Director, Cloud Engineering

Upside, Washington, DC

Finally, there's an Upside to business travel

We are an ambitious, well-funded startup with plans to change a $1 trillion-dollar global industry. This is no ordinary startup. We have a proven management team that has done it before, done it before together, and done it before in the travel industry. The company is overflowing with fiercely intelligent people who have tons of energy and an upbeat view of the future. We all act like owners and we get a huge kick out doing great work and doing it fast. We like it even more when we come up with a fresh way to solve a problem. Above all, we are devoted to solving customer problems, because that’s at the center of everything we do.


  • You will lead, manage, and grow a technical team including SREs, data platform engineers, DBAs, and security team through strong technical and people leadership.
  • You will lead engineering operations, focused on ensuring performance, availability, reliability and security of the Upside Platform.
  • You will manage critical production environments using software development techniques and practices including configuration as code, automation, code reviews, configuration management, Objectives and Key Results (OKR’s), and weekly iterations/sprints.
  • You will own all processes, tools, and resources required to support high availability, cloud based, big data platforms.
  • You will develop collaborative relationships with cross-functional partners across the company, including Product, Data Science, Finance, Legal and Operations to mitigate operational risk across all systems, while delivering world-class experiences and meeting business objectives.
  • You will cultivate a modern DevOps culture and mindset throughout Upside’s engineering teams and establish performance metrics and processes to improve velocity and deliverability.
  • You will own the day-to-day health, uptime, monitoring, and reliability of our cloud infrastructure in AWS.
  • You will provide expert counsel and guidance to senior management on information and operational security and its impact across business strategy, programs, products and operations.


  • You have a B.S. or higher degree in Computer Science or 10-15 years of relevant experience.
  • You have demonstrated strong leadership, organization skills and people management skills, with at least 5 years of management experience.
  • You have 3+ years of production AWS experience, including but not limited to EC2, RDS, ElastiCache, S3, Auto Scale, ELB and AWS security best practices.
  • You have 3+ years of hands on operational experience in a high-volume or critical production service environment.
  • You have strong quantitative and analytical abilities with deep understanding of how to develop relevant metrics that not only track activity but also quantify the impact of operational initiatives on the financial, growth, and performance of the business.
  • You have strong technology skills to triage and provide solution and direction to the Operations team.
  • You have experience with container stacks and orchestration (Docker, Kubernetes, Mesos, ECS, etc), Infrastructure as a Code frameworks such as Terraform, CI/CD tools and production code deployments and Microservices architectures.
  • You have experience with and excellent understanding of PCI DSS.
  • You have strong vendor management and operations skills.
  • You have startup experience!
We love to ship. We’re completely on the CI/CD train, shipping code multiple times a day. We’ve developed a clustered container environment in AWS using Docker and Kubernetes to manage dozens of microservices written primarily in Node, Go and Python. Our web frontend is written in React/Redux and we’re building native iOS and Android apps that take full advantage of the powerful platforms they run on.  

We are positive, passionate, playful, and always pushing to be better. Our team is a hodgepodge of challenge seekers, travel gurus, startup junkies, and data-miners who see the big picture.

You are motivated by disrupting the norm.
You have a great sense of humor and take your profession seriously, but not yourself.
Your entrepreneurial spirit drives your bias for action.
You are all about constructive feedback - you can dish it out and you can take it.
You thrive in the frenetic energy of a startup.

Competitive salary + equity 
Full health, vision, and dental coverage
401K plan 
Open paid time off 
Dog-Friendly Office
Upside Travel is an equal opportunity employer and encourages people of all backgrounds, genders, ethnicities, abilities, and sexual orientations to apply. We are committed to being an inclusive place to work, while maintaining a workforce that represents the communities we serve.

About Upside

You deserve a better business trip. Upside is building a world-class team passionate about creating a product that will turn business travel from mundane to magical. This is no ordinary startup. We’ve already brought on some of the most passionate, intelligent and seasoned founding team members on the planet. Our founders started websites you’ve been using for years and are some of the most connected deal-makers in business. We are ambitious, well-funded and plan to change a $1 trillion global industry. If you're looking for challenging work that demands real thinking, bold action and big-time responsibility, then check out our available positions.


Want to learn more about Upside? Visit Upside's website.