Head of Operations & Growth

Head of Operations & Growth at O'Neal Vacation Rentals | Santa Cruz, CA O'Neal Vacation Rentals is a fast-growing vacation rental management company based in Santa Cruz County, managing 90+ unique homes across the region. We are not a traditional hospitality company, and this is not a traditional hospitality management role. We operate like a modern service-based startup: highly collaborative, fast-moving, systems-driven, and deeply focused on delivering exceptional homeowner and guest experiences while scaling intelligently. We are looking for a highly organized, operationally sharp, people-oriented leader to become a key partner in helping us grow the business over the next phase. Position Summary The Head of Operations & Growth is responsible for overseeing and improving the day-to-day operations, homeowner experience, guest experience, onboarding, and growth functions of O'Neal Vacation Rentals. This role serves as a key operational leader within the company and works closely with the founders to ensure the business operates efficiently, scales sustainably, and maintains high standards across all departments. The Head of Operations & Growth is expected to lead through systems, accountability, communication, and team development while helping the company continue to grow operationally and financially. This position is both strategic and hands-on. While the role is primarily office- and systems-based, the employee is expected to support operational needs in the field when necessary. This role is ideal for someone who: thrives in operational leadership loves improving systems and solving problems can lead teams through accountability and clarity enjoys both strategy and execution can balance growth with operational excellence is energized by building something meaningful alongside founders This person will work closely with the founders as a true operational integrator of the business. Overseeing day-to-day operations, guest experience, homeowner success, onboarding, and growth initiatives while helping the company scale sustainably. What This Role Is NOT This is not a traditional hotel GM role. You will not spend your day physically inspecting properties, walking floors, or managing through constant in-person oversight. Instead, this role is focused on: building scalable systems leading people effectively leveraging technology and processes improving accountability driving KPIs identifying operational bottlenecks helping the company grow without operational breakdowns That said, we do value leaders who are willing to jump in when needed. Whether that's helping solve a guest escalation, visiting a property issue, supporting the team during peak demand, or stepping into operational problem-solving firsthand. Core Responsibilities Operations Leadership Oversee daily operations across guest support, field operations, maintenance coordination, and vendor management Improve and optimize operational systems and workflows Build scalable processes that reduce founder dependence Monitor KPIs and proactively identify operational issues before they escalate Ensure consistent quality standards across the portfolio Team Leadership & Accountability Lead and support team members Create a culture of ownership, accountability, communication, and continuous improvement Coach team members while also holding high standards Help identify staffing gaps, process breakdowns, and opportunities for organizational improvement Maintain alignment and collaboration across departments Growth & Client Experience Oversee new listing onboarding and Client management Support sales and growth efforts, including converting and onboarding new homes Ensure operational readiness as the portfolio grows Build long-term Client trust and retention Guest Experience Oversight Ensure excellent guest experiences at scale Review guest feedback trends and operational pain points Lead service recovery on higher-level escalations when necessary Improve systems that drive review quality and guest satisfaction Strategic Partnership with Founders Collaborate closely with founders on business priorities and company growth Help translate high-level goals into operational execution Bring ideas, initiative, and operational clarity to the business Operate with a high level of ownership while maintaining strong collaboration and communication Who You Are You are: highly organized and operationally minded calm under pressure adaptable and solutions-oriented emotionally intelligent and collaborative systems-driven without becoming overly rigid capable of balancing details with big-picture thinking comfortable with ambiguity and growth low ego, high accountability You know how to: lead without micromanaging create accountability without creating fear improve systems without overcomplicating them leverage people, process, and technology effectively balance operational excellence with growth You genuinely enjoy: solving messy operational problems building better ways of doing things developing people creating consistency at scale helping businesses evolve Experience We Value We are open to candidates from a variety of operational leadership backgrounds, including: vacation rentals / STR hospitality service operations property management startups field operations home services multi-unit operations logistics or operationally complex businesses Hospitality experience can be helpful, but we care far more about operational leadership, adaptability, communication, and systems thinking than traditional hotel management experience alone. Qualifications Required 5+ years of leadership or operational management experience Strong organizational, communication, and problem-solving skills Experience managing teams, workflows, and operational processes Ability to lead in a fast-paced and evolving environment Strong accountability and follow-through Ability to prioritize and manage multiple competing demands Proficiency with technology platforms, communication tools, and operational systems Preferred Experience in hospitality, vacation rentals, property management, service operations, or operationally complex businesses Experience with KPIs, reporting, and operational performance tracking Experience leading distributed or field-based teams Experience in scaling operations or process improvement initiatives Compensation & Growth Competitive salary + performance incentives Opportunity to help shape and scale a growing company High visibility and direct collaboration with founders Meaningful long-term leadership opportunity Physical & Operational Requirements This role is primarily office and operations-based, but it does require occasional on-site support and field involvement. Physical Requirements Ability to travel locally throughout Santa Cruz County as operational needs require Ability to sit, stand, walk, and use a computer for extended periods of time Ability to walk properties and navigate stairs Ability to occasionally lift and carry items up to 25 pounds Ability to respond to operational issues that arise outside standard business hours Work Environment This role operates in a hybrid office and field environment. The position is primarily office-based with occasional on-site operational support and property visits as needed. The role requires flexibility, adaptability, and the ability to operate effectively in a fast-moving and evolving business environment.

Pay:

$100,000.00 - $140,000.00 per year

Benefits:

401(k) Employee discount Health insurance Paid time off Professional development assistance Application Question(s): This role is a blend of operations leadership, team management, homeowner/client relationships, and growth. Tell us about a role where you were responsible for improving operations while also balancing customer/client experience and business growth. What did you own, what did you change, and what were the results? Our company operates more like a fast-moving startup than a traditional hospitality business. We rely heavily on systems, communication, accountability, and technology, not constant in-person oversight. Tell us about a time you built or improved a process that helped a business scale more efficiently. What problem were you solving, and how did you approach it? This role requires someone who can lead independently while still collaborating closely with founders and managers. Describe the best working relationship you've had with ownership or executive leadership. What made it successful, and what leadership style helps you do your best work?

Work Location:

In person