VP Engineering



Remote (USA timezones)

As VP Engineering, you will be responsible for building and scaling our engineering function with a focus on strategy, security, and scalability. You will work cross-functionally to ensure Scott's Cheap Flights is staying ahead of potential architecture and growth pitfalls within our infrastructure. Additionally, you will attract, empower, and inspire our engineering team. You will be a part of the Scott's Cheap Flights Leadership Team and will report directly to the CEO.

In the short term, you will:

  • Mentor and motivate our talented team of engineers and engineering leaders, empowering them to develop and deliver high-quality software
  • Identify and hire new teammates to effectively scale the team alongside the business in order to ensure capacity of the organization to deliver on the roadmap
  • Join the leadership team, bringing a fresh perspective, challenging our ways of thinking, and leveling up our technical expertise
  • Work cross-functionally to ensure and communicate clear prioritization of key features and project work and develop collaborative processes to enable efficiency
  • Lead and inspire the Engineering team to execute on scalable architecture and efficient product launches
  • Work alongside Product and Operations to define the technical strategy and hiring plan for our first-ever mobile application
  • Implement processes and ways of working that enable the team to do their best work

In the long term, you will:

  • Develop a strategic and technical roadmap, identifying and solutioning against potential pitfalls, for the organization to reach 100M+ members
  • Maintain best-in-class data security and privacy practices, ensuring compliance and keeping our members in mind with every decision
  • Partner with Marketing & Product to launch consumer experiences that are available, scalable, performant and drive substantial growth for the business

What you know:

  • You have extensive experience building highly scalable systems for multiple major consumer software organizations
  • You have proven experience managing managers and scaling an engineering team in a fast-growth environment, ideally with experience more than doubling the size of a team.
  • You can identify when and how we hire full-time employees versus contractors across multiple streams of work
  • You understand how to motivate and inspire a team in a remote-first environment
  • You are an expert coach, leading by example with deep technical expertise
  • You know when to prioritize speed vs. quality, ensuring quality architecture on our most critical systems while shipping product quickly to provide value to customers.
  • You have a commitment to diversity, transparency, inclusivity, and accountability in everything you do
  • You like to stay two steps ahead of the business in order to identify future pitfalls and scale effectively
  • You have built and managed an excellent QA operation consisting of both manual processes and automated testing with high code coverage
  • You have launched native applications on both iOS & Android
  • You have led efforts to build a modern consumer web experience using Single Page Application frameworks
  • You have clear & concise communication skills, both written and verbal
  • You are legally authorized to work in the United States

Why you might love working here:

  • 100% remote work environment, so go ahead and bring your dog to work or wear your PJ's to the office!
  • Open vacation policy, with a 3 week minimum!
  • Comprehensive health, vision, and dental insurance
  • 401(k) with a 5% match
  • Up to 12-weeks of paid family leave
  • Monthly wellness reimbursement
  • Continuing education & development reimbursement
  • Yearly team retreat (In 2019, we went to Riviera Maya. Last year, we had a daily costume contest and went virtual!)
  • Challenging problems to solve and an awesome team to collaborate with every single day

We want you to bring your authentic self to work every single day. We accept you for who you are and consider everyone on an equal opportunity basis without regard to ancestry; age; appearance; color; gender identity and/or expression; genetics; family or parental status; marital, civil union, or domestic partnership status; mental, physical, or sensory disability; national, social or ethnic origin; past or present military service; sexual orientation; socioeconomic status; race; religion or belief.

If you require a reasonable accommodation or assistance for any part of the interview and employment process, please contact us at and let us know the nature of your request.