Director of Engineering


Job Description / Skills Required

West Coast preferred

Espresa is the only personal benefits platform that delivers a global and all-in-one experience for HR, people teams, and employees. With a core focus on Lifestyle Spending Accounts (LSAs) and a complimentary, modular suite of solutions focused on total wellbeing, recognition, and community, Espresa powers Great Places to Work® while making heroes out of HR teams.

Join our growing team of tenacious builders, designers, and people igniters, and help transform the industry of personal benefits for good.

The opportunity:
Basically, you are a superhero (no cape required). Here is what we’re looking for, and, as with any growing company, this is not intended to be all-inclusive. We’re innovative, and you have an opportunity to help design this role and grow it. 

As a Director of Engineering, you will lead software development efforts. Your role will involve making key architectural decisions, driving the adoption of best software design and security practices, and leading a global team of talented engineers. Your deep expertise in Python, Django ORM, and familiarity with Angular will be crucial in guiding our technical direction. 

Here’s the base:

  • Strategic technical leadership: Lead a software engineering team, setting technical direction and ensuring the implementation of best practices across all projects. 
  • Architectural oversight: Oversee the design and architecture of scalable software solutions and APIs, ensuring they align with business objectives and technical requirements. 
  • Team management: Mentor and manage a team of engineers and technical leads, fostering a culture of excellence, innovation, and continuous learning. 
  • Hands-on development: You are comfortable with diligently reviewing code, contributing to coding and development tasks where needed, and demonstrating best practices by example. 
  • Cross-functional collaboration: Work closely with Product Management, Design, and QA teams to ensure cohesive and efficient software delivery. 
  • Quality assurance: Ensure the delivery of high-quality, secure, and efficient software products by maintaining a strong focus on code quality and modular design. 
  • Dev ops: Ensure that software deployment is efficient, secure, and meets SLAs. 


  • At least ten years of professional software engineering experience, with a significant portion in a leadership role. 
  • Proven Python and Django ORM expertise and familiarity with front-end technologies such as Angular. 
  • Strong experience in designing and architecting APIs and complex software systems. 
  • Demonstrated leadership skills with the ability to guide and inspire a technical team. 
  • In-depth knowledge of software design principles, architecture, and security best practices. 

We don’t expect you to know all this. We know you should be able to pick up much of this as needed. However, if you have prior experience with these, please mention them!

Nice to Have: 

  • Comfortable with CI/CD tooling and DevOps 
  • Experience with ML infrastructure, recommendation engines, authentication protocols (SAML 2, OAuth 2, OpenID Connect, etc.), file transfer protocols (SFTP with PGP, HTTPS POST with different mime encodings)
  • Experience integrating with platforms like Workday, Slack, Teams, and Shopify

Espresa’s benefits

Espresa offers a comprehensive benefits package that is competitive with Silicon Valley/Bay Area employers, including health, retirement, a Lifestyle Spending Account, generous PTO, and more.

We are an equal opportunity employer and do not discriminate on the basis of race, religion, national origin, gender, sexual orientation, age, veteran status, disability or any other legally protected status.

For US Based Candidates: Pursuant to the San Francisco Fair Chance Ordinance, we will consider qualified applicants with arrest and conviction records.

We are committed to providing reasonable accommodations to applicants with disabilities.

Show us you and how our mission and vision shine in you. We welcome wonderful, kind, and bright humans!