Lead DevOps Engineer

Full Time
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The Company

At Olive our mission is to help investors achieve financial goals with more control than ever before. We’re unlocking the power of listed options to give retail investors the investment outcomes they want. 

There are over 80M US adults with non-retirement brokerage accounts, but what to invest in has never been a more difficult question. With bonds yielding negative real returns, stocks trading at all time high, and volatility likely to be more frequent, options can help.

Investing in options has been an overwhelmingly poor experience for most investors. Greeks, complex math, and chains of data make options seem difficult, risky, and ultimately inaccessible to most investors. Banks, insurers, and asset managers have built a $1 trillion market selling structured investment outcomes to wealthy people in the forms of structured notes, annuities, and ETFs. We want to level the playing field and give every investor the ability to control their financial outcomes.

We are headquartered in Hudson Yards, NYC though our team is made up of a global team of mostly contract designers, engineers, data scientists, financial analysts, and product managers who are working toward a common goal of making outcome investing easy and accessible. We are currently building out our full-time founding team, and are excited to find our first 10 employees.

The Role

We are looking for a thoughtful and experienced DevOpsLead to help us level up the Olive application infrastructure, internal tools, and development environments. They will lead hands-on work across diverse responsibilities ranging from problem-solving, system and feature design, making designs into action plans, and staff mentoring. The DevOps Lead also plays a key role in partnering with engineering to evolve our long-term technical strategy and guide the team through the realization of these solutions. This individual will work closely with other teams across the organization, so excellent communication skills and a collaborative mentality are crucial. In addition they will get to work with the latest technologies, while helping to provide strategic technical advisory and complete software delivery automation solutions. This is a technical leadership position that does not include people management in its current scoping, though there is longer-term potential for this.

What You’ll Be Doing
  • Take a leadership role in multiple simultaneous high-impact projects, including facilitating design discussions, breaking down plans into work items, and mentor team members.
  • Architect, build, and maintain tools fora self-service infrastructure that improves developer efficiency and code reliability.
  • Help scale and solidify Olive’s production application infrastructure while improving monitoring and application performance management.
  • Manage the team’s backlog and advocate for technical initiatives.
  • Communicate clearly in verbal and written forms, from peer training to design documents.
  • Explore alternatives and quickly prototype to validate hypothetical architectures or solutions.



Minimum Qualifications:

  • 6+ years of DevOps, infrastructure, or site reliability experience.
  • Experience with technical leadership/ownership of a scaling DevOps function.
  • Demonstrated competence deploying applications/tools into production cloud environments with configuration management tools such as Kubernetes, Terraform.
  • Understanding and experience with GCP best practices.
  • Strong hands-on experience with tools such as Jenkins to enable CI/CD.
  • Relevant scripting or programming skills(Bash, Python, Go, Ruby, etc.)
  • Solid understanding of infrastructure security (https, SSH, 2FA, etc.) and modern networking for private cloud and public Internet services.
  • Familiarity with database performance management and  managed data storages(PostgreSQL, Big Query).


Preferred Qualifications:

  • GKE
  • Experience working for a high growth FinTech startup.
  • Experience working remotely in a distributed team.

Olive is Virtual First

We believe that the future of work isVirtual First, meaning our Team will primarily work remotely with hubs in NYC, and Florida for in-person collaboration and team events. We welcome applications from across the United States, as long as you’re open to travel to a hub as and when needed.

Our company culture supports flexible working schedules with an open Paid Time Away policy and gives all team members the opportunity to travel and work remotely with great people. If you think you have the skills and passion, we’ll give you the support and opportunity to thrive in your career. If you would like to be considered for the role, we would love to hear from you!

We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status.

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