Chief of Staff

Breckenridge Grand Vacations•Breckenridge, CO

2d•$149,760 - $187,200•Onsite

About The Position

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. Working directly under the Chief Operating Officer and in close partnership with the Chief Revenue & Strategy Officer, you will drive performance across our fractional real estate revenue divisions, Sales, Marketing, and Analytics, while aligning with Finance, Hospitality, and Development to ensure financial discipline and operational excellence. You will be the connective tissue between our executive vision and cross-functional outcomes. This role is for a hands-on leader who thrives on converting strategic memos into actionable workplans, holding projects accountable to milestones, and freeing executive bandwidth for the highest-value work. You will manage our most sensitive strategic initiatives, from go-to-market launches and pricing integrity to new market expansion and innovation pipelines, all while operating with the discretion and judgment that BGV's leadership trusts at the highest level. If you are a structured thinker with a bias to action, comfortable influencing without authority in a fast-paced, multi-market environment, and ready to own outcomes, not just activity, we’d love to meet you.

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

Nice To Haves

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

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.
Coordinate 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.
Support performance management cadence, including PDPs and review preparation for the COO and direct reports.
Lead discrete projects assigned by the COO and CRSO, including compliance work, organizational design, vendor selection, and cross-functional process improvement.
Support preparation of investor reporting, lender reporting, and board materials in partnership with the COO, CFO, CRSO, and CHO.

Benefits

Health, vision, and dental insurance plans
Company-paid life insurance coverage
Voluntary Life and Accidental Death/Dismemberment Insurance
HSA and FSA-Dependent Care Accounts
Retirement plan
Generous paid time off (PTO) and sick leave to support work-life balance
Volunteer Time Off - Paid opportunities to give back to Summit County
Bereavement leave
Biannual bonuses
Tuition Reimbursement Program
Employee Wellness programs to support physical and mental health
Lifestyle perks: Ski/Rec center pass loan programs, lodging and gear discounts, sporting/concert event tickets, pet insurance partner discounts and access to Summit Medallions: Occasional-use transferable passes for access to 6 premier resorts (A-Basin to Vail) via owners’ program