Chief Commercial Officer

COMPANY OVERVIEW:

Create your ideal career with us at Juniper Holiday + Home

With a sincere passion for unreasonable hospitality, entrepreneurship, and real estate, we are spearheading a movement towards a more vibrant and inclusive future in the hospitality industry. Juniper Holiday + Home oversees a portfolio of properties in sought-after locations across Southwest Michigan and beyond.

Our mission: To make luxury vacation rentals and unparalleled service accessible to everyone.

Our motto: Live well. Travel well.

Our Commitment: Luxury is more than a standard—it's a declaration of our dedication to excellence.

Our commitment extends beyond our breathtaking designs and décor; it's about providing a new level of hospitality. With a focus on caring and attentive services, we ensure every moment with us is as enriching, relaxing, and carefree as possible.

Our Approach: We approach every day with innovation, drive, and dedication to providing unmatched service to our guests and homeowners. Together as a team, we’re proving that a centered and grounded business strategy is not only possible but necessary to achieving success.

Your Career with Juniper Holiday + Home: Take the next step in your career, where your passion for hospitality, entrepreneurship, and real estate can flourish. With us, you'll be at the forefront of an industry revolution, championing a new era of luxury, service, and fulfillment.

Join us as we continue to build a place where vacation rental experiences aren’t just about offering stays but about creating spaces for stories worth telling.

JOB DESCRIPTION SUMMARY

As Chief Commercial Officer, you’ll be the right hand to the CEO and the operational heartbeat of the company. You’ll be responsible for turning vision into action streamlining operations, aligning teams, building structure, and leading our people day-to-day. This is a player-coach role: you’ll get in the weeds early, but grow into a strategic leader who can help scale the company across markets.

ESSENTIAL JOB DUTIES AND FUNCTIONS

Team Leadership

• Lead and mentor cross-functional teams across operations, sales, support and marketing.
• Improve team productivity, accountability, and clarity of roles/responsibilities
• Support or lead hiring, performance management, and professional development

Operations & Execution

• Build and document repeatable systems and SOPs
• Own key performance indicators (KPIs) and reporting for sales and marketing.

Business Alignment

• Be the bridge between CEO’s strategic vision and team execution
• Lead weekly sales and marketing meetings and ensure progress against goals
• Drive collaboration between sales, marketing, guest support and owner relations.
• Help refine pricing models, fee structures, and internal processes
• Manage/implement software

Growth & Scale

• Support expansion into new territories with process readiness
• Take the lead on special projects, from tech implementations to partnerships
• Help prepare the company for capital partnerships, M&A, and future org design

Revenue & Performance

• Collaborate on dynamic pricing strategies and revenue calendar management (using PriceLabs, Wheelhouse, or similar)
• Monitor ADR, occupancy, RevPAR, and booking pace to identify opportunities and underperformance
• Support initiatives to drive additional revenue (e.g., linen fees, maintenance services, pest control upsells, insurance, product placement)
• Partner with marketing and finance teams to forecast and improve owner returns

COMPETENCIES

• You’ve led operations or teams in a fast-growing, entrepreneurial company
• You’re a builder at heart—strong with systems, but not stuck in bureaucracy
• You love people and process equally—comfortable leading a meeting or fixing a workflow
• You’re an assertive, proactive communicator who’s not afraid to lead
• You thrive with autonomy and ownership, and want a seat at the leadership table
• You are Tech-savvy and systems-oriented (AI knowledge, PMS, pricing tools, task management platforms)

EDUCATION AND QUALIFICATIONS

• 5–10+ years in operations, general management, or leadership roles
• Experience in hospitality, vacation rentals, property management, real estate, or service-based industries a plus - Luxury experience would be amazing.
• Familiarity with KPIs, financials, CRMs, PMS, and project management tools
• Ability to work flexible hours, weekend work required

COMPENSATION & BENEFITS:

Salary: $90,000 - $130,000 based on experience

Benefits:

• Medical/Dental
• PTO
• Car Allowance
• Phone Stipend
• Paid Holidays

Work Location: Remote

Schedule: Full Time, Monday – Friday with occasional Weekend hours