SkyRun Vacation Rentals
July 12, 2021
Remote Position, United States of America
Job Type
$120,000 - $180,000 annual salary based on experience and qualifications


Job Title: Senior Software Engineer

Company Location: Remote position
(Quarterly visit to the Boulder, Colorado, headquarters)

Position type: Full-time

Company Overview:
SkyRun Vacation Rentals is rapidly growing and currently facilitates over 20,000 guest reservations annually and manages over 1000 properties across 35 of the most beautiful destinations in North America.  The technology platform that SkyRun has built to manage these reservations, properties, and locations, has grown to be one of the most advanced in the vacation rental industry. This position is a unique opportunity - a rare combination of “in on the ground floor” exposure with an already established Inc 5000 growth trajectory and in the sizzling hot vacation rental industry.

Position Summary:
SkyRun is seeking a Senior Software Engineer that will build and lead a team of development professionals tasked with delivering a best-in-class vacation management software platform that allows our local operations to manage their backend operations more efficiently and generate more homeowner income than any other vacation rental management company in the industry.  This position serves as a key role within SkyRun and is responsible for the functionality of our foundational software platform while bringing thought leadership to revolutionize it. You will partner across stakeholder organizations and be responsible for overseeing the design, development, maintenance, and continual improvement of SkyRun’s technology platform, as well as overall product innovation, evolution, feature development, scalability, and reliability.

This is a great opportunity for an ambitious, independent, experienced Senior Software Engineer who wants to help drive the evolution of how SkyRun disrupts the vacation rental industry. Success in this role requires direct hands-on-keyboard experience with building scalable, reliable, resilient software systems in Linux and PHP, with a special focus on leveraging Cloud Computing (especially AWS) to continue to improve the overall system.  The ideal candidate can balance their hands-on design/development time while also leading SkyRun’s small team of developers.

We are looking for someone to:

  • Own the ultimate success of our SkyTrax platform and IT systems, including design, implementation, maintenance, performance, security, availability, and recoverability
  • Design and build innovative new features to constantly improve SkyRun’s technical capabilities
  • Develop vendor and technology roadmaps to anticipate future information technology needs and identify solutions based on changing strategic directions and growth
  • Provide a comprehensive assessment of the technical and business fitness of organizations’ current IT systems
  • Ensure consistent professional services delivery of the IT team (domestic and offshore resources) through people leadership and hands-on work, as well as documenting and maintaining standards and procedures
  • Serve as a technical lead while effectively collaborating with internal teams
  • Provide technical expertise and professional experience to help develop Scopes of Work (SOWs) and Service Level Agreements to ensure they can be satisfactorily accomplished and that objectives are met
  • Oversee security of systems, networks, and enterprise information.
  • Conduct periodic audits and due diligence checks of security protocols, evaluating systems for vulnerabilities, and identifying and implementing patches for vulnerabilities.
  • Work with core stakeholders, business functional teams, and development resources to define deliverables

Team Leadership

  • Motivate the team towards a unified vision and provide strategic direction towards a best-in-class user experience vision.
  • Be hands-on and lead by example to promote high engagement, performance, and collaboration.
  • Have a demonstrated history of solving complex problems and an ability to communicate solutions efficiently and effectively.
  • Independent, self-starter who effectively prioritizes competing deliverables. Ability to be flexible in work schedule and to meet strict deadlines under minimal supervision


  • 5+ years of hands-on development experience as a Software Engineer
  • 3+ years in a Software Engineering Management role
  • Extensive development experience with PHP and Linux
  • Extensive experience and fluency with various web hosting stacks, especially LAMP
  • Familiarity with cloud compute platforms, especially AWS.
  • Experience migrating from single-server monolithic web hosting stacks to modular, cloud-based microservices is a plus.
  • Technical architecture design, experience, and fluency, enabling easy discussions with engineers
  • Bachelor’s degree in Information Technology, Engineering or related field preferred


  • $120,000 - $180,000 annual salary based on experience and qualifications


  • Generous PTO policy
  • Health insurance
  • 401(k), including company match
  • Basic life insurance policy
  • Long-term disability insurance
  • Fun and Wellness bonus
  • Paid volunteer days
  • Employee assistance program
  • Phone and internet allowance
  • Flexible schedule
  • Work from home - Quarterly travel to the headquarters office in Boulder, CO
  • Dog-friendly office
  • Additional employee-paid benefits are available through payroll deduction.