outside traditional business hours on occasion, as executive schedules, travel or deadlines require.

• Based in or within a reasonable commute of New York City, with the ability to transition to a hybrid working model.