Chief of Staff

About the role

At Breckenridge Grand Vacations, we create Grand Vacations by Sharing Smiles with every Owner, Guest, and coworker. As our Chief of Staff, you will be the force multiplier for our C-Suite, operating at the intersection of strategy and execution to turn leadership decisions into operating reality.

Responsibilities

• Manage the COO's and CRSO's strategic agenda, project portfolio, and operating cadence to improve executive efficiency.
• Serve as a first-line filter for escalations, determining what warrants C-suite attention and proactively escalating when needed.
• Prepare materials, briefings, and pre-reads for executive team, investor, and board meetings.
• Track commitments and decisions across leadership meetings and drive follow-through to closure.
• Own day-to-day execution of priority cross-divisional initiatives, including go-to-market strategies, sales launch coordination, pricing integrity, inventory revenue management, and analytics support.
• Partner with the CRSO and EVP Marketing to evolve the timeshare marketing playbook for multi-market expansion.
• Partner with the CRSO and EVP Sales to drive sales execution performance, including close rates, VPG/ASP growth, and sales line productivity.
• Cook with the CHO on resort operations, property management, and owner/guest experience to align with profitability goals.
• Drive integration of whole ownership sales and marketing with timeshare sales and marketing operations alongside the COO and CDO.
• Build and shepherd an innovation pipeline of revenue and operating concepts (AI, new product configurations, channel tests) from idea to pilot to commercial deployment.
• Partner with the CRSO, EVP Marketing, and EVP Sales to strengthen the owner upgrade flywheel (loyalty, trade-ins, inventory implications).
• Maintain initiative dashboards, milestones, and risk logs; escalate blockers quickly and propose solutions.
• Convert strategic memos and OKRs into actionable workplans with named owners and target dates.
• Synthesize information from divisional leaders into clear options and recommendations for the C-suite.
• Draft executive-level memos, board materials, and stakeholder communications in the COO's voice.
• Build and maintain decision logs, performance reviews, and structured updates for executive review.
• Lead discrete projects assigned by the COO and CRSO, including compliance work, organizational design, vendor selection, and cross-functional process improvement.
• Support performance management cadence, including PDPs and review preparation for the COO and direct reports.
• Support preparation of investor reporting, lender reporting, and board materials in partnership with the COO, CFO, CRSO, and CHO.

Requirements

• Bachelor's degree, or equivalent professional experience
• Minimum 7 years of progressive experience in marketing, sales, operations, strategy, consulting, corporate development, or a prior Chief of Staff role
• Demonstrated ability to manage complex, cross-functional initiatives to completion
• Advanced written and verbal communication skills, with the ability to draft executive-level content quickly and accurately
• Strong analytical capability; fluency with Excel, PowerPoint, and basic data tools
• Track record of operating with discretion and confidentiality in executive settings
• Ability to work in-office in Breckenridge, CO

Preferred Qualifications

• MBA or graduate degree in business, finance, hospitality, or a related field
• Experience in hospitality, real estate development, timeshare, rental program operations, food & beverage, or vacation ownership
• Demonstrated commitment to building financial acumen, including proactive pursuit of continuing education in corporate finance, accounting, or capital markets relevant to a complex, multi-entity operating environment
• Familiarity with private equity-backed, family-owned, or founder-led business environments
• Prior exposure to investor reporting, board governance, or capital markets transactions
• Working knowledge of the timeshare regulatory framework or related compliance environments