Head of Engineering

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 senior, hands-on, engineer to lead, mentor and grow the team building our options trading platform and applications. We are working on V2.0, which will involve building new features from the ground up, as well as elevating our current offerings. The ideal candidate will have a track record of leadership and technical excellence in designing and delivering reliable, scalable solutions. This role will be involved in setting high level goals and ensuring the overall success of engineering initiatives. This includes prioritizing well-reasoned ideas that improve our engineering operations and reward the people who bring those ideas to light. A cursory knowledge of options trading is a requirement, as this person is expected to learn the options trading space and become an SME in a short time.

Our current tech stack - GCP, GKE, Kubernetes, Docker, Kafka, BigQuery, Looker, Python, Go, React, React Native

What You’ll Be Doing
  • ​​Architect decisions to resolve complex technical problems.
  • Transition between high-level strategy and day-to-day implementation.
  • Deliver complex, real-time internet-scale systems involving machine learning and AI; preferred if in finance or trading domains.
  • Proactively identify and remove roadblocks for your team.
  • Manage technical debt and prioritize technical investments while delivering on product commitments.
  • Collaborate with stakeholders acrossProduct, Data & Analytics, Marketing to develop a clear, robust technical roadmap, thinking strategically and diving deep.
  • Promote continuous delivery and ownership of automated testing by developers.
  • Increase velocity and lower change failure rates by continuously improving the software development process.
  • ​​Set clear expectations for team members; solicit, synthesize and deliver timely, constructive feedback, ensuring your team consistently makes and meets commitments.
  • Review code and architectural designs while advocating best practices.


Minimum Qualifications:

  • 8+ years of professional software development practice (web and mobile).
  • 3+ years of technical leadership.
  • 1+ year of people management.
  • Hands-on experience designing and building technical architecture to power high availability platforms.
  • Passionate about inventing and delivering customer-focused solutions to ambitious and ambiguous challenges.
  • Willing to dive into building new systems and processes as needed.
  • Able to build effective relationships with stakeholders, product partners, engineers, and leadership.
  • Excellent written and verbal communication skills, demonstrated through experience working with technical and non-technical teams.
  • Personal or professional experience with options trading.


Preferred Qualifications:

  • Experience working for a high growth FinTech startup.
  • Experience working remotely in a distributed team.
  • Experience building trading platforms.

Olive is Virtual First

We believe that the future of work is Virtual 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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