A Little Bit About Us
We offer exceptional vacation homes across the country’s most celebrated ski towns and coastal retreats. Each property is carefully selected, locally managed, and held to an uncompromising standard of care. We live and work in the communities we serve, which means every stay comes with generous local knowledge, genuine hospitality, and the confidence that what you booked is exactly what you’ll find.
Benefits
We’re proud to offer a competitive benefits package designed to support our employees both at work and beyond. Benefits and eligibility may vary by position and are subject to change. Full plan details and terms will be provided during onboarding.
Health, Dental & Vision Insurance
401(k) with Company Match
Paid Time Off (PTO)& Holidays (non-exempt employees)
Paid Flexible Time Off & Holidays (exempt employees only)
Paid Sick Leave
Benefits are subject to the terms and conditions of the applicable plan documents, which govern in the event of any discrepancy. The Company reserves the right to modify, suspend, or terminate benefit plans and programs at any time.
About This Job
First Chair is a property management company with HOA management responsibilities, running a modern, fast-moving technology stack across guest operations, owner relations, and internal systems. We're in the process of insourcing core IT and security functions from our managed service provider, and this role is the linchpin of that transition.
We're looking for a hands-on, senior technologist who can own three things at once: the security posture of the company, the infrastructure and DevOps environment that supports our in-house software (built on Google Cloud), and the helpdesk function that keeps every employee productive. This is a builder's role — you'll be standing up tooling and processes from a relatively blank slate, not maintaining a mature environment.
Compensation + Schedule
- $120,000 - $140,000 annual less payroll deductions and all required withholdings
- Typically Monday - Friday schedule
- MUST be located in the USA. We cannot employ outside of the USA or sponsor. Mountain Standard Time (MST highly preferred).
- Fully remote work environment with reliable internet connection.
- Typically a Monday - Friday workweek with expectations to be flexible to support the needs of the business.
- Weekends and holidays may be required
Essential Job Functions
- Security: endpoint detection & response (EDR), patch management cadence, email/identity security, MFA and access controls, vulnerability management, and incident response — building toward a defensible security program without an outsourced MSP.
- DevOps & cloud infrastructure: stand up and manage our independent hosting environment (Google Cloud), own CI/CD and deployment practices for internally built tools, and manage uptime, backups, and disaster recovery for systems we run ourselves.
- Helpdesk & end-user support: own the transition of day-to-day IT support in-house, including ticketing/PSA tooling, onboarding/offboarding processes, and device management (MDM) across a MacOS/Google Workspace environment.
- Networking & endpoints: manage IT networking equipment across sites, endpoint security baselines, and the credential/password vault used company-wide.
- Vendor management: hold direct relationships with Google Workspace, security tooling vendors, and any remaining specialist providers — no reseller layers between First Chair and its core licensing.
- Documentation & continuity: build the runbooks, network diagrams, and escalation paths that don't currently exist outside a departing MSP's head.
- Collaborate with cross-functional teams and stakeholders to align departmental goals with broader organizational strategy. Represent the team in leadership meetings and communicate strategic decisions effectively to direct reports.
- Support continuous improvement initiatives by analyzing program performance, identifying bottlenecks, and implementing process optimizations. Stay current with industry trends, best practices, and emerging technologies relevant to the function.
- Other duties as assigned because every day is different in hospitality!
Skills + Qualifications
- Experience working in hotel, hospitality, vacation or similar industry is highly preferred.
- College education is strongly preferred, though we recognize that great talent comes from many different paths.
- 8+ years of progressive experience across IT operations, information security, and/or DevOps, ideally including time as the senior or sole technical owner at a small-to-midsize company (not just a large team seat).
- Hands-on cloud experience, Google Cloud strongly preferred (GCP compute, storage, IAM, networking); AWS/Azure equivalent experience also considered.
- Practical security chops: EDR/SIEM tooling, MFA/SSO, patch management, and incident response — able to both operate the tools and explain the posture to non-technical leadership.
- Experience managing helpdesk/ticketing operations and end-user support at scale (roughly 400+ users), including onboarding/offboarding workflows.
- Comfort owning infrastructure independently — this role is being built specifically to reduce reliance on outsourced IT, so self-direction matters more than following an existing playbook.
- Bonus: experience transitioning a company off a managed service provider (MSP) and building an internal function from scratch.
- Bonus: familiarity with a MacOS + Google Workspace environment, and with property management, hospitality, or HOA industry systems.
- Prior product and / or program management level experience in a similar industry or field.
- Tech-savvy with experience using various digital systems and applications and comfortable using mobile apps, tablets, and various software platforms.
- Communicates clearly and confidently—whether it's over email, on a video call, or in person—and can build strong connections with both team members and clients
Workplace Environment + Physical Requirements
- MUST be located in the USA. We cannot employ outside of the USA or sponsor.
- Fully remote work environment with reliable internet connection.
- Typically a Monday - Friday workweek with expectations to be flexible to support the needs of the business.
This job description does not identify every requirement of the position. First Chair may change position requirements, responsibilities, and work environment at any time with or without notice.
Some positions may require that you drive a personal vehicle and/or company vehicle for work purposes. Employees who are required to drive a personal vehicle must have reliable transportation, a valid driver’s license, and be at least 18 years of age. Employees who are required to drive a company vehicle must have a valid driver’s license, be at least 21 years of age, and have been a licensed driver for no less than 3 years.
An offer of employment for this role will be contingent upon the successful completion of a background check.
